How a 2-week Trip to Tokyo Changed My Mind About Solo Travel

I’m sitting alone at a record bar in Tokyo, sipping a dirty martini and willing someone to talk to me. It’s been more than 24 hours since I’ve spoken out loud; body language and the bizarre magic of Google Translate have been my only modes of conversation. As a hyper-extrovert, I’m going a little wild — and it’s more than just the 'tinis talking (if only they would).

"I really like the music," I type on my phone, watching my words reappear in Japanese and wishing my personality translated as easily. I slide my screen across to the bartender with a pitifully earnest facial expression, clearly craving human interaction. He offers me a smile and quickly returns to garnishing a cocktail. I want to say, "Where do I go to make friends?" I want to say, "This is my first time traveling alone and I’m a little lonely, but mostly awestruck by this kaleidoscopic city, and I wish I could talk about it in a non-computer generated voice." Instead, I open my mouth and tip back the last of my drink, crossing my fingers into an X because the internet told me that’s how to signal for the check here. In Japan, my words and gestures are not my own, and yet I feel closer to myself than I have in months. 

I set out on my first-ever solo trip a week ago — 12 days in Tokyo and Kyoto, where I know no one and can’t speak a word of the language — in a bid to push myself as far out of my comfort zone as possible. I’ve been traveling full-time for a year, primarily with friends and family in French- or Spanish-speaking places where I have some linguistic leeway. Most of my trips have been with a parent, partner, or close friends, meaning I’ve rarely found myself alone.

That hasn’t bothered me much: I’ve always preferred my alone time in brackets. I’m glad to spend the day writing or wandering on my own, so long as I know I’ll meet a friend that evening. So when I decided on nearly two weeks alone in Tokyo to celebrate my 29th birthday, I worried about the open-endedness of all that me time. What if I don’t like myself as much as I like my friends? What if I’m a less savvy traveler when I don’t have someone to explore with? And worst of all, what if I get overwhelmed by all the restaurants I’ve starred on Google Maps and don’t have someone to help decide where we should eat? The responsibility of being entirely in charge of my own itinerary seemed daunting.

But traveling alone ended up being one of the most fulfilling, empowering experiences I’ve had during this nomadic year. Alone in a country and in a language I had absolutely no bearings in, I started to reconnect with myself. The endless sprawl of Tokyo meant I could never "see it all," so I quickly gave up on the instinct to pack things in and instead let myself be carried along by the current, taking long, meditative walks through old-school neighborhoods like Yanaka and along the river in Nakameguro. Moments of loneliness were overshadowed by unexpected sparks of connection, like swapping travel stories at a sushi counter or hopping through wine bars with local friends I met on my last night. 

For all the ways solo travel intimidated me — and for all the moments I wished I had someone to talk to and process the experience with — it ultimately gave me more confidence in myself as a traveler, helping me feel simultaneously more self-sufficient and open to relying on the kindness of strangers. It taught me that certain things — like an umami-packed first bite of uni or the musical creaks of 400-year-old floorboards in a Kyoto castle — can’t be translated, so sometimes it’s best to put down your phone and just appreciate them in silence. 

If you’re planning a trip to Japan, here are some of the places in Tokyo and Kyoto that changed the way I think about dining, sleeping, and wandering on my own. 

Tokyo

Aman Tokyo

After touching down in Tokyo in the evening, I headed straight to Aman Tokyo, a secluded oasis tucked away from the city’s bustle. After crashing early, I woke the next day at sunrise and made a choice I would never have dared to with a travel companion: I didn’t leave the hotel. That’s right, I flew 14 hours to spend an entire day inside. Hear me out: A few too many recent attempts at overextending myself at the start of a trip had convinced me to take it easy on day one, allowing myself to adjust to the jet lag and get ahead of some deadlines. And it wasn’t exactly a chore to hole up in my sun-drenched, 1,517-square-foot suite with beautiful blonde wood, delicate washi paper doors, heated bathroom floors, and panoramic views of the glittering city from the bathtub. 

After knocking out some work, I made my way to the hotel’s heated pool, where I had tantalizing skyline views entirely to myself. Already starting to relax, I indulged in a restorative Signature Spa Journey — a full-body scrub and massage that erased any damage my flight had done — before taking full advantage of Aman’s luxurious spa amenities, including an onsen-style hot bath and a steam room. It was the best thing I could have done for myself to start the trip on a positive note, and it taught me an important lesson from the get-go: Listen to your body. I knew I needed a day to reset, despite the voice in my head telling me I should be exploring immediately. When you’re traveling with others, compromise is the name of the game; alone, there’s no need to people please. 

The Tokyo Edition, Toranomon

There’s perhaps no better view of Tokyo than from one of the 206 guest rooms and suites at The Tokyo Edition, Toranomon. Designed by Japanese architect Kengo Kuma, the Ian Schrager hotel is as dazzling to look at as it is to look out of: Rooms are elegant and understated, with minimalist furnishings in natural wood tones and luxuriously comfortable beds. Suites on the upper levels boast their own private terraces, all the better to admire the stunning skyline. I spent my last night here, wrapped in a plush bathrobe and gazing out at the Tokyo Tower as I reluctantly packed my bags. 

Locale

OK, I lied — I know exactly one person in Tokyo, and they happen to be the chef of one of the coolest farm-to-table restaurants in the city. I met California native Katy Cole in France last fall, when we worked the wine harvest in Chablis together. When she suggested I look her up if I were ever in Tokyo, the idea sounded so far-fetched that I immediately put it out of my mind — until a few days before my trip, when I asked if she’d be free to get together and, ideally, eat. We ended up spending several days together, including a night at her charming, intimate restaurant in Tokyo’s Meguro neighborhood. 

It’s hard to overstate Locale's cozy and convivial atmosphere: Sitting at the counter around her open kitchen, it felt like pulling up a stool at a friend’s home — one who has excellent taste and an extensive knowledge of local Japanese produce, which is front and center on the rotating chalkboard menu. Alongside a solid selection of natural wines, I tried everything on the menu that night, from an avocado and French lentil dish spread atop a shock of pink yogurt (colored by the Japanese pickle shibazuke) to roasted pork with local cabbage. The meal ended with a homemade buttermilk pecan cake drizzled with a crème anglaise so good that it brought tears to my eyes — or maybe that was just my delight at having found such a wonderful new friend in Katy. (But seriously, the cake was fantastic.) 

Ginza Sushi Ojima

One of the worst parts of traveling alone is not having someone to share food with. I love eating by myself, but as just one person, I can’t try as many dishes as I would with a companion. This dilemma was solved entirely by my first-ever omakase experience, a meal built entirely around single-bite courses. Walking into Sushi Ojima in Ginza, which is hidden in a nondescript office building, I felt like I’d found my way into a secret club. I hardly knew what to expect: I’d pre-paid for a 13-course nigiri lunch at the intimate 12-seat counter and I’d brought a book, thinking I’d want to keep myself entertained, utterly unaware that I was about to witness one of the most beautiful works of culinary theater I’d ever seen. 

With fluid movements, the chef sliced fresh cuts of fish into sculptural perfection, dabbing on freshly grated wasabi or sprinkling sakura salt before pressing them into mounds of rice. I was mesmerized. I was drooling. I was unsubtly eyeing the Japanese couple next to me each time we received a new course, trying to gauge if I was meant to use chopsticks or my fingers. It was one of the moments I most wished I could communicate out loud about what a life-altering moment my taste buds were having, as my mouth closed around a sunset-colored squid and I ate a veritable school of tiny white fish with pink eyes. 

Afternoon Tea at Four Seasons Hotel Tokyo at Otemachi

Tea is an indelible part of Japanese culture, and getting to taste a variety during Sakura Afternoon Tea at the Four Seasons Hotel Tokyo at Otemachi was a palate-expanding experience. While the sweet and savory sampler was delicious — raspberry and pistachio opera cakes and tiny bites of duck breast wrapped in a cucumber crepe with maple cream — it was the tea that delighted me the most. That, and the view of Mount Fuji in the distance.

Curry Spice Gelateria Kalpasi

Almost impossible to find, this curry shop and gelateria (a culinary combination I was thrilled to discover existed) sits at the end of a small alley in the ultra-hip Shimokitazawa neighborhood. To order, you warily eye a vending machine labeled with the Japanese menu, then look positively helpless until someone comes and kindly points out that you select the top row to order either two or three of the daily-rotating curries and a fragrant mound of jasmine rice; the next row includes can’t-miss sides like Japanese pickles and coconut sambol; the third is to add on gelato. While the curries are mouthwatering, the gelato is what’s truly worth writing home about: They’re pepped up with various curry spices, so you can expect flavors like coconut with charred mustard seeds and kaffir lime, chocolate and Sichuan pepper, or mascarpone with cardamom and lassi. 

TeamLab Planets Tokyo

There are few places that combine culture with unbridled childlike joy like TeamLab Planets. The interactive museum — a favorite of celebrities like Justin Bieber and Dua Lipa — is a full-body experience that begins by removing your shoes and shuffling up a vertical waterfall. Making my way through the exhibits, I was struck by how much fun everyone was having. Sure, it’s an Instagram hot spot, but in between snapping curated photos, every single person was grinning and looking around the space with wonder. 

It was invigorating to watch adults be so, well, silly — and how could you not be when you’re asked to crawl alongside a group of strangers on a mirrored floor as a ballet of fragrant orchids dances overhead? Or, when you’re told to bump into enormous color-changing globes? Each room holds new visual and tactile surprises, be it the Infinite Crystal Universe — a dazzling, Kusama-esque mirrored room of LED lights — or the shin-deep pond of warm water, where vibrantly projected koi fish interact with bodies in real time. The museum is a memorable experience that’s a must-see in Tokyo. 

Kyoto

Aman Kyoto

After picking up a Japan Rail Pass at Tokyo Station — which allows unlimited travel on the Shinkansen, the high-speed bullet train, to just about anywhere in Japan for a set duration of seven, 14, or 28 days — I snagged a seat on the next train to Kyoto (be sure to ask for a seat with a view of Mount Fuji).

Two hours later, I was met by a driver from Aman Kyoto, who whisked me 30 minutes north to the meditative retreat set in a lush, secluded garden that’s been extraordinarily maintained for decades. The property is a natural marvel, carved out with mossy stone paths studded with tall trees and lit by candles at night. The ryokan-inspired rooms are a striking marriage of modern design and ancient tradition, with floor-to-ceiling windows that give way to a view of the green glades. With two restaurants and an indoor-outdoor onsen, I found it hard to tear myself away. 

Minimalist and peaceful, my room — in particular, the enormous hinoki bathtub — was the perfect place to rest and reset after long days of touring temples in Kyoto. While I was mesmerized by all of the famous sites — Nijō Castle, Daitoku-ji Temple, Arashiyama Bamboo Grove, and Fushimi Inari were a few favorites — I was most moved by the private temple tour and tea ceremony the hotel organized for me. This offered unparalleled access to a centuries-old tea room and a one-on-one lesson with a Japanese tea master. 

Sake Bar Yoramu

For a crash course in sake, make a pilgrimage to Yoram Ofer’s exceptional eight-seat bar in downtown Kyoto. As a natural wine lover with no knowledge whatsoever of the fermented rice beverage, I was enthralled when I walked in and found him patient and passionate in his explanation of flavor profiles and producers. 

He opened the bar back in 2000 and has been aging much of his sake since then, serving his vibrant, invigorating beverages by the glass so that you can taste a wide variety — everything from fruity, unpasteurized styles to ambered vintages — a number of which he heated up for me to try side by side.