The 8 Best Airbnb Experiences in Tokyo for Immersive Adventures

Imagine weaving through Tokyo’s neon-lit streets, the hum of the city alive around you, as you uncover hidden gems with locals who know every secret alley and whispered story. That’s the magic I chase on my adventures, and after backpacking through national parks and collecting passport stamps from over 30 countries, Tokyo remains my ultimate playground. With my recent van life conversion making off-grid trips a breeze, I’ve returned to this vibrant metropolis about 10 times, each visit revealing layers of food stalls, hidden shrines, and quirky subcultures. One of the best ways to dive deep? The best Airbnb experiences in Tokyo, led by passionate residents who turn standard sightseeing into unforgettable immersions. These aren’t your cookie-cutter tours—they’re hands-on journeys into the heart of Japanese culture, history, and nightlife. Whether you’re a first-timer or a repeat explorer like me, these experiences offer educational insights wrapped in pure fun, helping you connect with Tokyo’s endless depth in ways solo wandering just can’t match.

In this guide, I’ll share my top 8 best Airbnb experiences in Tokyo, drawn from personal favorites and backed by traveler reviews from high-DA sites like Nomadic Matt and Airbnb’s own listings. We’ll explore why they stand out, what you’ll learn, and how they fit into broader travel trends like sustainable and authentic tourism. Plus, I’ll weave in tips from my van life hacks, like packing light for urban explorations, and recommend gear to elevate your trip. For more on budget-savvy adventures, check out our post on how to travel on a budget in 2025. Let’s embark on this journey to rediscover Tokyo’s spirit—one experience at a time.

Why the Best Airbnb Experiences in Tokyo Beat Traditional Tours Hands Down

The best Airbnb experiences in Tokyo shine because they’re hosted by locals or long-term expats who infuse each activity with personal stories and insider knowledge, creating connections that feel genuine and enriching. Unlike larger group tours, these are often small-scale, allowing for tailored interactions and deeper dives into topics like izakaya etiquette or tea rituals. According to traveler feedback on sites like Viator and GetYourGuide, Airbnb’s model emphasizes cultural immersion, with 4.9+ ratings for many Tokyo offerings. This approach aligns with 2025’s travel trends toward experiential and eco-conscious trips, where visitors seek to support local economies while learning sustainably.

From my own escapades, these experiences have transformed my visits—turning a simple walk into a history lesson or a meal into a culinary masterclass. They’re educational too, teaching about Japan’s blend of tradition and innovation, much like the global exchanges in cannabis as a tool for self-knowledge and ethical living. If you’re planning a trip, prioritize ones that match your interests; they’ll make Tokyo feel like home. For similar vibes elsewhere, explore the ultimate travel guide to Italy for first-timers.

Mastering Sushi: Hands-On Class with a Pro Chef Among the Best Airbnb Experiences in Tokyo

Dive into the art of sushi with this standout among the best Airbnb experiences in Tokyo, held in an authentic omakase restaurant. Led by a seasoned sushi master or their apprentice, you’ll learn not just rolling techniques but the philosophy behind each slice—why fish cuts vary for texture, how rice seasoning adapts to styles, and pairing secrets for ultimate flavor harmony. It’s a morning session, perfect for a hearty, interactive breakfast before hitting the streets.

What makes it educational? You’ll grasp sushi’s cultural roots, from Edo-period origins to modern sustainability practices, as highlighted in reviews on Tripadvisor. Small groups ensure personalized tips, and you’ll leave with skills to impress at home. During my last Tokyo stint, this experience fueled my van life meals—fresh, simple, and mindful. Book this sushi-making class directly on Airbnb for an unbeatable start to your day. Pair it with a portable cooler for market hauls, like the one I use on road trips.

tripadvisor.com

2025 Tokyo Sushi Making Class in Tsukiji with Professional Chef …

Caption: Participants crafting fresh sushi under expert guidance in a Tokyo class, one of the best Airbnb experiences in Tokyo.

This hands-on approach demystifies Japanese cuisine, teaching respect for ingredients and precision—lessons that extend to everyday cooking. For more foodie insights, see our quick Mediterranean chicken rice bowl recipe.

Unlimited Vibes: Shibuya Nightlife Tour Tops the Best Airbnb Experiences in Tokyo

For an electrifying evening, this Shibuya nightlife tour ranks high among the best Airbnb experiences in Tokyo. Hosted by the charismatic Suemi and her team, it whisks you to 3-4 untouristy izakayas buzzing with locals, offering unlimited drinks and bites. My guide Shugo’s energy kept the group engaged, sharing izakaya culture—from casual ordering to toasting traditions—while extending the fun beyond scheduled time.

Educational gems include understanding Japan’s social drinking norms and how these spots foster community, as noted in Klook reviews. It’s upbeat and social, ideal for solo travelers or groups. On my recent trip, it echoed the camaraderie of my national park hikes—shared stories over shared plates. Don’t miss their sake tasting variant, delving into production with visuals for easy comprehension; it’s the best I’ve tried. Secure your spot on Airbnb now—spots fill fast. Carry a compact flashlight for those dimly lit alleys, the exact one I pack for van adventures.

klook.com

3 Hour Shibuya Local Bar & Izakaya Crawl Evening Tour in Tokyo …

Caption: Group toasting at a hidden izakaya during a lively Shibuya tour, highlighting the best Airbnb experiences in Tokyo.

This experience also offers whiskey tastings, broadening your palate knowledge—perfect for tying into exploring pop piano techniques for a cultural fusion night.

Sake Secrets: Shinjuku Izakaya Hop Among the Best Airbnb Experiences in Tokyo

Similar in spirit but uniquely flavored, this Shinjuku izakaya tour secures its place in the best Airbnb experiences in Tokyo. Guided by sake sommelier Yuma, you’ll navigate narrow alleys to tiny, local spots, sampling diverse sakes while learning menu navigation and ordering etiquette. Yuma’s outgoing style makes complex topics like sake grades and pairings accessible and fun.

It educates on izakaya’s role in Japanese social life, from post-work unwinds to seasonal celebrations, per Magical Trip insights. Relaxed and immersive, it’s a gateway to Tokyo’s nightlife without overwhelm. Recalling my van life solitude, this communal vibe refreshed my spirit. Book this Shinjuku adventure on Airbnb for an authentic taste. A reusable water bottle keeps you hydrated between sips—the insulated one I swear by for long hauls.

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What’s Japanese Sake!? Shinjuku Izakaya Bar Hopping!【Guided Food Tour in Tokyo,Japan】

Caption: Exploring cozy Shinjuku izakayas with sake pours and local bites, a top pick for best Airbnb experiences in Tokyo.

For more on global flavors, link to most beautiful Caribbean islands to visit in 2025 ranked explained.

Time Travel: Historic Walking Tour as One of the Best Airbnb Experiences in Tokyo

Step back in time with this historic walking tour, a gem among the best Airbnb experiences in Tokyo. Focusing on quieter neighborhoods like Yanaka, your history-specialist host unravels tales of the Edo period, samurai evolutions, and Meiji-era shifts. Visits to Nezu Shrine’s torii gates and old streets provide vivid context, making 2.5 hours fly by with insightful narratives.

Educational depth shines through, teaching Tokyo’s transformation from feudal hub to modern marvel, as detailed on Viator. It’s uplifting, connecting past to present in a walkable format. During my backpacking days, it mirrored discovering hidden trails—unexpected revelations at every turn. Reserve this enriching stroll on Airbnb today. Comfortable walking shoes are key; grab the pair I use for urban explorations.

viator.com

Yanaka Walking Tour: Historic and Traditional District of Tokyo

Caption: Wandering through Yanaka’s historic paths and shrines on a guided tour, embodying the best Airbnb experiences in Tokyo.

This ties into broader wonders, like ultimate guide to the wonders of the world ancient natural and new.

Brew Awakening: Tokyo Coffee Culture Tour in the Best Airbnb Experiences in Tokyo

Uncover Tokyo’s thriving coffee scene with this tour, a flavorful entry in the best Airbnb experiences in Tokyo. Roaming under-visited areas like Jimbocho and Kanda, you’ll sample from vintage kissaten to third-wave spots, learning brewing methods, flavor nuances, and Japan’s meticulous coffee evolution.

It educates on cultural pairings, like wagashi sweets with brews, fostering appreciation for everyday rituals, per Perfect Daily Grind. Thoughtful and unique, it’s a relaxed afternoon boost. Echoing my morning coffee rituals in the van, it recharged my wanderlust. Sign up for this caffeinated journey on Airbnb. A travel mug keeps your tastes fresh—the exact one I rely on for on-the-go sips.

perfectdailygrind.com

Japan: 3 of Tokyo’s Must-Visit Specialty Coffee Towns – Perfect …

Caption: Sampling artisanal coffees in cozy Tokyo cafes during a culture tour, one of the best Airbnb experiences in Tokyo.

For wellness ties, see benefits of cold plunges explained.

Zen Sip: Organic Matcha Tea Ceremony Among Best Airbnb Experiences in Tokyo

Embrace serenity with this organic matcha tea ceremony, a tranquil highlight of the best Airbnb experiences in Tokyo. In just an hour, learn matcha’s history, societal role, and quality discernment, then whisk and savor in a peaceful setting far from the city’s frenzy.

Educational and meditative, it reveals tea’s philosophical depths, from Zen influences to preparation artistry, as explored on Mai-ko.com. Short yet impactful, it fosters mindfulness. Like my off-grid reflections, it grounds you amid travel excitement. Join this ceremony on Airbnb for a soulful pause. An electric kettle simplifies home recreations—the one I use in my van setup.

mai-ko.com

TEA CEREMONY IN JAPAN – Tea Ceremony Japan Experiences MAIKOYA

Caption: Whisking vibrant matcha in a traditional ceremony, capturing the essence of best Airbnb experiences in Tokyo.

Link to inner peace with finding calm in everyday moments.

Slurp Mastery: Tokyo Ramen Tour as a Flavorful Best Airbnb Experience in Tokyo

Indulge in ramen’s diversity with this tasting tour, a savory staple among the best Airbnb experiences in Tokyo. Over three hours, sample styles from classic to fusion at multiple shops, uncovering origins, trends, and regional twists.

It educates on broths, noodles, and toppings, building culinary confidence, per Tokyo Ramen Tours. Come hungry—it’s filling and fun. Reminiscent of my trail-side meals, it celebrates simple joys. Book this ramen adventure on Airbnb. Insulated bowls preserve heat; try the set I pack for picnics.

tokyoramentours.com

Ultimate Ramen Tasting Tour | Tokyo Ramen Tours

Caption: Tasting steaming ramen bowls on a guided Tokyo tour, a delicious best Airbnb experience in Tokyo.

For recipe ideas, check spicy chipotle salmon tacos and slaw.

Urban Canvas: Shibuya and Harajuku Street Art Tour in Best Airbnb Experiences in Tokyo

Discover Tokyo’s underground art scene with this street art tour, an edgy favorite among the best Airbnb experiences in Tokyo. Exploring Shibuya and Harajuku’s murals and installations, learn about restrictions fostering creativity, with before-and-after visuals for context.

Educational on Japan’s subtle graffiti culture, it’s intriguing and offbeat, as per Tokyo Cheapo. It reveals hidden sides, much like my national park discoveries. Reserve this artistic walk on Airbnb. A sketchbook captures inspirations—the one I carry on trips.

tokyocheapo.com

Art In Unexpected Places: Harajuku Street Art | Tokyo Cheapo

Caption: Admiring colorful street murals in Harajuku during a tour, showcasing best Airbnb experiences in Tokyo.

Tie to creativity with exploring the world of resin art.

Planning Your Tokyo Trip: Logistical Tips to Maximize the Best Airbnb Experiences

To make the most of the best Airbnb experiences in Tokyo, book flights via Skyscanner for deals, accommodations on Booking.com for affordability, and don’t skip travel insurance from trusted providers. For multi-destination hops, the Japan Rail Pass saves heaps—essential for exploring beyond Tokyo.

Neighborhood breakdowns help: Shibuya for energy, Yanaka for history. My van life tip: Pack versatile layers for variable weather. For more planning, visit our best day trips from Toronto for 2025 top 24 escapes.

Essentials List: Gear to Elevate Your Tokyo Adventures

Here’s my curated list of must-haves for seamless travels—each tested on my global jaunts:

1. Portable Solar Charger – Keeps devices powered during long tours.
2. Insulated Water Bottle – The exact one I use for hydration on the go.
3. Reusable Silicone Bags – Eco-friendly storage for snacks, currently 30% off—run.
4. Noise-Cancelling Headphones – Blocks city noise for focused experiences.
5. Compact Flashlight – Illuminates hidden alleys at night.
6. Travel Mug – Perfect for coffee tour takeaways.
7. Sketchbook – Captures art tour inspirations.

These picks turn trips into smooth sails—grab them before your departure.

Tokyo’s best Airbnb experiences unlock doors to authentic joy and discovery. For more, explore Nomadic Matt’s full guide.

P.S. Ready to plan your dream itinerary? Sign up for my free travel planner download—exclusive tips and checklists straight to your inbox.

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My lungs burned as I bent forward, gasping, my hands on my hips. I had known that the air would be thin at 11,800 feet, but I was surprised at just how tough the altitude was making my climb to Chhema Lake. Still, I was hiking in the Mustang District of Nepal, so my temporary struggle was worth it: I was surrounded by the Annapurna range of the Himalayas, where peaks glistened in the sun and mini avalanches sent snow down distant chutes.

The adventure reminded me of a trip to Bhutan a few years ago, when I made the two-hour trek to the famed cliffside monastery known as the Tiger’s Nest. The Himalayas have become for me—and for a growing number of travelers—the antidote to city living and work stress. A trip to what some call the roof of the world is an opportunity to unplug, slow down, and swap screens for prayer flags flapping in the wind.

In recent years, the region has also been transformed by the opening of luxurious, design-centric hotels in places where high-end lodging has historically been nonexistent. These thoughtfully conceived escapes, all new since 2023, emphasize cultural immersion—an alternative to the “peak bagging” crowds that have choked up routes to some of the Himalayas’ legendary summits. Nepal, for example, has lately notched record-setting international arrivals, and the country’s tourism board describes Everest Base Camp as “extremely popular.”

Read on for a closer look at some of the best lodging in the region, as well as the outdoor activities and community-conscious tours they can unlock.

Bhutan

Known for its Gross National Happiness concept and unspoiled natural beauty, in 2022 the country inaugurated the 250-mile Trans-Bhutan Trail, which is open to both day hikers and serious trekkers. While brands including Aman and Six Senses have been long-standing fixtures in Bhutan, newer on the scene is Pemako Punakha, which has 21 luxurious tented villas, each with a private pool. Guests can access the trail, meditate with the resident Buddhist monk, go whitewater rafting on the Mo Chhu river, and visit the picturesque Punakha Dzong, a centuries-old fortress. In Paro, Dawa at Hilltop by Heeton is the country’s largest hotel, with 87 rooms featuring private balconies and views of the surrounding peaks; its indoor pool is a nice amenity after a flight into Paro International Airport, the country’s sole international gateway.

India

The Himalayas stretch across a huge sweep of northern India, making it a challenge to know where to start. One enticing option is traveling with the tour and guesthouse operator Shakti, which has pioneered community-centric tourism in states including Uttarakhand. Shakti Prana, for example, is a new lodge reachable only by foot. It has seven rustic-chic stone cottages where yoga, meditation, and hikes in the surrounding countryside are the main activities. To the northwest, in Himachal Pradesh, Sitara Himalaya has 10 suites looking out over the Dhauladhar range that have bright Banarasi silk walls, handwoven pashminas in every room, and under-floor heating. A part of Relais & Châteaux since 2024, it also arranges excursions, such as waterfall hikes and visits to Hindu temples.

Nepal

The climbing capital of the world, Nepal has been luring mountaineers for decades, including up the busy South Col route to the summit of Mount Everest. But a more culturally rich experience can be found at Shinta Mani Mustang, a 29-suite lodge from prolific hotel designer Bill Bensley that has floor-to-ceiling views of Nilgiri Himal, which tops 23,000 feet. Daily outings take guests to alpine lakes and nearby villages; a Tibetan-medicine doctor can help guests work out any altitude-related aches and pains. To the southeast, the latest addition to the Mountain Lodges of Nepal portfolio is Deboche, a 13-room lodge situated above 12,200 feet—but below the iconic Tengboche Monastery, with its showstopping views of Everest and the surrounding summits.

Tibet

Traveling to the Tibet Autonomous Region, which is part of China, can be difficult for Americans: at a minimum, visitors need both a Chinese visa and the assistance of a specialist tour operator to handle other formalities. The U.S. Department of State estimates that fewer than 10,000 Americans make the trip annually—but those who do will find the trend toward more interesting, higher-end accommodations has also touched this corner of the Himalayas. Songtsam Linka Retreat Lake Basong Tso, for example, is situated on an emerald lake surrounded by towering peaks. The hotel has 122 rooms and access to activities such as monastery visits, incense making, hikes, and cycling.

A version of this story first appeared in the October 2025 issue of Travel + Leisure under the headline “The High Life.”

For Travel + Leisure’s column Traveling As, we’re talking to travelers about what it’s like to explore the world through their unique perspectives. Burnt out from corporate America, Kelly Benthall got her finances in order and gave up her Texas lifestyle to retire at 53 and live around the world in Airbnbs with her husband, Nigel. Here’s her story… 

I was living in Texas and working in oil and gas. As time went on, and the kids left, my job became extraordinarily stressful—to the point that I had to be wheeled out on a gurney through the lobby, hooked up to an EKG. After all those years of feeling like I needed to overachieve, my doctor said my job was trying to kill me.

Once I realized that, my husband, Nigel, and I got a financial advisor who gave us some sound projections and advice. I always thought I would retire at 65 and play golf. Nigel didn’t have a retirement plan. He was going to work forever, and it took me a couple of years to get him to turn the corner. But at 53 years old, I decided to retire. 

Once the job went away, all my stress dissipated and my levels returned to normal.

I wasn’t raised traveling. Our family would take our modified van from Texas to Ohio every year to see my grandmother—that was our big trip. I didn’t even have a passport until I got married the first time in my 20s, and we just went to Mexico. Eventually, at work, I said yes to every single trip that came up because I was interested in seeing the world. I love foreign languages and talking to people from different countries. One time, one of my contractors was pregnant and couldn’t go to Kalimantan, Indonesia. I knew nothing about what she was doing, but I went anyway.

I find travel quieter and calmer [than being at home]. I’m attuned to every little thing because it’s new and different, so I relax and take it in. I am not a playground tourist—I don’t go to all the major tour sites. I might walk by and walk in, but I like just hanging out at a cafe and chatting with people.

While I have lots of friends and family in Houston, it’s not ultimately where I wanted to be, sof when Nigel and I both retired, we got the idea to travel the world, living for a month at a time in Airbnbs. 

We started with a trial run in 2023, spending a month in Mexico to make sure we could actually live with just each other. At the time, we had been married for about seven years.

We stayed in the middle of the jungle in Tulum in a very intimate space—the door between the bedroom and kitchen was glass, so there was no privacy at all. But we did Pilates on the roof together every morning and cooked dinners. We bought a Christmas tree and decorated it. And we did a great job—I was very proud of us. So we came back and started planning our global travels. 

I watched all the YouTube videos I could find and listened to people’s advice. Initially, I went to some local real estate agencies, but I like places that have local flair. What I found is that Airbnb, more than other platforms, is good with that because we can connect with local hosts. Plus, we can search easily for things that are important to us, like outdoor space. We’ve had some nice places with rooftop pools that weren’t expensive. Being able to see all the ratings and not having to sign a lease makes it easy. 

It’s also been affordable. We’re now staying in this place in Aix-en-Provence, where we’ve been for eight weeks, and got a 70 percent discount for a long stay. So we could stay for a week somewhere, or we could stay for six weeks for the same price. I thought, how did no one ever tell me about this? That really is the thing that’s made this all possible, and I’m grateful for it.

We started in Dubrovnik, and took Nigel’s 87-year-old mom with us. It was interesting because the language is so different. We did a walking tour with someone who spoke English so we could get the lay of the land. The city was amazing, like a movie set. We learned to walk up and down its hills. We stayed in a neighborhood that had these local bodega-type shops. The older guys would play buće (bocce) in the evenings, and we would go out and sit with them. 

We asked our Airbnb host what we could do for the community even though we don’t speak the language, and ended up helping harvest grapes at this small winery. They can’t hire too many people because of tax issues, so they rely on volunteers. It was hot and difficult work, but a fun way to learn about the culture. 

Since then, we’ve also picked up trash on beaches in Mauritius. When you’re a tourist, you might not think about it, but when you’re visiting for longer, it’s different. That’s one of the things that helps us connect with the locals. They know we’re not just using and leaving. We hope to get more involved with our community work. We would eventually like to work with kids, but we’ll have to stay longer to earn that trust and get the language down. 

When we get to a new place, we’ll usually start by finding a local market. We’ll explore and find the things locals do. In Seville, for example, we were across the street from a community center, so we’d go and see all the classes people were taking. It was easy to get involved with the neighborhood because they would all gather outside in the evening, so we joined them. That’s usually how we acclimate ourselves.

We also like to walk around and get lost. Since we’re in places for so long, we have time to ask around. A few times a week, we’ll do day trips. The other day, we took the train to Avignon and went wine tasting in Châteauneuf-du-Pape. 

In Mauritius, we got really close with our Airbnb host. They lived across the street and invited us over to use their property. We spent New Year’s Eve with them. It was just lovely. We stayed in Lecce for a month and would drive to the different coasts. We spent a few days south of there, and I met a woman who took my photograph from behind while I was watching a sunset and drinking a glass of wine. She invited us to a dinner party the next night, so we extended our stay. No one spoke English, except for one kid. We sat in the middle of the table with the hosts, and everyone sat as far away as possible because they knew we didn’t speak the same language. But by the end, we were able to communicate using Google Translate and through the child. That was memorable, and I still keep in touch with them.

I find comfort in spreadsheets, so we use one to plan our travels. It’s color-coded following the sun by region. Then, I have the cost of living compared to the U.S. We also don’t want to spend a ton of money on flights, so we pick a general area. Right now, we’re doing Europe, and we do a bit of the Schengen shuffle if we need to because we can’t stay too long. 

Nigel’s family is in England, so it’s been our jumping-off point. We have six kids, and one daughter, two grandkids, and Nigel’s mom are all there. Our other kids are in California, Utah, and Texas, so we do a U.S. round for about three months. 

We stay in each place for at least a month to get the discount. We wanted to spend some more time in Provence because neither of us had been, so we’ve been in the region for three months now. Next, we’re going to go back to England since I’ve never seen my husband’s home country. Then, we’re going on a road trip and will spend a month in Ireland. Airbnbs there are about $65 a night, pretty cheap. You can’t even get some hostels for that amount.

We could stay in bed-and-breakfasts on this road trip, but I don’t want to be put together and mingle all the time. I need my own space and a kitchen. We cook all the time with ingredients from the local markets. It saves us money, and it gives us a lot of privacy, which we don’t get in hotels. In Mauritius, we did go to a hotel for a nice meal on Christmas Eve, and I was like, “Oh, I forgot how nice hotels are because everyone is serving you rather than serving yourself.” But I don’t think I could live in a hotel.

After that, we’ll go back to the spreadsheet and feel it out. I know we want to go to Asia, then New Zealand. We also want to go to Bali and South America. We’ve got all of these big-picture plans.

There are definitely challenges. I miss our friends and family, and being able to drop in on people. We always book a place with an extra room so we can have people visit. But it can also be a bit isolating if we don’t make an effort.

It’s not just being in another country. Being retired is weird at this age. At first, I felt a little guilty doing nothing. Now, I realize it’s OK to be bored. I enjoy it. I’ve gotten a lot more creative in this chapter, a lot more introspective. Nigel always wants to go and do things, and I have to remind him, we’re here for a long time. You don’t need to see everything right away. We’re not here as tourists. We’re here as kind of locals, while also doing a bit of touring.

People will ask where we’re from, and that’s a complicated answer. They also ask what we do—not so much overseas as they do in the U.S. We’re fortunate to have this lifestyle, but it’s difficult to explain to people in a way that doesn’t sound braggadocious. I tell people we’re looking for places where we belong in the world and are exploring and looking for adventure.

My background is in behavioral psychology, so I like that I get to walk in the shoes of other people and understand their perspectives. It’s been eye-opening. In Texas, we say hello to everyone. In places like France, people are super-friendly, but they’ll say bonjour and that’s it. They don’t automatically become friends with you. It depends on where we are in the world. 

Once we spend a month in a place, it feels like home. We always feel like we should spend more time there because just when we’re getting to the point where we know where everything is, it’s time to go. We have our local wine bar and fishmonger, and it’s time to leave again. We can’t stay during the high season because it’s expensive and I don’t like crowds.

I’ve found observing and absorbing cultures to be very unifying. The world is giant, but also so small, and traveling really teaches us respect. I have so many friends and family members who just don’t understand what we’re doing. But if everyone would just go and explore, it would break down these perceived barriers we all have. You realize people have stereotypes about you that may not be true. I can’t force my interests on other people, but I do feel strongly about it and think it’s something everyone should do.

It was a warm June afternoon in Bucharest. Rays of sun bounced off the glass of Romanian-produced rosé that I’d held up to clink above the table. Over a soundtrack of loud house music, Martha Butterfield, a vivacious 84-year-old with wispy silver hair, giggled naughtily and shouted, “Live your f@*#ing best life!” 

She wasn’t giving a toast. She was reading from a piece of art hanging on the wall of the restaurant, Casa di David. But the words would have made a fitting mantra for my weeklong cycling adventure with Butterfield & Robinson, an active-travel company founded by Martha, her brother Sidney Robinson, and her husband, George Butterfield. Joie de vivre has been B&R’s driving force since its early days in the 1960s planning bike trips from Vienna to Paris. 

While Western Europe itineraries remain among the company’s most popular, George, 85, thrives on forging tracks in less-discovered corners of the world. Romania, with its Easter-egg-colored Saxon villages, Gothic castles, medieval citadels, and forested valleys, is his latest obsession. Five-star accommodation is a feature of any B&R itinerary; in the past few years, the opening of properties like Bethlen Estates and Matca have allowed George to curate high-end trips there. 

I joined George, Martha, and 12 of their longtime clients on a newly created trip that started in the vibrant capital, explored wine country, and ended in Transylvania, a cycling mecca. “Here’s to a week of discovery,” George toasted, adding with a wink, “Thank you for trusting me.” “I’d follow you anywhere, George,” yelled Andy Gleeman, a B&R groupie on his 11th trip.

It’s not all long mileage and steep climbs—B&R journeys prioritize cultural immersion. To that end, we began with a history lesson. After lunch, Raluca Şpiac, of the travel agency Beyond Dracula, gave our group a glimpse of the country’s Communist years, from 1948 to 1989. She took us to Ferestroika, an apartment turned private museum that felt like a time capsule from the 1980s, complete with a pantry sparsely stocked with monthly rations. In contrast, the mansion of Romania’s notorious final Communist rulers, Nicolae and Elena Ceaușescu, was the epitome of extravagance, with velvet- and silk-lined walls, a gilded bathroom, and a private cinema. 

“The Ceaușescu times were particularly traumatizing,” Şpiac said. “But Communism forced people to be very creative.” We witnessed that ingenuity in everything from the edgy pieces on display at the Museum of Recent Art to the open-fire cooking that evening at Bucharest’s Soro Lume restaurant. George ranked the meal among the best of his life, and he’s traveled to 51 countries and owns a home in Burgundy, France. Palates don’t get more discerning.

The phrase “Never Underestimate an Old Man With a Bicycle” was emblazoned on the back of George’s cycling jersey, and I spent much of the next day staring at it as I pedaled behind him. In this group of rugged B&R veterans, at 44, I was the youngest guest. E-bikes allowed those in their 70s and 80s to breeze past me on the rolling, vineyard-covered hills of Dealu Mare, one of Romania’s premier wine regions. Our 18-mile route led us to the tasting room of LacertA winery, where we learned about the country’s dark-skinned native grape, Fetească Neagră.

Grapevines gave way to the soaring peaks of the southern Carpathian Mountains as a van transferred us three hours northeast to Brașov, a medieval city in Transylvania. It has several historical monuments—most notably one of Romania’s largest Gothic buildings, the Black Church—but also modern cafés and bistros. At One Soul, we ate tender duck breast dressed in a deliciously funky sauce with pear and yuzu. 

Over the next few days, as we cycled through pastoral landscapes speckled with bell-shaped haystacks and well-preserved Saxon villages, it felt like we’d traveled back to preindustrial times. (The Communist years left much of the countryside undeveloped.) A slower pace allowed me to observe shepherds tending their flock, women fetching water from wells, and men steering horse-drawn carts. Ponies munched grass on the side of the road, and white storks nested atop farmhouses. 

Transylvania is home to people from more than a dozen different ethnicities, and people we passed spoke both Germanic and Hungarian dialects. We would come across whitewashed Unitarian churches in one village, then towering Gothic or Romanesque Lutheran churches in the next. 

On the fourth day, an hour-long ride led us to the village of Alma Vii, which was founded in the 13th century. The fortified church and its surrounding stone walls have been restored, and it now houses the Center for Interpretation of Traditional Culture. Inside, craftspeople braided corn husks for mats and made felt woolen slippers and hats. 

A local restaurant, Belalma Rural, had brought a farm-to-table feast to the center, and we dug into hearty plates of sautéed lentils with oven-baked eggplant and ricotta-like urdă cheese. Palincă, a fruit brandy served with every meal, flowed freely, and the group teased me—the “youngster”—when I abstained. “But this is the B&R way,” insisted Dick Balfour, one of the five lawyers in our group.

Even with 20 to 30 miles of cycling a day, I was still feeling the trip’s indulgences, so I’d committed to biking the optional 11 miles back to our hotel, Bethlen Estates, in the medieval village of Criș. That evening, we’d been told, the property’s super-talented chef would be serving us a seven-course dinner of updated Hungarian recipes, like fermented cucumber with fresh peas and smoked trout and dill, served with a cold cucumber gazpacho. I intended to be hungry. 

Bethlen Estates was the ancestral home of Count Miklós Bethlen, who passed away in 2001. Since then, his widow, Countess Gladys Bethlen, has been meticulously restoring the property with ambitions of making it Romania’s most luxurious place to stay. I’d say she succeeded—not a detail was missed, from the fresh-cut flowers in my bedroom, which was warmed by a traditional tiled stove, to the handmade ceramics in the dining room.

Székely Land, where we spent our final two days, is an area in the eastern Carpathians where many ethnic Hungarians live. The cultural distinctions made it feel as if we’d cycled across a border: at our hotel, Zabola Estate, a fairy-tale property in Zăbala owned by a Hungarian noble family, the staff spoke Hungarian, and we dined on dishes like goulash and kürtőskalács, a spit-cooked, sugar-dusted pastry we hadn’t been served anywhere else. 

My legs were finally starting to feel the miles, so after an afternoon ride I wandered down a forested path (watching for bears as I went) to Zabola’s sauna and cold plunge. I returned to the terrace at sunset to find our group clinking glasses of plum palincă. After a week with George and Martha, I left convinced that the secret to living your best life is simple: good food and good wine, friends, and a view. 

A version of this story first appeared in the July 2025 issue of Travel + Leisure under the headline “Joy Ride.”