A PTO-Friendly Weekend in Dublin: 2.5 Days of Craic, Coffee & Culture
I had exactly 2.5 days in Dublin and exactly one single day of PTO to make it happen. And somehow? It was perfect. If you’re a corporate girly (or guy) who wants a fun, low-stress, mid-budget city break that delivers history, pub culture, and literary charm in a compact, walkable package… Dublin is about to be your new favorite fling. Small in size, rich in soul, and the kind of place that makes you feel instantly part of the story, Dublin will serve you cozy vibes, witty banter, and a pint of something dark faster than you can say sláinte.
Here’s my exact long weekend itinerary (plus a few things I’d 100% skip next time).
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🗓 My 2.5-Day Dublin Itinerary (PTO-Friendly Edition)
Day 1 – Friday PM: Arrival & First Impressions
Land around midday and hop on the Aircoach into the city. It’s fast, easy, and you can people-watch on the way in. Check into a boutique hotel like The Alex or The Dean or – my favourite – into Motel One* think stylish, central, and “corporate chic meets cozy.” Stretch your legs with a walk through St. Stephen’s Green. Depending on where your hotel is, you’ll enjoy a walk through the city centre at the same time. Did you discover the Powerscourt Townhouse yet?
If you still have time, get into the Post Office for some Easter Rising history lessons.
Dinner + first Guinness at The Hairy Lemon (quirky) or The Brazen Head (Ireland’s oldest pub). Bonus points if you end the night chatting with locals at the bar.
Day 2 – Saturday: Culture & Craic
Breakfast at Queen of Tarts. Trinity College Library, aka Dark Academia heaven( Book ahead). The smell of old books? Intoxicating. Right across is the Irish Whisky Museum. Walk in for a nice history and whisky tasting lesson.
Wander Grafton Street and don’t miss Sweny’s Pharmacy (yes, the one from Ulysses).
Afternoon choice: Guinness Storehouse for the panoramic Gravity Bar view (and the touristy action) or Liberties Distillery if even more whiskey is more your speed.
Stop at St. Patrick’s Cathedral and enjoy the gardens.
Evening: Live music & storytelling at The Cobblestone or Whelan’s. Order a pint, get lost in the music.
Day 3 – Sunday: Slow & Sweet
Brunch at Tang or Bibi’s Café. Stroll along the River Liffey or explore Dublin Castle.
Before heading to the airport, stop my Kilmainham Gaol for even more history.
💼 PTO Tip:Flying from Europe?
Taking just Friday off gets you 2 nights of fun. Can swing Monday too? You’ll have a more relaxed return. Either way, Dublin is a short-haul, high-reward win.✨
What I Loved
The warmth of the people. You’ll end up chatting with strangers constantly. And not just because I’m a red head and people believe me to be local until I open my mouth.
The literary roots, if you’re into Dark Academia vibes like me, you’ll be in heaven.
The walkability, no taxis needed unless you’re feeling fancy.
What I’d Skip Next Time
Temple Bar: fun once, but there are cozier, less touristy, less expensive pubs that feel more authentic.
Over-scheduling: Dublin works best when you slow down and just… be. Let the street musicians, pub conversations, and hidden corners find you.
Want to Travel Like a Pro?
Before every quick getaway, I map out my weekend so I’m not wasting precious hours deciding what to do. I even have a 2-day city break template that keeps flights, transport, and food spots in one place. Seriously, it saves so much brainpower.
Final Word:
Dublin isn’t a place you just visit. It’s a place you chat with, toast with, and carry home in your chest. And yes, you can do all that on one day of PTO.
Feeling burnt out from endless meetings and Zoom calls? September is the perfect time for a mental reset trip in Europe. The summer crowds have thinned, prices drop, and a cozy autumn vibe takes over the continent. In fact, more travelers are embracing September travel than ever. 22% of Europeans are eyeing trips this month, drawn by better weather, lower costs, and fewer crowds. As a 30–45 year-old corporate professional, you deserve a soul-soothing break.
So pack your scarf, your favorite leather-bound notebook, and maybe a spare memory card , we’re going on a “Europe mental reset trip” through some of the continent’s most moody, intellectual cities! ✈️
In this guide, we’ll explore 7 dark academia-inspired European cities perfect for a September escape. Think ivy-draped libraries, winding cobblestone alleys, candlelit cafés, and autumn leaves swirling around Gothic spires. Each destination comes with mid-budget friendly hotel picks (from charming boutiques to familiar chains like Marriott, IHG, and Hyatt at ~€100–€250/night), solo travel tips (safety, transit, walkability), offbeat attractions to avoid the crowds, and even pointers on using your Amex, Chase, or Bonvoy points to save money. We’ll keep it friendly, funny, and warm, like an old friend dishing out travel advice over coffee (or perhaps a pint of Guinness 😉). Ready to recharge Dark-Academia-style? Let’s go! 🎒✨
This post contains affiliate links. By clicking on the link I may earn a commission to no extra cost to you. Links are marked „*“.
For a mix of intellectual charm and hearty fun, you can’t beat Dublin in the fall. This city blends moody academia with the warm soul of Ireland. At Trinity College, the 18th-century Long Room library will take your breath away, two levels of ancient books under a vaulted wooden ceiling, complete with the scent of aged parchment and dust motes dancing in sunbeams. It’s basically a dark academia pilgrimage site (don’t miss seeing the Book of Kells exhibit too for some illuminated-manuscript magic).
Outside, Dublin’s autumn brings misty mornings and the occasional soft rain (“a good excuse to duck into a pub” as the locals say!). Literature is everywhere, from James Joyce quotes on plaques to the heritage bookstores along the River Liffey.
Offbeat Charm: After the must-do’s (Trinity, St. Patrick’s Cathedral, maybe the Guinness Storehouse for some craic), discover Dublin’s quieter corners. Tuck into Marsh’s Library near St. Patrick’s. It’s one of Europe’s oldest public libraries (1707) and often overlooked. Creaky oak bookcases, chained books, and zero crowds , you might feel like an 18th-century scholar here. Wander the Georgian streets of Merrion Square where Oscar Wilde’s childhood home stands (a statue of Wilde lounges in the park, as witty and carefree as his writing). In the evening, skip the over-touristy Temple Bar pub hub and head to Davy Byrne’s or The Stag’s Head . Historic pubs where Joyce and other writers drank.
Pro tip: Grab a seat by the fire, order an Irish stew or a pint of Guinness, and you might hear live traditional music or at least some colorful local storytelling.
Solo Travel Tips:
Dublin is very welcoming to solo travelers. The Irish will chat your ear off if you’re up for conversation. English-speaking, of course, so no language barriers. The city center is walkable; you can stroll from Trinity to Dublin Castle to Grafton Street easily. Public transport includes buses and the LUAS tram; they’re safe and convenient if needed (like getting out to the Kilmainham Gaol or Phoenix Park).
Safety: Dublin is generally safe, with the usual city caution. Watch for pickpockets in crowded areas and mind your belongings after a couple pints. Late at night, stick to well-lit central areas, the Temple Bar district can get rowdy (and pricey) after dark, so consider enjoying the pub culture in slightly quieter neighborhoods like Rathmines or Smithfield if you prefer a mellower vibe.
Stay:
Dublin has a range of mid-budget accommodations. For boutique lovers, The Dean Dublin* is a trendy option: modern design, a cool rooftop bar, and a fun music theme (there’s a record player in your room with some vinyls!). It’s around €200/night and gives a local, creative flavor.
For chain comfort, check out Hyatt Centric The Liberties* Dublin, a new 4-star in the heart of the Liberties area. Rooms are often ~€180, and you can use Hyatt points (~15,000 points/night, a solid deal). It’s walking distance to St. Patrick’s and has a great breakfast to start your day.
Marriott loyalists might try the Moxy Dublin City* in downtown, a playful, boutique-style Marriott property. It’s Ireland’s first Moxy, with a 24/7 bar and stylish lobby, usually well under €200.
Fun fact: The Moxy is near Trinity and Temple Bar, and Moxy even notes that Dublin’s literary heritage surrounds you, with writers, artists and intellectuals having flocked to these streets for centuries. So you’ll be in good company (past or present)!
I, personally love the Motel One* Hotels in every city. They are a design hotel chain, that focuses on local history and culture. I loved our room in Dublin and I would have packed that hotel bar into my luggage if it had fit.
Points & Perks:
Leverage those credit card rewards here. Chase Ultimate Rewards transfer to Avios can book you a flight directly into Dublin (Aer Lingus is an Avios partner, often with low surcharges). Once on the ground, your Amex Platinum card’s Global Entry benefit will speed you through US pre-clearance on the way home (Dublin does US customs pre-clearance, a huge time-saver).
For hotels, Hyatt’s partnership with Chase UR means you could stay at the Hyatt Centric for free if you have some points banked. And if you hold a Marriott Bonvoy free night certificate, the funky Aloft Dublin City (Marriott) is another option around 30k points that could be fully covered. Use those savings to treat yourself to a nice meal at a literary pub or to buy that signed first-edition novel you spotted!
Ghent, Belgium – Medieval Mystery by Candlelight 🕯️📜
Ghent’s enchanting riverside at twilight, fewer tourists than Bruges, but equally fairytale-like with a moody twist.
Why Go:
Picture a medieval city with canals, gothic spires, and virtually no tourists clogging the streets, that’s Ghent in a nutshell.
Often overshadowed by its pretty neighbor Bruges, Ghent is a hidden gem beloved by those in the know (and apparently 55% of Europeans now prefer such lesser-known spots to avoid overtourism). The city is less crowded than Bruges but just as enchanting, with old stone buildings, flickering lantern-lit lanes, and grand university halls imbued with centuries of scholarship. In autumn, Ghent’s tree-lined canals blaze with color, and a slight fog might roll in over the Lys River at dawn, adding to the mystery.
If you crave dark academia vibes, Ghent delivers with a touch of Flemish coziness.
Offbeat Charm: Start at the Boekentoren (“Book Tower”), Ghent University’s modernist tower library. It holds rare manuscripts and has a panoramic view of the city, a pilgrimage for architecture and book nerds alike. Next, visit St. Bavo’s Cathedral not just for the famous Van Eyck painting, but also for the eerie crypt below, wonderfully chilling and quiet. Meander through the Patershol district, a medieval quarter of narrow alleys now filled with quirky cafes and galleries; at night, lanterns cast golden light on the cobbles. Ghent even has a castle in the city center – Gravensteen Castle – complete with a torture museum (talk about getting dark!). Go in the evening for atmospheric vibes and maybe a ghost story or two.
And if you’re a fan of academia history: the Ghent University Aula is an impressive neoclassical hall often open for events. Poke your head in to imagine attending a 19th-century lecture there.
Solo Travel Tips:
Ghent is compact and extremely walkable (or bikeable – Flanders loves cyclists!). As a solo traveler, you’ll find it safe and easy to get around. The city center is pedestrian-friendly, and you can rent a bike if you want to live like a local student. Many locals speak excellent English, but throwing in a “dank u” (thank you) in Flamish will earn you a smile. Public transit includes trams and buses that connect the train station and outskirts, but within the historic center you likely won’t need them.
Safety: Ghent is very safe; standard awareness is all that’s needed. Perhaps the biggest “danger” is getting lost in picturesque lanes – but hey, that’s half the fun. If you’re out late, the area around Korenmarkt (main square) stays lively with students, and you can always pop into a “brown café” (cozy pub) if you need a break or some company.
Stay:
To fully soak in the atmosphere, consider 1898 The Post,* a boutique hotel set in Ghent’s former main post office building (a gorgeous Neo-Gothic gem). With only 38 rooms, it’s intimate and styled with vintage decor. You’ll feel like you’re staying in a Victorian writer’s private club. It also houses The Cobbler cocktail bar, one of the best in Belgium (don’t miss a nightcap there under the twinkling chandeliers). Rates hover around €200, but the experience is worth every penny.
For a chain option, the Ghent Marriott Hotel sits right on the canal at Korenlei and blends a modern hotel into a row of historic facades. You get the reliability of Marriott with a setting that’s anything but cookie-cutter, the lobby has a giant glass atrium and exposed brick from the 15th-century house it’s built into. Rooms (from ~€160) often have river views. And yes, Marriott Bonvoy points are welcome – about 25,000–30,000 points per night. Bonvoy elites even get free breakfast in the riverfront restaurant, fueling you for long walks.
Points & Perks:
Getting to Ghent can be part of the fun: fly into Brussels (which is easily done on points via United or American Airlines miles) and then take a 30-minute train to Ghent. No flights needed within Belgium, trains and trams do the trick. If you have a Eurail pass or just a ticket, Ghent is on the main line between Brussels and Bruges.
For hotels, consider using a Marriott Free Night Award from your Bonvoy credit card. The Ghent Marriott is a great way to redeem it without high-category prices. Also, if you’re a Chase Sapphire Reserve holder, you could book your hotel through the Chase travel portal using points (at 1.5 cents value), sometimes a good way to use those UR points if you’re short on Bonvoy.
Finally, treat yourself to a Belgian waffle or three, not a points tip, just life advice. You’re in Belgium, after all!
Cambridge, England – Scholars, Punts & Autumn Light 📚🍂
Why Go:
If Oxford is the brooding novel hero, Cambridge is the poetic dreamer. Home to one of the world’s most prestigious universities, this city hums with intellectual energy and history dating back to 1209. In September, the student term is about to begin, so the cobbled lanes and collegiate courtyards buzz with quiet anticipation. Add in the soft golden light over the River Cam, and it’s like stepping straight into a watercolor painting.
You’ll wander past Gothic chapels, lush lawns, and secret gardens and possibly overhear a debate about astrophysics over coffee.
Offbeat Charm:Skip the packed King’s College tour and opt for a punting trip on the Cam, preferably with a guide who peppers the journey with local lore. Visit The Wren Library at Trinity College (free at set times), which houses Newton’s own annotated copy of Principia Mathematica. For something quirkier, explore the Cambridge Museum of Zoology — yes, there’s a whale skeleton hanging from the ceiling. And if you want a cozy, candlelit drink, slip into The Eagle, the pub where Crick and Watson announced their DNA discovery.
Solo Travel Tips:
Cambridge is compact and walkable; you can explore most of it on foot. Buses connect the train station with the center, but strolling in via Mill Road is a treat in itself. Safety-wise, it’s very solo-traveler friendly, especially in the historic core. Avoid wandering too far along the river after dark, simply because it gets very quiet.
Stay:
For boutique charm, The Varsity Hotel & Spa* offers modern rooms, a rooftop bar with city views, and spa access, perfect for post-walk relaxation (around €200/night). Chain lovers can check into Hilton Cambridge City Centre, smack in the heart of town and often available for 50,000 Hilton Honors points/night. It’s business-class comfort but right next to the action.
Points & Perks:
If you’ve got British Airways Avios, you can fly into London Stansted or Heathrow and take a quick train. Hilton Gold status (via Amex Platinum) may score you free breakfast at the Hilton Cambridge, a very welcome perk before a day of exploring colleges.
Kraków, Poland – Gothic Romance & Cozy Cafés 🏰☕
Why Go:
Kraków is where medieval Gothic meets café culture. The Old Town is a UNESCO site, wrapped around the largest medieval market square in Europe.
Come September, the summer crowds thin and a soft chill creeps into the evenings, perfect for slipping into a warm café with a slice of szarlotka (apple cake) and a notebook. Between the spires of St. Mary’s Basilica and the looming silhouette of Wawel Castle, you’ll feel that perfect dark academia balance of beauty and mystery.
Offbeat Charm: Beyond the postcard views, explore Kazimierz, the historic Jewish quarter, now filled with vintage shops, indie bars, and art galleries (you nay recogniseit as a set from „Schindler’s list“). Pop into Massolit Books & Café, a bookshop-café hybrid where you could lose hours. For something atmospheric, visit the Collegium Maius, Jagiellonian University’s oldest building (Copernicus studied here), with its arcaded courtyard and scholarly artifacts. And for an autumn walk, the Planty Park, a green belt around the Old Town, is peaceful and leaf-strewn in September.
If you’ve got the stomach for it, a day-trip to Auschwitz concentration camp will introduce you to the horrors of the Holocaust and bring into reality what you learned in history lessons. It’s been years since I’ve been there and I still remember all the emotions I experienced in that place.
Solo Travel Tips:
Kraków is very safe for solo travelers, with plenty of pedestrian zones and a friendly, youthful vibe thanks to its student population. Walking is the best way to explore the Old Town and Kazimierz. Public trams are easy to use if you venture further.
Stay:
For boutique atmosphere, try Hotel Copernicus*, a 5-star housed in a Renaissance building, with exposed beams and an indoor pool under a vaulted brick ceiling (around €200/night off-season). If you’re looking for a chain, Sheraton Grand Kraków offers modern comfort on the Vistula River, often under €180/night or 40,000 Marriott Bonvoy points.
Points & Perks:
LOT Polish Airlines flights can often be booked with Star Alliance miles (transfer from Amex/Chase to United or Air Canada Aeroplan).
Marriott elites get lounge access and late checkout at the Sheraton, great for squeezing in one more morning castle stroll.
Leiden, Netherlands – Dutch Canals & Quiet Academia 🚲📖
Why Go:
Leiden is Amsterdam’s calmer, scholarly cousin, home to the Netherlands’ oldest university, cobblestone alleys, and canals that look especially magical under September’s golden light. With fewer tourists, you can wander in peace past historic almshouses, 17th-century facades, and ivy-covered walls.
Offbeat Charm: Check out the Bibliotheca Thysiana, a perfectly preserved 17th-century library built by a scholar’s will. Visit the Hortus Botanicus, where the university has cultivated plants since 1590 (and where tulip mania began!). For a quirky side trip, explore De Burcht, a circular medieval fortress offering panoramic city views. Evenings are best spent along the canals with a glass of wine, watching bikes whizz by.
Solo Travel Tips:
Leiden is small and extremely walkable/bikeable. It’s a safe, student-filled city, so you’ll blend right in wandering alone. The train station connects directly to Amsterdam Schiphol Airport in under 20 minutes, making it an easy entry or exit point.
Stay:
For boutique coziness, Boutique Hotel d’Oude Morsch* offers stylish rooms in a restored 19th-century military building (around €150/night).
Gor a chain, the Hilton Garden Inn Leiden is reliable and points-friendly, often available for 30,000 Hilton points.
Points & Perks:
Hilton points are the obvious play here. If flying into Schiphol, book award flights using Delta SkyMiles, KLM Flying Blue, or Virgin points, all partners with Amex/Chase and you’ll be sipping coffee by the canal in no time.
Salzburg, Austria – Baroque Beauty & Alpine Backdrops 🎼🍷
Why Go:
Salzburg is like stepping into a period drama, with pastel Baroque buildings, church domes, and the fortress of Hohensalzburg perched above. The birthplace of Mozart and backdrop to The Sound of Music, it’s steeped in both artistic and scholarly heritage.
September brings crisp air and fewer tour buses, letting you enjoy the Old Town at its most atmospheric.
Offbeat Charm: Wander up to the Nonnberg Abbey, the world’s oldest continuously run convent, with views over the city. Visit the St. Peter’s Cemetery and its catacombs carved into the Mönchsberg rock , eerie, beautiful, and blissfully uncrowded. For a cozy evening, duck into Café Bazar, a century-old haunt of writers and artists. If you’re feeling active, take the funicular to the fortress, then hike along the Mönchsberg ridge for sweeping autumn views.
Solo Travel Tips:
Salzburg is compact and easy to explore on foot. Safe, clean, and friendly, it’s perfect for solo wandering. Public buses connect the airport, train station, and outer sights, but you’ll rarely need them in the center.
Stay:
For boutique charm, Hotel Elefant * offers historic elegance in a 13th-century building steps from Mozart’s birthplace (~€160/night).
For chain reliability, the Sheraton Grand Salzburg delivers modern comfort across from Mirabell Gardens, usually around €200/night or 40,000 Marriott points.
Points & Perks:
Flying into Munich and taking a train (about 90 minutes) is often cheaper and bookable with airline miles.
Marriott Bonvoy elites get perks like upgrades and breakfast at the Sheraton, ideal before a day of Alpine exploration.
Travel Q&A:
Plan Your Perfect September Reset Trip 🌍❓
Q: Is September a good time to travel to Europe for a trip like this?
A: Absolutely! September is often considered part of Europe’s shoulder season, meaning you enjoy decent weather and fewer crowds. Kids are back in school, peak tourist numbers drop, and you’ll find that sweet spot of pleasant temperatures (think light jacket or cozy sweater weather) without the sweltering heat. In many of these cities early fall brings beautiful foliage and seasonal events (harvest festivals, cultural events, etc.). Plus, as travel trends show, more people are choosing shoulder season for better value and less stress. So you’re making a savvy move.
Just note: days do get shorter as autumn progresses (especially in northern Europe), so plan your sightseeing accordingly, but a little evening darkness only adds to the dark-academia charm, right?
Q: I have a bunch of credit card points (Amex Membership Rewards, Chase Ultimate Rewards, etc.). How can I use them for this trip?
A: There are so many ways to leverage points and miles here, good on you for saving them up!
For flights, check your Amex or Chase travel portals and transfer partners. For example, Amex MR points can transfer to Avios (British Airways/Aer Lingus), which are great for flights into hubs like London, Dublin, or even for shorter intra-Europe hops (e.g., London to Dublin). Chase UR points transfer to United MileagePlus (fly into Brussels for Ghent, or Munich for Salzburg) and to Flying Blue (Air France/KLM), which can get you to pretty much any major European city via Paris or Amsterdam.
Don’t overlook using points for hotels: Marriott Bonvoy is an Amex and Chase partner, so you could transfer some points to Marriott and cover stays at hotels like the Ghent Marriott with points rather than cash. Hyatt is a Chase partner.
Also, remember the “5th Night Free” perk on Marriott point redemptions: if you book 4 award nights, you get the 5th night free, which can stretch your points further if you decide to linger longer in one spot. Lastly, if you have a travel credit card with broad travel eraser credits (like Capital One Venture or Bank of America Travel Rewards), you can charge things like train tickets, museum passes, or boutique hotels to the card, then wipe those charges with your points.
Bottom line: use points for the big expenses (flights & hotels) and save your cash for the fun stuff (meals, experiences, a vintage book from that cute shop in Dublin…). Your future self, and your wallet, will thank you.
Q: I’ll be traveling solo. How can I stay safe, especially at night?
A: Solo travel in Europe is generally very safe, and all the cities we’ve picked are known for being traveler-friendly and relatively low-crime. Still, it’s wise to follow standard precautions.
Here are some tips: Stay aware of your surroundings: In popular tourist areas, keep an eye on your belongings – pickpockets love distracted sightseers. A crossbody bag or money belt can give you peace of mind. At night: Stick to well-lit, populated areas. Each of these cities has parts that stay lively in the evenings. If somewhere looks deserted or sketchy, trust your gut and maybe grab a taxi or rideshare (Uber operates in many European cities; where it doesn’t, there are local apps or good old licensed taxis). In some larger European cities, the area around the main station may be something of a criminal hotspot. Police are often around in larger numbers, but stay safe especially at night. Some cities have „Nottaxis“ (emergency taxis) that’ll take you home save if you’re stranden somewhere. Look into that if you want to explore at night.
Local customs: Be mindful of local norms, e.g., in Italy, dinner runs late, so walking back to your hotel at 10 or 11 pm is normal and the city will still have people out. In smaller cities like Ghent, things might close earlier, so the streets could be quieter after 9 pm. Nothing unsafe per se, just quieter. If you’re uncomfortable, plan to finish your evening activities by then or join a nightlife tour or hostel event to have some company.
Transport safety: Public transport is usually safe and efficient. Still, late at night, you might opt for a taxi if you’re not near your accommodation. For example, some metro stops around midnight, so if you’re out late, use a taxi or Uber.
Let someone know: As a solo traveler, it’s a good idea to keep a friend or family member in the loop about your general itinerary. Also, consider registering your trip with your country’s embassy or using safety apps like GeoSure for city safety scores in real time. If traveling outside of the EU, I usually register with Elefand, the German foreign office emergency services.
Most importantly, confidence and blending in go a long way. Walk with purpose (even if you’re occasionally consulting Google Maps), and don’t flash valuables. The goal is to look like you know what you’re doing – even if you’re delightfully lost in a medieval alley, no one else needs to know that! 😉
Q: What should I pack for a fall trip to Europe?
A: Great question! Fall weather can vary across Europe, so packing smart will keep you comfy. Here’s a handy checklist: Layers, layers, layers.
Mornings and evenings can be chilly, while afternoons might be mild. Pack a mix of t-shirts or light long-sleeves, a couple of sweaters, and a medium-weight jacket. A stylish trench or a packable down jacket can be a lifesaver on cooler days and elevates the dark academia look. 🎩
Comfortable walking shoes: You’ll be logging steps on cobblestones and uneven streets. Bring at least one pair of broken-in shoes (ankle boots or sneakers) with good support. Maybe also a nicer pair of boots or oxfords for evenings out (still comfy, though your feet will thank you).
Travel umbrella or rain jacket: A compact umbrella is gold. September can surprise you with a rain shower, especially in the UK, Belgium, or Ireland. Many European cities have sudden drizzles. Alternatively, a lightweight waterproof jacket with a hood works too.
Scarf and accessories: Not only can a scarf keep you warm on a brisk morning, but it also adds a dash of European flair to your outfit. In true dark academia spirit, perhaps a plaid or neutral-tone scarf. Throw in some gloves and a beanie if your itinerary skews late fall or you’re headed to northern areas.
Day bag: A secure backpack or crossbody bag to carry your daily essentials (camera, guidebook, water bottle, snacks acquired from that cute market). Go for something that closes securely (zippers) to deter pickpockets. Keep valuables close to your body and mind your phone.
Power adapter: Europe’s plugs differ (mostly Type C “Europlug” on the continent, Type G in the UK). Bring a universal adapter and remember voltage is higher (220-240V), so check your electronics or bring a converter if needed (most phone/laptop chargers are dual voltage, though).
Travel journal or Kindle: You’ll have inspiring moments, maybe jot them in a notebook while sitting in a Parisian-esque cafe in Ghent, or load up some classics on a Kindle for train rides.
Medications & small first aid: Include any personal meds, plus some basics like ibuprofen, band-aids (for any blister from walking), and perhaps motion sickness pills if you plan boat rides.
Copies of documents: Keep digital/paper copies of your passport, credit card info, and itinerary separately, just in case.
And a reminder: ensure your passport is valid for at least 6 months beyond your trip. Pack versatile pieces that you can re-wear, many European hotels have laundry service (pricey) but also look for self-service laundromats if needed (like Washeteria in Dublin). Ultimately, pack what makes you feel comfortable and confident, you’ll likely pick up a souvenir sweater or two along the way, so leave a little room in your suitcase!
Q: Should I plan to visit all 5–7 cities on one trip, or is it better to pick just a few?
A: While the overachiever in all of us might be tempted to “collect ’em all,” I’d recommend quality over quantity for a mental reset trip. Each of these cities has its own allure and deserves a few days to soak in. If you have a whole month (lucky you!), you could feasibly string together 5–7 cities at a comfortable pace, perhaps spending 3-4 nights in each and using Europe’s excellent train network or short flights to hop between countries. However, most people with limited vacation time might aim for, say, ~2 weeks. In that case, choose 3 or 4 cities that excite you most and are logistically sensible together.
For example: UK & Ireland focus: Camebridge → Dublin (a nice northward progression, flights or train/ferry combos connect them).
Central Europe focus: Ghent → Leiden→ Salzburg (with maybe a Paris or Brussels stop in between for transit).
Mix & match: Dublin→ Camebridge→ Ghent (start cool up north, explore the Euroexpress).
Consider travel times: you don’t want to spend half your trip in transit. Group cities by proximity to minimize long hauls. Also factor in your travel style, do you enjoy rapid pace or slow travel? A mental reset might mean not rushing. It can be incredibly rewarding to linger longer in one spot, become a temporary regular at a café, and really absorb the atmosphere. Maybe you fall in love with Ghent and decide to day-trip to Bruges and Antwerp from there instead of packing up again – go for it!
And for us corporate workers, a long weekend in one city might be the way to go.
Flexibility is the solo traveler’s superpower. A sample 2-week itinerary might be: Krakow(4 nights) – train to Salzburg(3 nights) – fly to Dublin (4 nights) – quick hop to Camebridge/London (3 nights).
Ultimately, plan around what sparks joy for you, and leave a little wiggle room for serendipity. Remember, you can always return for the cities you skip, Europe’s not going anywhere, and having a reason to come back is the best souvenir. 😉
Conclusion – Embrace Your Fall Adventure & Find Your Inspiration 🍂✈️
September in Europe offers the perfect canvas for your mental reset. As you wander through Camebridge ’s quads or Ghent’s lantern-lit lanes, don’t be surprised if you feel a lightness you haven’t in a while. It’s amazing how a change of scenery, especially one with old bookstores and cozy coffee shops , can remind you of the simple joys beyond the 9-to-5 grind.
Each city on this list isn’t just a destination, but a gentle invitation to slow down and savor life: whether that’s journaling under a Gothic archway, people-watching from a café with a frothy cappuccino, or striking up a conversation with a friendly stranger at a pub. You’ll return home with your mind refreshed, creativity rekindled, and maybe a few new anecdotes to spice up those Monday morning meetings (just wait till they hear about the time you got lost in a medieval library at night!).
Feeling motivated and excited yet? The fall winds are changing, and your European adventure is calling. Go ahead, take that “Europe mental reset trip”, invest in yourself, and step into the pages of the story you’ve been dreaming to tell. We’re here cheering you on every step of the way! 🙌
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Got questions or want to share your own travel plans? Drop a comment below or reach out. I love hearing from fellow adventurers. Here’s to making this September your most transformative travel experience yet. Sláinte, Prost, Cheers! 🥂 Safe travels and happy reset!
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I stepped off the train, briefcase in hand, and felt like I’d wandered onto a film set. It was a misty September evening, and the cobblestones of Old Town Edinburgh glistened under gaslight. In that moment after a long week of meetings, I wasn’t a consultant on a work trip, I was the main character in a classic European romance.
If you’re a 30-something professional dreaming of living out your own movie scene (without burning all your vacation days), keep reading.
September in Europe is prime time for romantic city escapes: the summer crowds have thinned, the weather is mellow, and the old-world streets beckon for you to write your own story.
From popular classics to offbeat gems with a dark academia twist, here are five inspiring city escapes, complete with itineraries, solo-friendly tips, and a dash of personal brand of sass to turn your next work trip extension into a cinematic adventure.
Oxford’s dreamy spires and golden-stone colleges feel straight out of a period drama. Wander the quads at twilight and you might hear the echoes of scholars and poets past.
Why Go
Oxford is practically the blueprint for a “dark academia” romance and feeling like you’re on a movie set. Its 12th-century university colleges, ivy-clad courtyards, and grand libraries (hello, Bodleian Library) exude old-world charm. Walking under the gaslit arches of Magdalen College cloisters on a foggy morning or evening, you’ll feel like you’ve fallen into a Tolkien novel or a Harry Potter film. And indeed, parts of Harry Potter were filmed at Christ Church College.
September finds Oxford calm but alive: summer tourists have left, students trickle back for Michaelmas term, and the early autumn light makes those honey-colored buildings glow. It’s the perfect time to stroll hand-in-hand (even if solo, you can romantically hold your coffee) through historic lanes and along the River Thames (called the Isis here).
5-Day Itinerary Highlights
(Feel free to mix work and play – Oxford is compact, so you can sightsee in small doses between emails.)
Day 1: Old Town & University Tour
Start at the Radcliffe Camera, Oxford’s iconic round library, then join an official walking tour by the city’s tourism board. An expert guide (often an Oxford alum) will lead you through hidden passageways and college quads, sharing witty insider tales. You’ll see the Bodleian Library, Bridge of Sighs, and peek into colleges like New College or Christ Church (Hello Hogwarts). Afterwards, unwind at The Eagle and Child pub, once the meeting spot of Tolkien and C.S. Lewis, for a pint of ale and serious literary vibes.
Day 2: Literary Landmarks & Leisure
Spend your morning at Blackwell’s Bookshop, an Oxford institution with an underground chamber that will delight any booklover. Then visit Christ Church Meadow for a peaceful stroll by the Cherwell River; if it’s a warm afternoon, go punting (propel a flat boat with a pole) for a classic Oxford romance moment. In the evening, catch a Shakespeare play or classical concert at the 12th-century University Church of St. Mary, culture here is as thick as the ivy on the walls.
Day 3: Museums & Markets
Explore the Ashmolean Museum (ideally directly across from your hotel). It’s the world’s oldest public museum, full of art and antiquities. Don’t miss the rooftop cafe for lunch with a view.
In the afternoon, browse the Covered Market (since 1774) for local chocolates, Oxford University merch, and fresh pastries. As dusk falls, climb the St. Mary’s Church Tower for a panoramic sunset over those “dreaming spires.” It’s pure movie magic as the bells toll.
Day 4: Cotswolds Day Trip
Take a morning off from city life and hop a train or bus to nearby Cotswold villages (such as Bibury or Stow-on-the-Wold). These storybook towns of thatched cottages and blooming gardens will make you feel like Elizabeth Bennet searching for Mr. Darcy. It’s an easy solo excursion and a great way to unwind. Be back in Oxford by evening for a cozy dinner at a local bistro (try Georges Street Social or Quod for modern British fare).
Day 5: College Gardens & Farewell Tea
On your last day, soak up any colleges or museums you missed. Magdalen College’s deer park and Addison’s Walk are wonderfully tranquil in the morning. For a grand finale, indulge in afternoon tea at the Randolph Hotel or The Old Parsonage, delicate sandwiches, scones, and a pot of Earl Grey to toast your Oxford adventure.
With your bags packed, take one last twilight stroll along Broad Street as streetlamps flicker on. It’s a scene straight from a novel – and you lived it.
Solo & Logistics
Oxford is very solo-traveler friendly and safe, with low crime rates and a student town vibe. (Just mind the cyclists whizzing by on narrow lanes!) The city is a quick 1-hour train from London (trains from Paddington or Marylebone). Use a Contactless card or Oyster on Great Western Rail or Chiltern Railways for easy payment, or snag advance tickets for cheaper fares.
Once in Oxford, everything in the center is walkable; no car needed. If you want to explore further (like Blenheim Palace or Cotswolds villages), buses and guided tours abound.
Where to Stay
For a true “posh academia” experience, stay at The Randolph * Hotel, Graduate Oxford (Hilton) – a historic five-star right in the heart of the city. It’s across from the Ashmolean and steps from the colleges, so location is unbeatable. Couples especially love it here, rating the location 9.6/10 for two-person trips. The decor is all Alice-in-Wonderland whimsy (a nod to Oxford’s literary heritage) and you can earn or use Hilton Honors points since it’s part of Hilton’s Curio Collection.
If you have Marriott Bonvoy points instead, the Courtyard by Marriott* Oxford City Centre is a solid option, modern amenities, a rooftop terrace, and just a short stroll from Oxford Castle.
Pro tip: Using points for your hotel can save your cash for more bookstore splurges. No judgment.
For boutique lovers, try Old Bank * Hotel or Malmaison* Oxford, a former Victorian prison turned chic hotel, for a unique stay.
Bleisure Perks: Need to squeeze in work? Oxford has you covered. Many cafes offer free Wi-Fi, sip a flat white at Vaults & Garden café (in a church crypt by the Radcliffe Camera) while catching up on emails.
The city’s peaceful parks (University Parks or Christchurch Meadows) are perfect for walking “meetings” with yourself to brainstorm that next big project idea. By night, unwind with a ghost tour or a literary pub crawl, after all, all work and no play makes Jack a dull boy, as one famous Oxford alum wrote (looking at you, Mr. King).
In Oxford, you’ll find inspiration around every medieval corner.
Edinburgh, Scotland – Gothic Romance Meets Modern Buzz
Edinburgh Castle crowns the city, its ramparts and turrets evoking scenes from a historic drama. In September’s golden light, Edinburgh feels like a living movie set, part medieval epic, part cozy romance.
Why Go
With its brooding Edinburgh Castle perched atop Castle Rock and an Old Town of medieval closes and spires, Edinburgh oozes cinematic atmosphere. J.K. Rowling famously wrote Harry Potter in its cafés, and the city itself feels like a magical realism novel come to life. The architecture is Gothic and grand, the history is palpable, and come September, the summer frenzy (August’s Festival crowds) has faded, leaving a creative, calm energy in the crisp air.
Strolling down the Royal Mile or through Georgian New Town in early autumn, you might catch the scent of fireplace smoke mixed with roasting coffee – talk about mood setting! Edinburgh combines romance and “dark academia” vibes (old libraries, universities) with the comforts of a modern capital. It’s also extremely safe and welcoming; in fact, central Edinburgh is considered very safe, even for solo travelers.
6-Day Itinerary Highlights
(Ideal for a long weekend plus a few remote-work days. If you can spare a full week, even better. Edinburgh will fill it easily.)
Day 1: Royal Mile & Castle
Start at the top: Edinburgh Castle. Aim for opening time to beat crowds and tour this iconic fortress, seeing the Scottish Crown Jewels and views clear to the sea. As you exit, you’re at the head of the Royal Mile – the medieval street linking castle to palace. Meander downhill through cobbled alleys (called “closes”), past street performers and bagpipers. Pop into St. Giles’ Cathedral for stunning stained glass and into Gladstone’s Land, a 17th-century tenement house museum, to time-travel. Grab lunch at Deacon Brodie’s Tavern (named for the real Jekyll & Hyde inspiration). By late afternoon, reach Holyrood Palace, the Royal’s residence in Scotland, at the foot of the Royal Mile. Tour the stately rooms and the abbey ruins in the garden.
Evening plan: ascend Calton Hill (short climb) for sunset city panoramas, then treat yourself to a whisky tasting at a cozy pub on Rose Street in New Town. Slàinte!
Day 2: Dark Academia & Ghosts
Dive into Edinburgh’s scholarly side at the National Museum of Scotland (don’t miss Dolly the sheep, the world’s first cloned mammal,science magic!). Then swing by the University of Edinburgh campus; the Old College and gorgeous Talbot Rice Gallery will satisfy your academic aesthetic cravings. Afterwards, channel your inner bookworm at The Elephant House cafe, where J.K. Rowling wrote parts of Harry Potter or the Old Town’s Central Library (a beautiful Carnegie library).
As night falls, embrace the city’s eerie romance with a ghost tour under the South Bridge vaults or in Greyfriars Kirkyard (I recommend fhe Double Dead Tour). It’s spooky, it’s fun, and it’ll give you chills – the good kind.
End the night with live folk music at Sandy Bell’s pub, you’ll feel like you’re in a jaunty pub scene from a film.
Day 3: Highlands Day Trip
One of the best parts of Edinburgh is how quickly you can escape to the dramatic Scottish Highlands.
Rent a car for a day tour to the Highlands or Loch Ness, many depart around 8am. You’ll journey through misty glens, see rainbows arching over lochs and maybe visit Glencoe (site of Skyfall’s filming for Bond fans) or quaint Pitlochry.
Breathe that fresh mountain air, it’s a refreshing break from city life and unbelievably scenic. Back in town by evening, reward yourself with a hearty meal of haggis, neeps & tatties ( if you dare) at The Devil’s Advocate or a trendy spot in the Grassmarket area.
Day 4: Arthur’s Seat & Tea Time
Start with a sunrise hike up Arthur’s Seat, the extinct volcano in Holyrood Park. It’s an energizing walk (about 30-45 minutes up) and the 360° views of Edinburgh’s spires, sea, and hills are worth every step. A true main-character moment as the wind tousles your hair at the summit. After descending, enjoy a well-earned afternoon tea at The Balmoral Hotel or Signet Library’s Colonnades for ultra elegance. Finger sandwiches and scones taste even better beneath grand chandeliers.
Spend the afternoon wandering Princes Street Gardens beneath the castle or shopping for tartan souvenirs in smaller streets. If work calls, duck into the Edinburgh Central Library or a café with Wi-Fi in New Town, like The Milkman or Thomas J. Walls coffee. By now, you’ve earned a relaxed evening , maybe a film at the vintage Cameo Cinema or simply a stroll through Dean Village, a storybook-worthy hamlet by the Water of Leith.
Day 5: New Town & Culture
Explore Edinburgh’s Georgian New Town: its broad streets and elegant crescents (designed in the 1700s) are a UNESCO World Heritage site. Visit the Scottish National Gallery on Princes Street for a dose of art (free entry). Stroll up to George Street for high-end shops and chic lunch spots, try The Ivy on the Square or Dishoom for an unforgettable meal. In the afternoon, check out Stockbridge, a leafy neighborhood full of indie boutiques, and if it’s Sunday, a fantastic street market. Catch golden hour on Circus Lane (most Instagrammable mews street ever).
End your day with a literary pub tour or an underground vaults history tour, a little learning with your libation.
Day 6: Wrap-Up or Add-On
If you’re extending the work trip, use today for catch-up (the city has plenty of coworking spaces if you need them, like Cowork at CodeBase). Otherwise, consider a quick train trip to Glasgow (50 min away) for a contrasting dose of urban cool, or visit nearby Rosslyn Chapel (yes, Da Vinci Code fans, that one) to satisfy any remaining quest for mystery. Come evening, climb the Scott Monument if you dare (narrow stairs but great view), then toast farewell with a gourmet dinner at The Witchery by the Castle. Dining by candlelight in a 16th century merchant’s house, you’ll feel like an actor in a lavish period piece, ending your Edinburgh story on a truly romantic note.
Solo & Logistics
Edinburgh is incredibly welcoming to solo travelers, expect friendly locals and a lively international scene. The central areas (Old Town, New Town, Stockbridge) are very safe. I never once felt unsafe, even late at night.
Public transport is straightforward: take the Airlink 100 bus or Tram from the airport to city center (both run frequently, ~30 minutes). Within town, you can walk almost everywhere. Buses and trams cover the rest; get a Ridacard or use contactless for easy tap-and-go rides. If you plan on heavy sightseeing, consider the Royal Edinburgh Ticket, which gives 48-hour unlimited hop-on-hop-off bus access plus entry to Edinburgh Castle, Holyrood Palace, and Royal Yacht Britannia, a great bundle for first-timers.
The newer Edinburgh City Pass is another option, covering multiple attractions and even day tours. However, nothing beats simply wandering the streets here, the city is the attraction.
Pack layers. September can bring sun, wind, and a wee bit of rain in one day and comfortable shoes for those hills.
Where to Stay
For bleisure travelers, Edinburgh has plenty of options. If you’ve got Hilton Honors points, the Waldorf Astoria Edinburgh – The Caledonian (recently rebranded to Hilton’s Curio Collection) is a top pick – a historic former rail hotel right at Princes Street. Standard reward nights can be found for roughly 54,000–95,000 points, which is a steal for its luxury (plus castle-view rooms!).
Marriott loyalists will love The Glasshouse*, Autograph Collection – a 5★ boutique hotel built into a 172-year-old church façade, complete with a rooftop garden overlooking Calton Hill.
Coming with a partner? The new Market Street Hotel*, a design-forward boutique or The Balmoral (Edinburgh’s grand dame) scream romance.
And heads up, Hyatt fans: Edinburgh welcomed the W Edinburgh in late 2023 (Marriott Bonvoy, actually) and is slated for a Hyatt Centric at Haymarket soon, so you’ll have even more choices to earn points on your stay.
Wherever you sleep, try to stay central (Old or New Town) so you can walk to most sights; areas like the Royal Mile, Princes Street, or Grassmarket are ideal and safe even at night.
Pro tip: Use those hotel points to upgrade to a castle-view room or exec lounge access , sipping champagne with Edinburgh Castle in sight is a memory you won’t forget.
Bleisure Perks: Edinburgh understands the work-play juggle. Many hotels here cater to professionals with business centers and speedy Wi-Fi. The Hilton Edinburgh Carlton even has an executive lounge if you need a quiet space. If you need a midday desk, check out The Quartermile area’s coffee shops (with many remote workers tapping away). And when the laptop closes, reward yourself: maybe with a jog up Calton Hill or along the Water of Leith walkway ,much more fun than the hotel gym. The city’s compact nature means you can be on a Zoom call at 4 PM and watching traditional Scottish dancing at a ceilidh by 7 PM. That’s the work-life balance we’re after!
Prague’s Old Town at dusk feels like a stage set: lantern-lit lanes, Gothic towers, and the Vltava River reflecting the city lights. It’s easy to imagine Mozart or a film noir spy strolling beside you in this romantic, mysterious city.
Why Go
Prague is the quintessential “feel like you’re in a movie” city. Its medieval Old Town and Charles Bridge have graced countless films with their storybook looks, and the city’s blend of Baroque opulence and shadowy gothic corners nails that romantic yet mysterious vibe. As one travel writer put it, “Prague has an eerie beauty that makes it perfect for those who love a little mystery”. This is a place where you can waltz in an Old World ballroom one night and seek out alchemists’ alleys the next.
September in Prague is magical: summer’s heat and crowds subside, the weather is comfortably mild – think light jacket in evenings and you might catch early autumn festivals like the St. Wenceslas wine festival or harvest markets. The city’s parks start turning gold and the outdoor cafes are still open, the perfect backdrop for a solo traveler sipping mulled wine on a balmy evening, feeling like the star of a European art film.
5-Day Itinerary Highlights
Day 1: Old Town Charm
Begin in Staroměstské náměstí (Old Town Square) under the gaze of the Astronomical Clock. At the strike of the hour, watch the clock’s little mechanical saints dance , it’s kitschy and wonderful. Wander the maze of cobbled lanes, discovering hidden courtyards and the baroque Klementinum libraries.
For a movie moment, climb the Old Town Hall Tower for a panoramic view of Prague’s red rooftops and church spires. By late afternoon, cross Charles Bridge when the light is golden. Street musicians play classical melodies as swans drift on the Vltava below. Yes, it’s as romantic as it sounds.
On the Little Quarter side, ascend to Prague Castle by twilight. St. Vitus Cathedral’s stained glass will glow in the low sun, and from the castle ramparts you can see the whole city fade into dusk. Have dinner in Malá Strana (Lesser Town) at a traditional Czech tavern (try roast duck with dumplings and cabbage) and raise a pint of Czech pilsner. Na zdraví!
Day 2: Castle District & Gardens
Dive deeper into Prague Castle in the morning: tour the Old Royal Palace, St. George’s Basilica, and Golden Lane, where medieval castle artisans and legend says, alchemists – once lived. Your Prague CoolPass or city pass can cover these, saving time and cash. Next, wander the Royal Gardens and let yourself daydream on a bench facing the Belvedere palace, it’s a serene spot to journal or catch up on work reading. After lunch, visit the Strahov Monastery Library, a baroque hall so stunning it looks straight out of Beauty and the Beast (ceiling frescoes and floor-to-ceiling old books, heart eyes!). Reward your eyes and taste buds with a beer at the monastery brewery nearby.
By late afternoon, head to Petřín Hill: ride the funicular up and climb the mini-Eiffel Tower for sweeping city vistas. As evening falls, find a riverside spot (perhaps on Štřelecký Island) to watch the city lights twinkle on the water. Romantic, check.
Day 3: Bohemian Culture & Cafés
Start with a dose of art at the Alfons Mucha Museum (Art Nouveau posters = Prague’s soul) or the National Gallery. Then indulge in Prague’s grand café culture: have coffee and cake at Café Louvre or Café Savoy, where writers like Kafka once pondered. In the afternoon, cross the quirky Dancing House (take a photo of this modern “Fred & Ginger” building amid Prague’s old skyline) and explore New Town around Wenceslas Square. This area has more contemporary local life and great shopping if you need a break from the past. Come evening, treat yourself to a classical concert in a palace. Many historic venues like Municipal House or Mirror Chapel at Klementinum host nightly concerts (often Vivaldi’s Four Seasons or Mozart pieces – fitting, as Mozart premiered Don Giovanni in Prague). Hearing live classical music in a gilded hall will make your heart swell, a scene right out of a period film. After the show, take a midnight stroll across an almost-empty Charles Bridge for peak main-character energy.
Day 4: Offbeat Adventures
Hop on a morning train (or organized tour) to Český Krumlov, a UNESCO-listed fairy-tale town about 2.5 hours away. Its tiny lanes, pastel Renaissance homes, and hilltop castle over a bend in the river feel like a movie set, because they have been (see: The Illusionist)! If you’re short on time, alternatively do Kutná Hora (1h by train) to see the famous Bone Church (hauntingly beautiful) and medieval silver mines, very Dan Brown vibe.
Back in Prague by evening, explore the hip Vinohrady neighborhood. Grab dinner at a local bistro (this area has great international cuisine and wine bars). If you’re up for nightlife, the city’s jazz clubs are legendary. Check out Jazz Dock on the river or Reduta Jazz Club for soulful tunes that transport you to a smoky 1940s café scene.
Day 5: Markets & River Cruise
Spend your final day leisurely. In the morning, browse Havelské Tržiště market for souvenirs (handmade puppets, anyone?). Then perhaps hit any remaining museums , the Museum of Communism offers a fascinating (and sobering) look at Prague’s more recent history. In the afternoon, do as any romantic would: take a Vltava river cruise. A one-hour panoramic cruise or an evening dinner cruise lets you glide under the Charles Bridge and around Prague’s islands, with multilingual commentary narrating the sights. It’s touristy, sure, but floating past illuminated Prague Castle with a drink in hand is unforgettable.
For your finale, ascend to Letná Park’s beer garden. As you sip a beer under chestnut trees, you’ll see Prague’s entire Old Town spread below, bridges crossing the river like ribbons. Sunset here is pure poetry the perfect end to your Prague story.
Solo & Logistics
Prague is consistently ranked among Europe’s safest destinations for solo travelers. Violent crime is rare; just watch for pickpockets in touristy areas like Charles Bridge or trams (common sense stuff). English is widely spoken in hotels and restaurants, and any language barriers can usually be overcome with a smile and maybe a pointed finger at the menu. The city is very walkable in the historic center, though bring comfy shoes because those cobbles can punish your feet.
Public transport is excellent: metro, trams, and buses cover everywhere – pick up a 24-hour or 72-hour transit pass (120 CZK for a day, 330 CZK for 3 days) for unlimited rides, including to/from the airport. A funicular takes you up Petřín Hill, and yes, Uber works in Prague too for late nights. Consider getting the Prague Visitor Pass or Prague CoolPass (formerly Prague Card) if you’re hitting many paid attractions; it includes public transport and entry to 80+ sights. For example, the official Prague City Pass with transport can be booked for 2-5 days, convenient for seeing major sites like Prague Castle without buying separate tickets.
One more tip: Prague’s currency is the Czech Crown, not euro – you’ll get roughly 22-24 CZK to 1 USD. Use ATMs or contactless payments to avoid the notorious currency exchange rip-offs in tourist centers.
Where to Stay
Prague offers everything from centuries-old palaces to modern design hotels. For a splurge (and to use those hard-earned Marriott Bonvoy points), check out Augustine*, a Luxury Collection Hotel, Prague, a former monastery turned 5★ retreat. It’s Marriott Category 6 (around 50,000 points per night), and staying in its elegant cloisters with a view of Prague Castle will make you feel like royalty. Another luxe pick is Hotel Paris Prague (an art-nouveau gem) or Four Seasons Prague, but those are better for splashing cash unless you have their points.
On the boutique side, consider Golden Well* (U Zlaté Studně), a romantic hideaway right beneath the Castle, often rated among the most romantic hotels in the world.
For Hyatt fans, Prague recently welcomed the Andaz Prague* in the Sugar Palace – Hyatt’s first in the country. The Andaz blends modern luxury with heritage details (think marble staircase, art inspired by Czech legends). It’s a great use of World of Hyatt points, and its location on Senovážné Square is walking distance to Old Town.
If you prefer the Hilton family, Hilton Prague Old Town is solid and centrally located, or the big Hilton Prague across the river for executive perks (though its architecture is more communist-era than fairytale).
Mid-range travelers will find plenty of options too: MOODs* Charles Bridge or Hotel Pod Věží* are charming and won’t break the bank. And if you love a rooftop view, Hotel U Prince has a famous rooftop bar right on Old Town Square.
Affiliate note: Many Prague hotels can be snagged via Booking.com – often with free cancellation – so you can lock in a great deal while keeping plans flexible.
Bleisure Perks: Prague is an increasingly popular “digital nomad” hub, meaning you’ll find coworking spaces (check out Impact Hub or Locus Workspace) and cafés with Wi-Fi on nearly every block (try Café Lounge or Muj Šálek Kávy for good coffee + outlets).
Need to impress a client or partner? Schedule a meeting at Café Imperial, its mosaic ceiling and Art Deco glam will set the stage nicely. After work, reward yourself with a spa afternoon. Czech beer spas are a thing where you soak in a tub of warm beer and hops (with unlimited beer to drink). It’s quirky but surprisingly relaxing!
And don’t forget to leverage your airline miles for this trip: if you’re coming from within Europe, consider using Miles & More on Lufthansa or its partners to fly into Prague (they often have availability into PRG). From North America, transferring your Amex Membership Rewards to Iberia Avios can nab you an off-peak business class seat for as low as 34,000 points, an incredible sweet spot to arrive in style.
However you get here, Prague will welcome you with open arms, a dumpling-filled dinner, and likely a Pilsner or two. Work hard, play hard, and leave with your heart full of Bohemian rhapsodies.
Heidelberg, Germany – Romantic Academia on the River
Heidelberg is the city of Goethe’s poems and Student Prince legends. Come September, morning mist hugs the Neckar River and castle ruins, making you feel like you’ve wandered into a 19th-century painting.
Why Go
Heidelberg is the definition of romantic understatement. Nestled in a lush valley along the Neckar River, it’s a smaller city that has inspired writers, philosophers, and painters for centuries. If Oxford and Prague have dark academia vibes, Heidelberg is their sentimental German cousin: home to Germany’s oldest university (since 1386) and a storybook baroque Old Town untouched by WWII.
Stroll the Philosopher’s Way (Philosophenweg) overlooking the city and you’ll see why thinkers like Mark Twain lingered here. Heidelberg’s half-ruined sandstone castle on the hill, the old bridge with its two towers, the cobblestone lanes… It all feels like a set for a period romance or perhaps a sepia-toned film about youthful scholars in love. The German concept of Sehnsucht (longing) might as well have been coined in Heidelberg. In September, the summer tourists are mostly gone, the weather is gentle (great for hiking and outdoor cafes), and the hills start to show the first autumn colors. It’s ideal for a relaxed escape where you can mix intellectual sightseeing with lazy, romantic downtime.
5-Day Itinerary Highlights
Heidelberg is great for slow travel – you won’t rush here. Perfect if you’re juggling some remote work; you can leisurely sightsee in chunks.
Day 1: Altstadt Ambling
Get acquainted with Heidelberg’s Altstadt (Old Town). Wander down Hauptstraße, one of Europe’s longest pedestrian streets, lined with boutiques, gelato shops, and students on bikes. Explore Marktplatz, with the Town Hall and Holy Spirit Church. Maybe climb the church tower for a view. For lunch, grab a bratwurst or pretzel from a street stall (when in Germany!).
In the afternoon, tour the Heidelberg University campus: peek into the Old University Assembly Hall and definitely visit the Studentenkarzer (Student Prison), a quirky little “jail” where rowdy 19th-century students were locked up for dueling or pranks, leaving behind graffiti on the walls. It’s oddly fascinating and very dark academia!
By early evening, cross the Old Bridge (Alte Brücke) with its medieval gate and statue of a monkey (a fun photo op) to the Philosopher’s Way on the opposite bank. A short, mildly steep walk up yields panoramic views of the city, river, and castle – pure romance, especially at sunset when the red roofs glow. Sit on a bench where poets once pondered life’s questions, and feel your mind clear of any work stress. Dinner in a traditional tavern, try Zum Seppl or Schnitzelbank for local flavor (and flavors!).
Day 2: Castle & Culture
Heidelberg Castle time! Take the historic funicular (or hike, if you’re up for it) to the castle grounds. The ruins are evocative and photogenic, and the terrace view over town is divine. Check out the massive wine barrel in the cellar and the German Apothecary Museum inside, quirky highlights that bring history to life. Your HeidelbergCARD tourist pass likely covers the funicular and castle entry, so use it. After pretending you’re a forlorn princess in the castle gardens, head back down for a museum or two: the Palatinate Museum (Kurpfälzisches Museum) in town offers art and archaeology, while Heidelberg University’s Library and Museum give insight into academic heritage. If you have an academic bent, the University Library’s main hall is gorgeous, dark wood and stained glass, very Hogwartsian. Later, treat yourself to Kaffee und Kuchen (coffee and cake) at Café Gundel or Schmelzpunkt (their cheesecake is heavenly). In the evening, join the locals on the Neckarwiese, a grassy riverbank park, for a relaxing stroll. Often, student bands or buskers play music here. Wrap up with a riverside dinner at Wirtshaus zum Nepomuk by the Old Bridge, where candlelight and river sounds set a romantic scene.
Day 3: Philosophers & Vineyards
If today’s a work day for you, start early with a focused session, the serene atmosphere here can actually boost productivity!
Then reward yourself in the afternoon with something different: perhaps a boat cruise on the Neckar. There’s a lovely excursion upstream to Neckarsteinach, known as the “Four Castles” tour. You’ll glide past wooded hills and storybook fortresses, a peak romantic movie scenery. Back in Heidelberg, delve into the Philosopher’s Way properly, not just the viewpoint, but follow the path through terraced vineyards and orchards. There are descriptive signs quoting famous thinkers who walked there. It’s peaceful and green, with spots to sit and read or sketch.
If you brought your partner along, this walk is incredibly romantic; if solo, it’s wonderfully reflective. For a low-key evening, catch a film at the Karlstorkino (arthouse cinema) or see if there’s an outdoor film screening or university event. Being a university town, there’s always something happening. Alternatively, join a wine tasting at a local winery or wine bar. The surrounding Rhine-Neckar region produces lovely white wines (Riesling!) and what better place to clink glasses than a 300-year-old wine cellar?
Day 4: Day Trip to the Black Forest or Strasbourg
Heidelberg’s location makes it tempting to venture further afield for a day. Hop on a morning train to Baden-Baden (about 1 hour) to soak in thermal spas and stroll a posh 19th-century resort town on the edge of the Black Forest, talk about old-world movie glamour! Or take a 1.5-hour train to Strasbourg, France, to add an international twist. Have French pastries for breakfast and German sausages for lunch on the same day. If you prefer to stay in-country, nearby Speyer (30 min drive/train) has an impressive cathedral and a surprisingly cool Technology Museum with planes and space shuttles. Whichever you choose, you’ll be back by dinner. Treat yourself to Schnitzel or Flammkuchen (tarte flambée) and swap day-trip stories with fellow travelers at a communal beer table. Heidelberg’s friendly vibe makes it easy to chat.
Day 5: Heidelberg’s Heart
Spend your last day savoring Heidelberg itself. Browse the Handschuhsheim farmers’ market in the morning (if it’s open; often Wednesdays or Saturdays) to feel like a local picking up fresh bread and flowers. Climb (or bus) to Heiligenberg on the north side, the hill opposite the castle, to explore the eerie Thingstätte (an amphitheater from the 1930s) and the ruins of an ancient monastery. It’s a bit offbeat and usually quiet, with birdsong and forest all around. Later, indulge in a final shopping stroll on Hauptstraße, maybe pick up a Heidelberg print or some Studentenkuss chocolates (cute locally made chocolates named “Student’s Kiss” – perfect souvenir!).
As twilight falls, consider a riverfront dinner cruise or simply park yourself on the Old Bridge as the city’s lights blink on. When the castle is illuminated at night, reflecting in the river, it’s straight-up romantic movie material. Feel that contented sigh escape your lips? That’s Heidelberg working its magic on you.
Solo & Logistics
Heidelberg is a small city and extremely safe and easy to navigate. Many residents speak English (it’s a university town with lots of international students) and the vibe is relaxed. Walking is the best way to get around Old Town and the university area. To cover longer distances, Heidelberg has an efficient bus and tram network – your HeidelbergCARD includes free public transport within the city. If arriving by air, the nearest big airport is Frankfurt (FRA); from there it’s a 50-minute direct train or shuttle ride to Heidelberg, which makes it popular for quick getaways. Trains are frequent, but do book in advance for cheaper fares on the ICE fast trains. Once in town, no car needed – in fact, the Altstadt is car-free in many parts. September brings mild weather (highs ~20°C/68°F), though have an umbrella handy for the occasional rain shower. Crowds are lighter than summer, but it’s still wise to visit the castle early in the day. The tourist card (HeidelbergCARD) is worth it for a 2-4 day stay, it bundles the castle ticket (with funicular ride) and free local transit, plus discounts at museums and even some restaurants. Pick it up at the train station or online.
And while you’re unlikely to get lost in Heidelberg, if you wander off the beaten path, just look for the spire of the Holy Spirit Church or the castle on the hill to reorient, both are visible from almost anywhere.
Where to Stay
Heidelberg offers cozy romance at every budget. If you have a stash of Hilton Honors points, you’re in luck – the Hilton Heidelberg opened recently in the city center, bringing American-style comfort with a touch of German flair. It’s right by the Neckar riverfront and just 1 km from Old Town, so you can walk to most attractions. The hotel has an executive lounge and even an airport shuttle, catering perfectly to bleisure travelers. Points nights start around 40,000–60,000 points depending on season (and you’ll earn points for that spa treatment you deserve).
For Marriott members, pickings in Heidelberg proper are slimmer, but the Heidelberg Marriott Hotel is a short bus ride from Old Town , it’s along the river with lovely views and you can use/earn Bonvoy points there.
A really atmospheric choice (non-chain) is Hotel Zum Ritter St. Georg,* a Renaissance building from 1592 smack in the middle of Old Town – talk about sleeping in history.
Boutique hotel fans will love Arthotel* Heidelberg (modern chic inside a historic facade) or Hotel Villa Marstall* (an intimate hotel in a 19th-century villa by the river).
As always, check Booking.com for deals, sometimes you’ll find a steal for a 4★ hotel with breakfast included, especially mid-week when business traveler traffic is lower.
Fun fact: Many Heidelberg hotels offer free transit passes for guests during their stay. Ask at check-in, it’s a common local perk so you might not even need to buy tickets while you’re here.
Bleisure Perks: Heidelberg may not be a buzzing metropolis, but that’s its charm and it’s surprisingly well-geared for business travelers. There’s a large tech and science industry presence via Heidelberg’s university and nearby companies, so if you need a coworking space or meeting room, places like Breidenbach Studios or design offices at Dezernat 16 can be booked. Otherwise, settle into a café like Coffee Nerd or Jesuitenkirche Café. Quiet, with Wi-Fi and caffeine to fuel those spreadsheet sessions.
One big advantage: nature is at your doorstep. Had a stressful call? In 10 minutes you can be hiking the Philosophenweg or jogging along the Neckar river path, clearing your mind with gorgeous scenery.
Also, consider using this trip to burn some Miles & More points if you’ve got them. Lufthansa operates frequent flights to Frankfurt and a quick connecting train gets you to Heidelberg. Intra-Europe, you can redeem Miles & More for as low as 15,000 miles round-trip in economy on Lufthansa or even 9,000 miles on Eurowings for some routes (they often run promos like “Meilenschnäppchen”).
All in all, Heidelberg is a reminder that slowing down can inspire you. You might return to work not only refreshed, but with your creativity recharged from walking in the footsteps of poets.
Under Bologna’s endless porticoes, every turn feels cinematic , lamplight glowing on ancient stone, the echo of footsteps on cobbles. In this “red” city of arches and towers, you half-expect to bump into a character from a Fellini film en route to a late-night espresso.
Why Go
If you love the Dark Academia aesthetic but also live for great food and offbeat charm, Bologna is your movie set. Often overshadowed by Rome or Venice, Bologna is an unsung hero, a city of shadowy medieval porticoes, old universities, and fantastic cuisine. Dubbed “La Dotta, La Rossa, La Grassa” (The Learned, The Red, The Fat for its university, red-hued buildings, and rich food), Bologna offers an intoxicating mix of intellectual and indulgent. Home to the oldest university in Europe (founded 1088), it has educated poets and popes, and its streets teem with students on bikes. The two leaning medieval towers (Asinelli and Garisenda) give a quirky skyline that screams “climb me for a view!”.
In September, Bologna buzzes with renewed energy as students return, but it’s not touristy, you’ll feel part of the local rhythm, sipping aperitivo on a piazza among Italians. The weather is still warm, perfect for evening strolls under those famous portici. Bologna has 40 km of arcaded sidewalks – great for all-weather wandering. And the food… mamma mia. From fresh tagliatelle al ragù (real “Bolognese”) to mortadella and Parmigiano Reggiano, every meal here is an event. If cities were films, Bologna would be a sensuous Italian art-house flick with witty dialogue , think less blockbuster, more cult classic that you’ll rave to your friends about.
5-Day Itinerary Highlights
Day 1: Medieval Marvels
Start in Piazza Maggiore, the heart of Bologna. Gaze at Basilica di San Petronio, an unfinished Gothic giant with a striking half-marble, half-brick facade, like it’s wearing a half-finished costume. Step inside to see the meridian line on the floor , science and art intersecting from the 1600s. Next, visit the Archiginnasio, the first seat of the University of Bologna. Its highlight is the Teatro Anatomico, a 17th-century anatomical theater all in wood where surgeons once taught. Morbidly fascinating and oh-so dark academia. At noon, follow your nose to Mercato di Mezzo or Quadrilatero, Bologna’s historic market streets. Grab lunch standing up like locals: maybe a few slices of mortadella, some Pecorino cheese, and a warm crescentina (fried bread) from a deli. After fueling up, it’s tower time. Tackle the Torre degli Asinelli – 498 steps up this leaning tower (yes, Bologna has leaning towers too!) and you’ll be rewarded with a panorama of terracotta rooftops and rolling hills beyond. You can even see all the way to the Alps on a clear day. Back on solid ground, reward yourself with gelato at Cremeria Cavour or Gelateria Gianni (because why not two scoops after those steps?). In the evening, join the locals for aperitivo. Head to Via Pratello or Piazza Santo Stefano – order a spritz or local Pignoletto wine and enjoy the free snacks that come with it. Aperitivo in Bologna often means a generous buffet of bites; it’s a budget traveler’s dream and a social ritual.
As darkness falls, walk under the porticoes of Via dell’Indipendenza and Via Zamboni – the illuminated arches create a tunnel effect that feels like a scene in a classic Italian film.
Day 2: Cuisine & Curiosities
Today, dive deeper into Bologna’s food culture, arguably Italy’s best. Start with a cooking class in the morning (many local hosts will teach you to make fresh pasta by hand – roll up those sleeves!). If that’s not your speed, consider a food walking tour: sampling aged balsamic vinegar, prosciutto di Parma, and handcrafted gelato while hearing tales of Bologna’s gastronomic history. In the afternoon, walk off the feast with some culture. Check out Museo di Palazzo Poggi, an eclectic museum of the university with everything from ancient maps to anatomical wax models, both scholarly and slightly creepy (in a cool way). Or visit the MAMbo (Museum of Modern Art) to balance out all the history with contemporary creativity. By late afternoon, take part in a beloved local tradition: the evening stroll (passeggiata). Wander under porticoes through Via Farini and Via d’Azeglio, maybe popping into Libreria Coop Zanichelli, a beautiful bookstore in an old theater. Dinner tonight is a must-do: book a table at Osteria dell’Orsa (famous for authentic tagliatelle al ragù) or Trattoria Anna Maria (home-style cooking). Savor every bite, you’re literally in the birthplace of Bolognese sauce, after all. End the night at Osteria del Sole, one of Italy’s oldest taverns (opened 1465!). It’s a no-frills wine bar where you bring your own food (leftovers welcome) and make friends over regional wine at communal tables – the perfect low-key Bolognese evening.
Day 3: Porticoes to San Luca
Time for a pilgrimage of sorts. In the morning, set out to conquer the Portico di San Luca, the world’s longest portico. It’s a covered arcade of 666 arches (spooky number intentional) stretching nearly 4 km from the city gate up to the Sanctuary of Madonna di San Luca on a hill outside town. Walking it is a quintessential Bologna experience. You’ll pass locals on their daily jog or heading to church, and each arch is numbered so you can track progress. At the top, catch your breath, admire the basilica (often a site of local devotion and festivals), and enjoy a sweeping view over Bologna and the countryside. You can cheat and take the tourist train up if needed, but walking feels more rewarding. Treat yourself after with a hearty lunch back in town. Perhaps lasagna verdi (Bolognese lasagna with green spinach pasta) at Trattoria da Gianni.
For the afternoon, indulge your intellectual side: visit Biblioteca Salaborsa, the public library in Piazza Maggiore. Not only is it a beautiful space to relax or work (free Wi-Fi, reading rooms in an ornate historic building), but under the glass floor in the lobby you can see excavations of ancient Roman Bologna – layers of time right beneath you. If you’re a music lover, the International Museum and Library of Music is a hidden gem, with exhibits on famous composers and a gorgeous music library. Tonight, go “campus mode”: wander Via Zamboni (the university quarter) and grab a casual bite like pizza al taglio or a piadina flatbread from a street vendor. Then maybe catch a performance. The Teatro Comunale often has opera or orchestra concerts or find a student theater play for a dose of Italian language and drama. Even if you don’t speak Italian, the passion on stage transcends words.
Day 4: Day Trip to Ravenna or Modena
Bologna’s central location in Emilia-Romagna means field trip! Dedicate a day to one of the region’s other stars. Ravenna (1h15 by train) will wow you with its Byzantine mosaics. The Basilica di San Vitale and Galla Placidia mausoleum are like stepping into a glittering jewel box of gold and sapphire glass. It’s an art historian’s dream and feels quite romantic in a historical sense. Dante Alighieri is buried in Ravenna, adding poetic gravitas.
Alternatively, head to Modena (30 min by train) for supercars and vinegar, tour the Ferrari Museum or a traditional acetaia to see how balsamic vinegar is made (and taste the real deal 25-year-old balsamico, liquid gold!). Modena’s UNESCO-listed pink marble Duomo and its fresh market (Albinelli) are delightful to explore as well. If food is your focus, another option is a guided food tour to Parma (for parmesan cheese and prosciutto), your taste buds will sing arias.
Return to Bologna in the evening happily sated with culture and/or cuisine. Since it’s your last night, splurge a bit: maybe reservations at Caminetto d’Oro or Al Pappagallo, upscale eateries beloved by Bolognesi and visiting celebs alike. Toast with a glass of Lambrusco (the local sparkling red wine, fun and frizzante) to your Italian adventure.
Day 5: La Dolce Vita, Bologna-Style
On departure day, soak in final impressions. Have a leisurely breakfast at Pasticceria Gamberini, one of the oldest pastry shops in town, a cappuccino and a creamy custard-filled cornetto make a perfect Italian morning. If there’s time, pop into Santa Maria della Vita church to see the dramatic terracotta Compianto sculpture (the emotional expressions on these 15th-century figures are striking). Take one more walk through the Quadrilatero market area, it’s busiest in mornings with vendors hawking produce and locals shopping. Perhaps grab some edible souvenirs: aged Parmigiano Reggiano, balsamic vinegar, or a pack of handmade tortellini for later. As you roll your suitcase down the porticoed streets to the train station or airport bus, take one last mental snapshot: Bologna’s faded red walls, graffiti mixing with Latin inscriptions, a gust of garlic and tomato from a trattoria prepping lunch, the distant toll of church bells and laughter of students. It’s a city that doesn’t show off at first glance, but gets under your skin, a fitting end scene for your European movie escapade. Ciao, bella!
Solo & Logistics
Bologna is friendly and safe, with a laid-back student-driven nightlife and a local population that takes genuine pride in their city. As a solo traveler, you’ll blend right in, perhaps mistaken for a university student or researcher. Petty crime is low; just usual awareness in busy markets and around train stations is advised. The city is well-connected by train . Bologna Centrale station is a major hub with high-speed trains, so getting here from Milan (1 hour), Florence (40 min), or Rome (2 hours) is a breeze. If flying, Bologna’s Guglielmo Marconi Airport (BLQ) is 20 minutes away; the new Marconi Express monorail will zip you straight to the station. Once in town, you can walk almost everywhere within the historic center thanks to those endless porticoes sheltering you from sun or rain. For farther flung spots (like the San Luca hill if you don’t want to walk the whole way back), the city buses are reliable – a single ticket is about €1.50 (valid 75 minutes), or get a day pass.
Bologna also offers cheap bike rentals and is quite bike-friendly. Consider renting a bicycle to feel like a local student. Language-wise, English is not as universally spoken as in big tourist cities, but most younger folks and anyone in hospitality will know enough. And Bolognese people are so warm that communication by smiles and hand gestures works too.
A nice perk: many museums and churches in Bologna are free or low-cost, so your sightseeing budget stretches. Just note that Italy observes afternoon riposo (siesta) even in cities, some shops and eateries close for a couple hours around 1-3pm, so plan your big lunch accordingly (not a problem in the food capital!).
Where to Stay
Bologna has fewer big-chain hotels, which is actually a plus for an authentic experience.
While there’s no Hyatt or Hilton in Bologna proper, Marriott runs the AC Hotel Bologna (a modern business hotel ~15 minutes walk from center). It’s not in the old picturesque part, but it’s near the train station and has the predictable comforts (and points earning/redemption). If you have a free night certificate, AC Bologna could be a practical choice. For a more atmospheric stay, consider Grand Hotel Majestic “Già Baglioni” – the only 5★ luxe in town, with frescoed ceilings and impeccable service (part of Leading Hotels of the World, which you can book via certain credit card portals for points).
Mid-range charmers include Hotel Corona d’Oro*(elegant, in a prime location by the Two Towers) and Al Cappello Rosso (boutique hotel since 1375 – yes, that’s not a typo!). These offer a boutique vibe that suits the city’s personality. If you’re keen on using H-Hotels or NH Hotels, the NH Bologna de la Gare near the station is convenient and often has good deals. And for the budget-conscious, Bologna has well-rated hostels like Dopa Hostel where you can still get a private room, great to meet fellow travelers (perhaps other solos to join for dinner so you can order all the dishes to share!). When booking, note that Bologna’s hotels can fill up during big trade fairs and university events (it’s a major fair city), so plan ahead if your dates coincide with those.
Bleisure Perks: Working remotely from Bologna might spoil you for life. Imagine logging off a conference call and immediately stepping out to snag a gelato or espresso from the café next door – that’s la dolce vita. Many hotels and cafes offer reliable Wi-Fi. If you need dedicated workspace, TIM W Capus is a centrally located coworking hub that even offers day passes. But honestly, a quiet corner in the grand Salaborsa Library could be your office. There’s something inspiring about working amid Italian students and surrounded by history under a glass dome. Also, Bologna’s strategic location means if you have meetings in Milan or Florence, you could still base in Bologna and day-trip via high-speed train to those cities, wild idea, but doable given the short ride. That’s for the truly ambitious who want to double dip destinations.
Using points to get here is a cinch: Italy is well-covered by major airline alliances. If you’ve got Amex Membership Rewards, transfer to MilleMiglia or even Flying Blue (Air France/KLM) to fly into Bologna or nearby Florence. Europeans with Miles & More can easily hop Lufthansa to BLQ.
For hotels, since big loyalty options are few, consider using credit card travel portals for boutique stays. And don’t forget, your American Express Platinum (if you have one) gives you Global Lounge Access – so you can enjoy a cappuccino in the airport lounge on your way home, already reminiscing about your trip.
FAQs (Frequently Asked Questions)
Q1: Is September a good time to visit these European cities?
A: Absolutely. In many ways, September is the best time. The summer tourist rush dwindles, so you’ll enjoy shorter lines and often better prices on hotels and flights. Weather is generally mild to warm: think low-to-mid 20s °C (70s °F) in the day and cooler, pleasant evenings. For example, Prague in September offers creative festivals and an almost autumnal festive atmosphere without the chill. Edinburgh has crisp air and clear skies once the August rains pass (pack a light jacket). Importantly, each of these cities has a university or cultural scene that wakes up in September (Late September to October for Germany). You’ll catch new art exhibits, concerts, and the buzz of students coming back, which adds local energy. Do bring layers (a light sweater or scarf) and an umbrella for the odd rain shower. And note, daylight is still decent (sunset around 7–8pm in early Sept, a bit earlier later in the month), giving you ample time for evening strolls. All in all, you get the best of summer and autumn combined. If your schedule is flexible, aim for early-to-mid September for the sweet spot of nice weather and fewer crowds.
Q2: How can I use my points and miles to save money on these trips?
A: There are tons of ways to leverage loyalty programs for a nearly-free (or at least much cheaper) escape. Here are some strategies:Flights: If you have Amex Membership Rewards, consider transferring to airline partners for Europe flights. For instance, Iberia Plus often lets you fly US East Coast to Europe in business for 34,000 Avios one-way, which is a phenomenal sweet spot. Flying Blue (Air France/KLM) also has monthly promo awards (sometimes 25%–50% off awards to Europe). If you’re based in Europe, short-haul flights on BA or Lufthansa can be redeemed via Avios or Miles & More; e.g., a one-way with Eurowings (Lufthansa’s low-cost) might run as low as ~9k Miles & More miles. Don’t overlook US domestic programs too – United MileagePlus, Delta SkyMiles, etc., all fly to these cities or nearby hubs. Pro tip: Check point.me or AwardWallet for sweet spots to specific countries. Also, if London is part of your trip (for Oxford, perhaps), note you can use Avios for the Eurostar train now that it’s partnered with Eurostar again, a cool way to hop the Channel.
Hotels: All the cities mentioned have options to redeem major hotel points. Marriott Bonvoy – use points or free night certificates at Courtyard Oxford, Augustine Prague (approx 50k pts/night standard), Glasshouse Edinburgh (Category 6), AC Hotel Bologna, etc. Hilton Honors – Waldorf Astoria Edinburgh (Caledonian) can be booked for ~60k–95k points a night, Hilton Prague ~50k/night, and Hilton Heidelberg ~40k–60k (since it’s new, deals pop up). World of Hyatt – Andaz Prague (Category 5, around 20k pts), though Oxford/Bologna lack Hyatts. H-Hotels doesn’t have its own widespread points program outside Germany, but they sometimes partner with Wyndham or others, so check if you can credit those stays. Remember, if you have a Chase Sapphire Reserve or similar, using the Chase travel portal at 1.5x value might get you a great deal at boutique hotels that aren’t points-eligible.
Other Hacks: Use airline miles for upgrades if you buy economy – e.g., upgrade Lufthansa flights with Miles & More or United miles (if Star Alliance). Some programs like Amex Fine Hotels & Resorts (for Platinum cardholders) can offer 3rd or 4th night free deals at luxury hotels, plus perks like free breakfast and property credits. This can be huge in expensive cities. And if you have credit card travel credits (like the Chase Sapphire $300), use them! Perhaps on a GetYourGuide tour or train tickets, many cards code those as travel.
One more tip: look into rail passes if you’re covering multiple countries (Eurail Global Pass), not exactly points, but sometimes you can redeem credit card points for those via a travel portal or offset the cost with a Capital One “erase” style redemption.
In short, plan ahead, be flexible with routing, and let your points work for you. You might end up only paying taxes and fees on flights and nothing on hotels, leaving more budget for food and fun!
Q3: I’m traveling solo – are these romantic cities going to feel awkward if I’m by myself?
A: Not at all! The term “romantic” here is as much about the atmosphere as it is about actual couples. Think romanticism in the artistic sense: beauty, emotion, inspiration – all of which you can absolutely enjoy solo. Each of these cities is very solo-traveler friendly. You won’t be the only person alone at that viewpoint or museum, trust me. For instance, Prague and Edinburgh are popular with solo backpackers and digital nomads, so you can easily meet people on walking tours or at hostels if you want company. Oxford and Heidelberg being university towns mean there are plenty of solo academics and travelers around – you’ll blend in as someone maybe doing research or just exploring. If anything, being solo can heighten that “main character in a movie” feeling. You can be spontaneous, follow your own schedule, and maybe even have a Before Sunrise-style chance encounter (who knows!). Safety-wise, as covered, these cities rank high. Prague feels safe day and night in tourist areas, Edinburgh too. In restaurants, especially in Italy or France, don’t shy from dining solo. The staff are used to it and will often give you a nice seat. Bring a book or journal to cafés if you like, but honestly, there is so much people-watching and ambience to soak up, you likely won’t need extra entertainment. Plus, without a travel partner, locals often engage more – you might end up chatting with that friendly barista or an elderly couple on a bench. So embrace the solo experience. In romantic cities, you get to fall in love with the city itself – a relationship that can be just as fulfilling.
Q4: How can I effectively mix business and leisure on a trip like this (any tips for bleisure)?
A: Great question. Balancing work and play is an art! Here are some practical tips to master the bleisure life:
Schedule Smart: Try to stack your work obligations together, leaving full days free. For example, if you have to work a few half-days, see if you can compress into 2 full workdays, then take 3 days fully off for exploring (or vice versa). Use time zone differences to your advantage: if you’re from the US East Coast and in Europe, your mornings are wide open (until calls start around 2-3pm Europe time). Sightsee in the morning, then work late afternoon/evening. In contrast, if from Asia, you might sightsee in afternoons. Plan a rough outline before you go so you don’t get caught in a beautiful castle at 3pm with a conference call you forgot about.
Leverage Remote Tools: Make sure your accommodation has reliable Wi-Fi. Many hotels offer high-speed internet, especially business-oriented ones (Hilton, Marriott, etc., typically do). Don’t hesitate to ask for a quiet room or business center access if you need it. Cafés are great for casual work, but for serious calls you might use coworking spaces (Day passes are a thing in most cities – e.g., Impact Hub in Prague, WeWork in many capitals, etc.). Keep time tracking apps if needed to ensure you’re meeting your hours while still enjoying travel.
Set Boundaries: When it’s work time, focus and get it done efficiently so you can log off and be present in the city. Conversely, when it’s leisure time, try to unplug. If you use a work phone/laptop, maybe leave it in the hotel safe during your off hours so you’re not tempted to check email while sipping wine on the Old Bridge. Let colleagues know your schedule too – e.g., “I’ll be available 2pm-8pm CET for calls, offline otherwise exploring Edinburgh.” Usually, they’ll respect that (and maybe be a tad jealous!).
Bleisure Activities: Take advantage of the “leisure” part in small bites if needed. For example, on a workday in Oxford, stroll a nearby park or college for a 30-minute lunch break, it refreshes you more than scrolling your phone. Or do an early morning activity (like Arthur’s Seat hike at sunrise in Edinburgh) before a 9am meeting. You’ll feel accomplished and energized. In many European cities, evenings are vibrant, so even after a full workday you can go to a concert, join a night walking tour, or have a long dinner al fresco. You won’t feel like you missed out just because you worked 9-5. The city comes alive after 5 too.
Extend Weekends: Try to position your work trip adjacent to a weekend. For instance, fly in Thursday night, work Friday on-site (if it’s a meeting or just remotely), then have the whole weekend free before needing to be back Monday afternoon. Or stay the weekend after. A 2-day vacation tacked onto a work trip can feel like a bonus mini-holiday with very little extra cost (maybe just a couple hotel nights since your flight was covered by work or points).
Mind the Taxman: One practical note – if you’re extending a work trip for personal fun, check your company’s policy. Usually, it’s fine and you just separate personal expenses. But ensure you follow any guidelines for travel insurance, etc., if you go off on personal time. Also, if traveling internationally for work, make sure your visa allows leisure; generally yes in these countries, business visa or Schengen visa covers tourism too.
In summary, plan ahead, communicate, and be disciplined when working so you can fully embrace not working. Bleisure is all about those “wow” moments in between emails and trust me, a beautiful European backdrop makes even replying to emails feel a bit nicer.
Q5: What are some must-pack items or preparation tips for these destinations in September?
A: Packing for a multi-city Europe trip can be tricky, but here are some tips and must-haves:
Versatile Layers: Early fall weather can vary. Pack a light jacket (a denim or leather jacket works for style and cool nights), a cardigan or hoodie, and a mix of short and long sleeve shirts. A travel umbrella or rain jacket is wise, especially for Edinburgh and Oxford which can see rain. Comfortable jeans or trousers plus maybe one nicer outfit if you plan a fancy dinner or theater night.
Walking Shoes: Cobblestones are everywhere. High heels will punish you (and get stuck!). Opt for stylish yet comfy sneakers, flat ankle boots, or walking shoes. You’ll likely walk far more than at home. In Prague or Bologna you might easily do 15k steps exploring those winding streets.
Daypack or Tote: Bring a lightweight backpack or tote bag for day trips and carrying your essentials (water bottle, camera, work laptop if needed, souvenirs). Many European cities have banned single-use plastics, so having your own refillable water bottle is great to stay hydrated cheaply and carry your shopping home.
Travel Adapters and Tech: All these countries use the European Type C/E/F plugs (UK is different – Type G). A universal adapter with USB ports helps charge multiple devices. If you have many Zoom calls, maybe pack a portable laptop stand or noise-cancelling headphones to make any café your office. A power bank is useful for long touring days to recharge your phone (especially if you’re using it for Google Maps and photos constantly).
Local SIM or eSIM: Consider getting a local SIM card or an eSIM plan for Europe to have data on the go – great for maps, translation, rideshare, etc. Alternatively, check if your phone plan has free roaming in Europe (T-Mobile US, for example, does albeit slow speed). Wi-Fi is abundant in cafes/hotels, but having 4G data everywhere is a game-changer for spontaneity.
Advance Tickets/Reservations: Prep-wise, book certain popular attractions in advance to save time. For example, Edinburgh Castle timed tickets, Oxford’s Bodleian Library tour, or a Last Supper at Santa Maria delle Grazie if you detour to Milan (not in our main list, but you get the idea). Also, if you’re keen on specific restaurants (like that one famous traditional osteria in Bologna or The Witchery in Edinburgh), reserve a table ahead.
Medicine and Health: Pack a small kit with any meds you need, plus some basics like ibuprofen, motion sickness tablets (if you do boat tours or get train-sick), and Imodium/Tums just in case of any food adventures gone wrong. Pharmacies are easy to find, but it’s nice to have what you need on hand in a pinch. And don’t forget travel insurance, especially since you’re mixing business/leisure, ensure you’re covered for both health and any work equipment you bring.
Space for Souvenirs: You will shop, even unintentionally. That cute tartan scarf in Scotland, vintage book in Oxford, wine in Prague, or parmesan cheese in Bologna… Leave a little room in your luggage or bring a packable duffel. Worst case, you can mail things home (but that’s pricey). Better to pack light initially and fill up as you go. By preparing well, you’ll travel confidently and minimize those “dang, I wish I had ___” moments. And remember – almost anything forgotten can be bought there, often at similar prices. So don’t stress too much; focus on comfortable clothes and shoes, and the mindset to explore. Bon voyage or, as they say in Italian, buon viaggio!
Ready for your European escape that feels straight out of a film? 😎 Whether you’re walking Prague’s Charles Bridge at sunset or catching a glimpse of yourself in an Oxford shop window (wondering which period drama you stepped into), these cities are sure to ignite your sense of adventure and keep you on track with your career. That report due Monday might be written from a café in Heidelberg with a view of the castle. How’s that for work-life balance? So go ahead: plan that trip, embrace the bleisure lifestyle, and let Europe’s romantic cityscapes inspire your inner storyteller.
If you found this guide helpful or daydream-inducing, be sure to subscribe to our newsletter for more travel tips and tales. Your next journey – and “main character” moment – awaits. Safe travels and happy daydreaming! ✈️🌍
London – the dream of many a traveler and a city of contrasts.
I am of the firm opinion that everyone should visit London at least in their life. Read along to learn why and what there is to see in this famous city.
Disclosure: Some of the links in this post are ‚affiliate links‘. This means if you click on the link and purchase the item, I will receive an affiliate commission.
The classics
No week in London without at least some sightseeing.
You will start your trip with the absolute royal experience: by visiting Buckingham Palace. Arrive in the morning for Change of Guards or any time a day for a view of the building. Prepare for crowds, no matter the time. If you’re lucky you timed your visit with the yearly opening and catch a glance inside. From there its easy to get walk through St. James Park and see the Horse Guards. Whitehall and Westminster are a short walk away. Here you‘ll visit famous Westminster Abbey*, see Big Ben and House of Parliament.
From here head east towards Tower Bridge along the river Themse. The South Bank with popular London eye* and many a street artist is perfect for a walk. Stop by Borough Market and cross London Bridge into the City of London proper. Catch your first glimpse of Tower Bridge and visit St. Paul‘s Cathedral* on the way to the Tower.
My absolute favourite sight to visit was Tower of London*. I spent so much time walking all the parts and visiting every corner I could and it was absolutely worth it!
Cross Tower Bridge and head to Shakespeares Globe for some poetic vibes. Watch a show if possible.
I love getting around in London with public transportation and use my Oyster card everywhere. But you could also chose to use the Hop-on-hop-off busses to visit the different sights. These will probably take you two days to take it all in.
A walk in the park
London is a metropolitan city but still offers lots of greenery.
Classically you could head to Notting Hill, get a feel for the movie, or visit Kensington Palace and the Gardens. I would also suggest a walk through Hyde Park. Feel a little bit of these Bridgerton vibes there and imagine yourself strolling down these ways during that period.
From there its back to the busy streets via Convent Garden and into brilliant SoHo. From here its not far to Trafalgar Square, Piccadilly Circus and Leicester Square. Perfect to visit in the evening and visit a show in West End.
If you chose to see some calmer streets, head to Hampstead, walk around Camden and visit Granary Square and Regent‘s Canal while your on the road. This would be perfect to see King‘s Cross as well.
London is the place if you want to feel like royalty. Various locations offer afternoon tea in movie-like atmosphere or you could try tea time on the river Themse during a cruise.
Mayfair, the Ritz, the Brown‘s Hotel*, there’s literally an afternoon opportunity for every taste or budget.
Visit the royal palace at St. James‘s or stroll through Regent‘s park. There is so much to see if you want the full royal experience.
Outside the city
Leaving the inner city for a day trip or even for half a day is a very fun thing to do if you have the time.
Enjoy a boat cruise to Greenwich and visit the royal observatory* and the campus of old naval college.
You could even combine it with an afternoon tea cruise. It’s been an absolute joy to get the first glance from the river and then enjoy walking and exploring from there.
If your heart longs for the English countryside, with its cottages and cobblestone streets, visit the Cotswolds. Just a short ride away and everything your cottagecore heart needs. I love seeing them in autumn, but its worth it any time.
A royal lover will probably love a trip to Windsor with Windsor castle* the seat of the royal family. So definitely enjoy this experience your trip!
Knowledge and experience
London offers some amazing free museums, that are always worth a visit. From famous natural history museum, to the science museum and the Victoria and Albert museum, you could spent days just visiting all the museums of the city. Outernet is also worth a visit.
For all the Harry Potter fans it’s not only a must to visit King‘s Cross, but also the Leavesden studios to see the World of Harry Potter. Definitely worth it and take an extra SD for all the photos you will take there.
The metropolitan London
London is also a very modern city. For all the urban feeling you should visit Canary Wharf or Battersea Power station.
I also recommend visiting one of the many sky bars and get a feel of the skyline from in the city. I recommend skipping the shard and heading to Sky Garden or OXO Tower.
Visit Bank to see the corporate side of London and enjoy an afterwork drink or food here.
No idea what and how to plan and nothing is really to your liking? Do you have special requirements and no idea how to find what you need? Chat me up at Instagram @AstheticofJess and I’ll help you plan your next dream trip.
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