From Desk to Departure: How I Planned My Trip to Japan

Admittedly, I hadn’t come across TRUNK before planning this trip, but it immediately stood out when I was digging through hotels that consistently impressed reviewers — including verified Michelin Guide guests, who rate it a 19.5 out of 20. After spending time there, I can say without hesitation that it’s one of my all-time favorite hotels. Celebrating my birthday in the Dining Suite is a core memory, thanks in no small part to the team’s thoughtful touches.

This is exactly the kind of property I flag when planning a trip: carefully vetted, stylish and smartly located, among other things. If you’re wondering where I started when I began plotting my Japan itinerary, it’s a mix of trusted guides, review cross-checking and a lot of note-taking. TRUNK is a perfect example of that process paying off.

Condé Nast Traveler called OMO3 Tokyo Akasaka “the best it gets for cheap digs souped up with cheerful service and great access to the surrounding neighborhood and beyond.” And they’re right. What makes OMO properties stand out is their programming, which leans heavily into the local neighborhood, a feature I always look for when planning a trip. It’s the kind of place that turns a convenient, well-priced stay into a mini-immersion in the area, giving you a sense of place without the guesswork.

For the last night of our trip, I had originally booked an airport hotel, thinking that after two weeks of traipsing across Japan, we’d be tired and appreciative of Haneda’s proximity. But at the last minute, I pivoted and booked The Four Seasons Tokyo at Otemachi (not to be confused with its neighbor, Four Seasons Hotel Tokyo at Marunouchi), and I cannot overstate how grateful I was for that decision. Forbes calls it a four-star property — which, by definition, means “an exceptional property, offering high levels of service and quality of facility to match” — and it absolutely lives up to that.

When I plan trips, I often leave a little room for last-minute upgrades like this.

OMO, in my opinion, has some of the best on-site offerings out there. While hotel-sponsored activities can sometimes veer into the kitschy, OMO hotels lean niche and hyper-local. As one TripAdvisor guest put it, “The free guided tours of the local area really helped with settling in and seeing some hidden gems.”

We tried the Amazing Akasaka Walk, which takes you to spots most tourists wouldn’t know to visit — including Norainu, where the proprietress, a former geisha, greets you with homemade drinks. It was basically an OMO crash course in the neighborhood, and we loved it so much that we signed up for a second tour later in the week.

For anyone mapping out a trip, experiences like this are really good jumping off points: Local immersion built right into the hotel stay, making it easy to see and do more without extra planning stress.

I’m not afraid to admit that being a travel editor hasn’t made me immune to social media or whatever’s trending at the moment. TeamLab had been flooding my feeds for years, so a visit was all but inevitable. I mean, here’s a fashion influencer I’ve followed for a decade discovering TeamLab Planets earlier this year. Here’s Kim Kardashian.

In other words, I was influenced. Luckily, it very much lived up to the hype. And when I’m planning, I usually sprinkle in experiences like this, the ones that are almost impossible to ignore online but are genuinely worth it in person.

I love a market and will cram as many as possible into an itinerary. You can learn so much about a culture just by wandering its stalls. Take Ameyoko, for example. According to the Japan National Tourism Organization, “Ameyoko became a huge marketplace after World War II. It started as a black market, selling many things that people who worked for the Occupation forces would get from the soldiers.”

For planning purposes, resources like this, plus videos from outlets like Matador Network, are a great way to get a feel for a market before you go — what to expect, where to focus your energy and what hidden gems might be worth seeking out.

While in Tokyo, I spotted the Mori Art Museum’s “MACHINE LOVE: Video Game, AI and Contemporary Art” exhibition on Instagram. Normally, video games and AI aren’t really my thing, but this show was genuinely spectacular. Unfortunately MACHINE LOVE closed in June, but if it’s any indication of the caliber of the museum’s current and future installations, I’ll be making a point to stop by every time I’m in Japan.

I rely heavily on previews like this — museum Instagram feeds, exhibition calendars and reviews — to decide what’s worth carving into an itinerary, especially when time is limited.

It’s worth noting that over the past decade or so, Tsukiji Market has become very touristy — according to many Japan travel-related Reddit pages, too touristy. That said, InsideHook contributor Jake Emen still calls it one of the best food markets in the world, and I trust his judgement. Guides like this from Travel + Leisure are the sort of resource I use to plan a visit deliberately, helping figure out when to go, what to focus on and how to avoid the worst crowds.

In my quest to find a traditional omakase that wouldn’t break the bank, I came across Tachiguizushi Sushikawa in the Michelin Guide. At just more than $100 a person, it felt like a steal, and for the first 45 minutes or so, we were the only ones there, turning the meal into an almost private dining experience.

Using guides like Michelin is my go-to way to uncover spots that balance quality, authenticity and value, the kind of places that make a meal unforgettable without the sticker shock.

Because we were staying at The Four Seasons, Virtù was a no-brainer. The bar has racked up accolades on top of making Asia’s 50 Best Bars list, and I can confirm it’s an absolute banger. Both the bar snacks and the cocktails — La Geisha, in particular — are unmatched. Staying on-site made it easy to take full advantage of the hotel’s offerings, from Virtù to the other restaurants, without having to plan extra trips across the city.

I’d done enough research to know that est is essential dining while staying at The Four Seasons, or anywhere nearby, really. And honestly, I still think about that meal to this day. It’s the kind of restaurant that turns an already-great trip into a truly memorable one.

I remember reading a flurry of “First Looks” in 2024, right after Banyan Tree Higashiyama opened, and immediately adding it to my list. As expected, it’s an absolute dreamboat — if we hadn’t been in Kyoto, I could’ve happily spent the entire day in my room, which even came with its own private onsen. And that’s before you even get to the rest of the amenities, which are just as thoughtfully-curated.

Nishiki is another heavily touristy market, but as one Redditor on r/JapanTravelTips put it, “Yes it’s full of tourists but it is also full of good food and neat crafts. 100% worth checking out. Make sure to try the tako tamago.”

I often look to Reddit when planning trips because the firsthand tips and nuanced perspectives from travelers who’ve recently been there are invaluable for knowing what’s worth your time and what to skip.

Whenever we travel, we always aim for one “splurge meal.” Kyoyamato, a two-star Michelin restaurant I discovered while planning, definitely fits the bill. But it’s more than just a splurge — the experience is unparalleled from start to finish: the setting, the service, the presentation, the flavors. We were treated like royalty, and ate like it, too.

I’d heard Pontocho described as a hub for nightlife in Kyoto. Going there for after-dinner drinks turned out to be a good call, especially because some reviews painted it as “just a long alley of a bunch of expensive ass restaurants.” For our purposes, it was perfect, particularly the bar serving birthstone-inspired cocktails.

During our stay at Banyan Tree, we ate at Ryozen every day. You can go for a traditional Japanese kaiseki course menu or opt for the counter chef table with a grill — either way, it’s an experience. It’s also another aesthete’s dream. I ended up ordering the red wine glasses they stock before we’d even left the dinner table on our final night.

If you’ve spent any time on Instagram planning a Japan trip, you’ve definitely seen the Arashiyama Bamboo Grove. And yes, it’s everything people say — busy, smaller than you might expect — but it’s still beautiful and fun to photograph. At the very least, you can reward yourself with a coffee on the other side.

History buffs would be remiss not to make time for the centuries-old Kyoto Imperial Palace. The palace itself is impressive, but the grounds are just as remarkable. It’s the biggest park in central Kyoto — beautiful, expansive and peaceful. Resources like this guide from Lonely Planet are great for getting a sense of what to see and how to make the most of your visit.

Ninenzaka and Sannenzaka are two of Kyoto’s most iconic streets, perfect for a leisurely stroll. Cobblestone paths, traditional shops and teahouses make it feel like stepping back in time. Instagram-worthy, yes, but also genuinely enjoyable if you go early before the crowds arrive. I paired a visit here with a quick look at travel resources like a Kyoto City tourism website, which highlights must-see stops along these streets and helps plan your route so you don’t miss the hidden gems tucked into the alleyways.

Visiting all of Kyoto’s temples would likely take years — there are more than 1,600 — so if your schedule is tighter, you have to be intentional with your picks. Kiyomizu-dera is a smart choice. It’s centrally-located so it doesn’t eat up your day, and Travel + Leisure Asia lists it as one of 12 must-see attractions in Kyoto. For planning, resources like this help narrow down priorities.

The Gion neighborhood is famous for its geisha culture and preserved-in-time vibe. I first took note of Gion while editing this piece by Jake, though this Michelin guide piece dives a bit deeper and offers more granular tips for exploring the area. It’s the kind of thing I rely on when I want both context and practical guidance for a neighborhood stroll.

I’d venture to guess this is one of the most Instagrammed attractions in all of Japan, but given its cultural significance, I wanted to see it for myself. The trick is to climb to the top — the higher you go, the thinner the crowds. By the time we reached the final shrine, we were virtually alone.

If you have a little extra time, Tofuku-ji Temple is nearby and far less crowded, with gorgeous gardens that make it well worth the detour. I usually utilize maps and local guides to pair these spots efficiently so you get the best of both without backtracking.

Whereas OMO3 is considered one of Hoshino’s “basic” hotels, OMO7 is a full-service, conveniently-located property set on a lush 7,600-square-meter lawn with all the fixings. I loved a number of the little touches here: the self-service amenity wall stocked with yukatas, the Pikapika light show and, of course, the brand’s signature immersive experiences. On top of that, they offer a free shuttle to Universal Studios, which is a handy perk if that’s on your agenda.

Kuromon Market is a street food paradise, and planning your visit definitely helps you make the most of it, so map out a few must-try stalls. That said, also leave room to explore, as there’s something new to try at virtually every turn.

We probably never would’ve found Taisho if it weren’t for OMO7’s Binge on Kushikatsu Tour, a deep dive into retro-funky Shinsekai followed by, quite literally, a kushikatsu binge. I’m so glad we did. From the outside, it’s relatively nondescript, but inside we had one of our most memorable meals — fried items in quantities I won’t even attempt to tally, all while chatting with the owner. Experiences like this really underscore the value of curated tours.

This was a relatively last-minute decision, but at the time, it was the only Nintendo World — and that was reason enough for us. The express pass is well worth the splurge and honestly necessary if you want to make the most of your visit without spending half the day in line.

Osaka Castle shows up on nearly every first-timer’s guide to the city, and even if you don’t go inside, it’s worth seeing up close because it’s an architectural marvel. If you do step inside, you’ll find more than 10,000 artifacts, including samurai gear, making it a surprisingly deep dive into Japan’s history. I like to check guides and museum resources ahead of time so I know which floors or exhibits are worth prioritizing.

When it was first built, the Osaka Aquarium Kaiyukan was famously the largest aquarium in the world. It’s since been surpassed a few times, but a colleague who lived in Shizuoka swore the whale sharks alone made it worth a visit. I’ll admit that this was the place where I felt most overwhelmed by crowds. But, like at Fushimi Inari, they eventually thin out. And yes, the whale sharks are legitimately impressive. Pro tip: Arriving early or later in the day can make a huge difference in your experience.

Matsumoto Jujo is one of the most outstanding hotels I’ve ever stayed at. The rooms are impeccably appointed — ours even came with a private onsen — and the design is utterly dreamy. The restaurant is incredible (more on that later), but the real showstopper is the bookstore tucked off the lobby. Once a public bathhouse, it’s been fully renovated into a multi-level space stocked with more titles than you could possibly read, though I spent an inordinate amount of time trying anyway.

Our stay at Fuchinobo was both insightful and deeply pleasant. In 2022, Rakuten Travel named it one of the top 10 National Temple Lodges nationwide, and it’s easy to see why. It’s no-frills — you sleep on a tatami mat with a mattress pad on top — but the monks are incredibly attentive. We were served every meal in our room (all vegetarian, following Buddhist tradition), enjoyed the onsens on the ground floor and then attended the morning service, Oasagoto, at the main hall of Zenkoji Temple. Experiences like this are why I take the time to tap trusted travel resources when planning because they make it possible to find stays that are truly culturally authentic.

Hikariya Higashi is housed in an Edo-era building, built in 1885, at the foot of the Northern Alps. The traditional coursed meals feel perfectly in step with the surroundings, making it one of those spots that’s as much about the setting as it is the food. Again, local guides and hotel websites are key in uncovering places like this that might otherwise fly under the radar.

Sanrokunana serves a pre-fixe, wood-fired menu, with dishes that the restaurant says reflect “the ever-changing climate of the Shinshu region” and highlight foods “that expose you to the two additional elements of culture and history.” It’s a very interactive experience and the kind of meal I seek out whenever I travel, one that goes beyond just taste to tell a story.

Kiso Fukushima is the kind of town that makes you feel like you’ve been transported back in time. Nestled in the Kiso Valley, it’s famous for its preserved Edo-era streets and charming inns. Wandering the area, you can get a real sense of traditional Japan, from wooden merchant houses to quiet temples tucked down side streets.

Kiso Hirasawa and Narai post town are two highlights along the historic Nakasendo Trail. Hirasawa charms with its quiet streets and traditional wooden houses, while Narai has a livelier energy full of shops, teahouses and local crafts. If time allows, I like to grab a historical account of the post towns I’m visiting from a bookstore. A little context goes a long way.

Matsumoto Castle is impossible to miss. Its black-and-white exterior and moat make it one of Japan’s most photogenic castles. Inside, the steep wooden stairs and preserved interiors give a sense of how samurai life might have unfolded centuries ago. For planning, I consulted the Japan Guide entry for Matsumoto Castle, which offers practical tips on hours, ticketing and exhibits.

Visiting the Snow Monkey Park in Nagano is one of those experiences that feels like a once-in-a-lifetime photo op, but the reality is even better. Watching the macaques soak in the hot springs, seemingly unbothered by the winter chill or the crowd of humans, is oddly mesmerizing. I referenced the official Jigokudani Monkey Park website ahead of time for the latest info on trail conditions, shuttle schedules and admission.

Should you find yourself in Nagano in late January or February, Restaurant Kamakura Village is an absolute delight. Think snow-dusted paths, cozy little igloos serving hot pots and myriad winter activities. I like to check local event calendars and seasonal guides for the lowdown on what’s happening and when crowds are lighter.

I didn’t get a chance to go inside the Matsumoto City Museum — it happened to be closed that day — but I was thrilled to see that the Yayoi Kusama exhibit was on display. Even from the outside, it’s clear the museum puts on engaging, colorful shows worth noting. And this, folks, is exactly why we plan: Checking museum websites and arts-focused publications ahead of time gives you the scoop on exhibitions, ticketing and timing so you can tweak your itinerary before you show up and leave empty-handed.