10-Night Japan Itinerary: Where Tradition Meets Tomorrow

Your immersion into the cultural wonders of Japan begins before you even touchdown, particularly if you fly Japan Airlines. We’re particularly fond of the A350-1000 aircraft with in-headrest speakers and privacy provided by the sleek sliding doors on business and first-class pods. Upon clearing arrivals, you’ll be met by your private driver for a seamless transfer into the capital, where you’ll start your Japan itinerary. 

Look forward to a soft landing at Four Seasons Hotel Tokyo at Otemachi, an oasis set thirty-nine floors high amidst Tokyo’s business district. Take in the sweeping skyline views and get ahead of jetlag by avoiding a nap, no matter how tempting. Instead, soak up the comforts of your suite, settling in by reviewing the printed itinerary left in your room by your SmartFlyer travel advisor, outlining all you have to look forward to on your eleven-day Japan itinerary.

Many international arrivals will find you getting to the hotel just before dinner time, and if you’re feeling like sticking at the property, there are options abound. We particularly love the menu at VIRTÙ, a venue notably ranked number eighteen on Asia’s 50 Best Bars for its collection of vintage French spirits and rare cognacs. While some Japanese whisky could do the trick to get you in sleep mode, if you’re interested in a more wellness-focused route, the spa offers a Deep Sleep Ritual massage that will lull you into a restful night of sleep with its nineteen essential oils.

Wake up for the first full day of your Japan itinerary, ready to tackle what is going to be a thoughtful immersion into this bustling capital city. If you’re feeling up to some morning movement, the hotel’s location just steps from Tokyo Imperial Palace makes for a seamless running route; the concierge can provide a map outlining the approachable five-kilometer loop. Then, fuel up back at the Four Seasons’ expansive breakfast before meeting your driver and guide to head out for the day. 

You’ll begin in the Asakusa neighborhood for an immediate dive into Japanese history, where the rhythm of the Edo period remains. And while you’ll have time on foot later, we’ll start this exploration via rickshaw, one of the city’s most unique forms of transportation. This Japanese “jinkiksiha” or “human-powered cart” is your key to bypassing crowds and seeing Old Tokyo the same way Tokyoites did hundreds of years ago.

Hop off to wander through Sensō-ji Temple, where your guide will walk you through the structure dating back to 645AD. After pulling your fortune and saying a prayer if you’re so inclined, wander from Sensoji’s Kaminarimon to Nakamisedori, a vibrant shopping street filled with shops selling snacks and trinkets; we love the fried pork bites from Asakusa Manchi. This will be your first time experiencing the Japanese approach to staying stationary when eating—no taking your snack on the go!

For lunch, we love Daikokuya Tempura in Asakusa. Post lunch, if you’re in the market for some new knives, a visit to Kappabashi Kitchen Town will reveal a street lined with stores catering to the needs of restaurant operators, from wax food samples used to market dishes to pots, pans, and cooking utensils. We’re partial to the knives from Musashi Japan which could be your first of many tax-free purchases while in Japan. For dinner, if you’re looking for a more informal izakaya consider Ginza Fukumini. 

This morning, if you’re keen to see the auction at the fish market, you’ll need to be prepared for a 3:30 a.m. wakeup. We happen to think you can get just as much out of a later arrival after the auction has come to an end, so if that’s more your style, don’t fret. Your foodie guides will pick you up for this special, two-part tour after breakfast—just be sure you’ve left room for the bites to come. 

You’ll begin at Toyosu Market, the world’s largest wholesale seafood market built on reclaimed land in Tokyo Bay. A symbol of the city’s appetite for constant growth and innovation, Toyosu replaced the aging Tsukiji Market in 2018 and is known for its fast-moving carts; that said, this stop isn’t recommended for young children or those not comfortable staying on their toes! This visit is possible thanks to the access brokered by your SmartFlyer travel advisor, as most parts of the market are not open to the general public.

After having the chance to be immersed in what we can only refer to as the ‘belly of the beast,’ you’ll hop in your private car for the next stop on your Japan itinerary. Tsukiji Outer Market is the more touristic market and we recommend having cash for this stop as most vendors don’t take credit card. Be sure to sample some freshly made sushi, roasted sweet potatoes, wagyu bites, and, if you’re down for ice cream before lunch, matcha Cremia.

The ultimate transition after having seen the source of the fish, lunch will be an interactive one where you’ll be learning from the best how to make your own nigiri. Master chef Udatsu is one of Tokyo’s most respected, earning a Michelin star for his innovative techniques. While you can pair yours with sake, we love that this is also one of the few places in the city that does tequila pairings.

For the remainder of the afternoon and evening, opt to either have a guide show you around to some of Tokyo’s top shopping, or do a self-guided wander through the shops. From high-fashion districts like Ginza and Omotesando to niche boutiques and under-the-radar ateliers, there’s something for everyone. Favorite Japanese brands of ours include Maison Special, Onitsuka Tiger, CFCL, and visvim. For vintage, don’t miss a stop at MixTHINKS, Paradise Vintage, and Amore. This evening’s dinner is an omakase at Sushi Yoshida.

Somehow, it’s your last full day in Tokyo before heading to Kyoto—but don’t worry, your SmartFlyer travel advisor has wisely carved out one final day here on the back end of your Japan itinerary so that you have time to return to anything you feel you missed. This morning, choose between doing a bonsai workshop with a master in his craft, or, if you’re looking for something a bit more active, a samurai sword lesson with Tetsuro Shimaguchi, the renowned choreographer who helped devise the iconic scenes in Kill Bill. If you happened to see Lewis Hamilton’s recent Instagram post, yes, that one.

From here, it’s time for a soba lunch. We love Ryan for its delicious handmade soba noodles and easy access to Shibuya. Walk over to this famous crossing, one of the busiest pedestrian crossings in the world, where traffic is stopped to allow pedestrians to cross in all directions. Your private car will be waiting to whisk you to Harajuku, the epicenter of Japanese street fashion and subculture. It’s worth wandering nearby shopping where there’s a slew of streetwear brands with an emphasis on sneakers, including Kicks Lab. 

If you’re in the market for Japanese denim, we have just the place. An appointment at Maker’s Pride of Craft (recommended to book at least one month in advance) in Daikanyama is your key to completely custom jeans. They’ll take two full months to ship back to you, so it’s one less thing you need to make room for in your rapidly expanding suitcase! For dinner tonight, if you want to switch it up from Japanese, there’s est for French back at Otemachi, Spice Lab for Indian with Japanese sensibility, or Issei Yuasa for omakase-style Italian. 

This morning, wake up for one final breakfast at Otemachi, perhaps taking advantage of the Four Seasons app to have your dream spread delivered to your suite seamlessly. Upon checkout, your guide will ensure you have your printed ticket for the Shinkansen; depending on your specifications, luggage can be sent directly to Kyoto via a charter service, or you can carry it on the train.

Soak up the wonder of Tokyo Station, collecting as many snacks as your heart desires. The Shinkansen is more than just a means of transport, but part of the experience—marvel in its efficiency and reliability, compared to so many other train infrastructures around the world. Upon arrival at Kyoto Station, greeters will be on the platform to lend you a hand; you’ll need your printed train ticket to exit the station.

From the station, you’ll head directly to your shabu shabu lunch at Kyoto Hyoto Kyoto Ekimae Honten. This hotpot-style meal is equal parts fun and delicious; be sure you’re prepared to leave your shoes at the door. Directly following lunch, it’s time to recenter with a Zen tea ritual at a tea master’s home who has practiced under Buddhist monks. This serene experience will set the tone for the remainder of your time in the “City of a Thousand Shrines”—naturally, directly following the matcha, you’ll do a temple walk through the quiet grounds of Daitokuji.

It’s now time to check into Four Seasons Hotel Kyoto, a property just outside the city center that was built on an 800-year-old garden. If you’re up for more tea, the hotel has its own tea house in the middle of the garden. For dinner tonight, choose between staying on property and sampling the offering at Brasserie for French fare, Sushi Wakon for Edomae-style sushi at one of ten seats, or going into town for Kikunoi Honten for a proper Kyoto kaiseki moment. 

Today, your Japan itinerary is all about Kyoto at its most immersive. Your SmartFlyer travel advisor has worked with our local partners to privatize a Goma fire ritual. Set amidst Ninna-ji Temple, head temple of the Omuro School of Shingon Buddhism, monks will lead you through a sensory ceremony meant to purify energies and fulfill wishes you’ll write on wood to be burned. From there, monks will take you to areas of the temple normally not open to the public.

After this spiritual experience, the late morning is yours to customize. If you’re keen to see the bamboo forest you’ve seen so many photos of, your guide can take you to Arashiyma Bamboo Grove, a stop that pairs perfectly with Okochi Sanso Villa. If in the area, we adore Pottery Tanuki for their frog figurines, each handmade by the owner. Alternatively, if you want more off-the-beaten-path, you’ll head to Adashino Nenbutsuji Temple to see thousands of statues, plus bamboo groves without the crowds.

For lunch, we recommend a reservation at PIZZERIA MAMA. Japan’s knack for pizza is widely known, and this is some of the best. Afterward, opt for some arts and culture, either with a kintsugi workshop at POJ Studio, or a visit to teamLab Biovortex Kyoto. Depending on how much energy you have afterward, either head back to the hotel or do some wandering through Gion. For dinner, Hikiniku to Come is beloved for its charcoal-grilled wagyu beef patties served with rice and sauces.

Your final full day in Kyoto has been designed with flexibility in mind. A unique offering when staying at Four Seasons is the VIP Fushimi Inari walk, which starts right from the property. You’ll be led by the hotel team along a leisurely two-hour nature walk, ultimately leading you to a lesser-accessed back entrance of this key Kyoto attraction. Wander through the iconic orange arches, sure to get that quintessential photo. Your SmartFlyer travel advisor can help arrange for a car back to the hotel, where you can freshen up for the rest of the day.

This afternoon is all about intentionally unscheduled time. Take the chance to walk along the river and immerse yourself in the slower pace of Kyoto. For shopping, Kyoto is known for ceramics, with Tearoom Toka and The Terminal each having fabulous selections. If still on the hunt for denim, we love MOMOTARO JEANS, Japan Blue Jeans, and Ordinary Fits. Kyukyodo is your go-to for stationery. Head back to the property to change for dinner—tonight will be a memorable one. You’re slated to witness the finest form of Japanese entertainment with a private geisha dinner, paired with a sukiyaki menu. Not only will you witness their dance and musical performance up close, but you’ll enjoy their company, even getting the chance to play a traditional game.

This morning, it’s time to bid farewell to Kyoto. Luxuriate in one last breakfast at the Four Seasons Hotel Kyoto (don’t miss the black sesame paste on a pastry!) before meeting your transfer driver. The drive to Osaka is brief, and in less than an hour, you’ll be at Osaka Castle; this stop makes for the perfect transition during your Japan itinerary into this dynamic city. For lunch, your driver will bring you to Kitashinchi Hondori Tsuru Tontan Kinshoro where you’ll be able to pick out a bowl of udon bigger than your head—best enjoyed sitting on the floor, shoeless, of course. 

From the Castle, it’s off to Four Seasons Hotel Osaka, a contemporary counterpart to Kyoto’s heritage setting. Immediately upon walking in, it’s clear that this sleek property is in a class all its own. Depending on your preferences, your SmartFlyer travel advisor can arrange for you to be on the 28th floor of the hotel, which ultimately acts as a hotel within a hotel, offering ryokan-style rooms. Alternatively, you can settle into a more modern suite, all overlooking the sweeping city views. 

For dinner, we think the best way to dive right into Osaka is by taking a food tour. Led by a knowledgeable foodie guide, you’ll move between neighborhood favorites and lesser-known gems, weaving through the neon-lit streets of Dotonbori and tucked-away alleys you’d likely never find on your own. Expect a progressive tasting—think sizzling takoyaki, perfectly crisp kushikatsu, and regional specialties that paint the picture of why Osaka is called “Japan’s kitchen.” If you’re really feeling up for some fun, end the night with some karaoke in one of the city’s many spots catering to this beloved Japanese tradition.

This morning, start your day at your leisure. If you’re staying on the 28th floor, you’ll have access to the special Japanese breakfast room, serving—you guessed it—an authentic Japanese breakfast. If you’re in the mood for pampering, the 36th-floor spa at Four Seasons Hotel Osaka is an oasis of calm; be sure to soak up Japanese tradition by going into the ofuro and sauna.

From here, where your Japan itinerary takes you next is up to your mood. If you’re craving more shopping, consider strolling through Nakazakicho, where indie designers, vintage spots, and tucked-away cafés create a contrast to what you experienced with last night’s neon-colored backdrop. If you’re in town during the month of March, securing tickets to a sumo tournament makes for the ultimate cultural experience; we were fortunate enough to attend on our recent scouting trip, and it was a trip highlight. If sumo is of interest but you’re in town during other parts of the year, access to training stables is also an option.

Come evening, return to the Four Seasons Hotel Osaka to wind down. Whether you opt for a drink on property before going out, or wish to dine at the hotel, you’ve got plenty of options. The hotel’s Cantonese restaurant Jiang Nan Chun makes for a nice switch-up of cuisine at this stage in your Japan itinerary. 

Wake up knowing you’re headed back to Tokyo via high-speed rail. Check out of Four Seasons Hotel Osaka and head to the train station for your Shinkansen journey back to Tokyo Station. From there, a team member from Four Seasons Hotel Tokyo at Marunouchi will be awaiting you on the platform for the brief journey back to this recently renovated hotel. With just fifty-seven rooms, it’s a decidedly intimate note to end your Japan itineary on. 

Spend your final afternoon revisiting the neighborhoods you loved most, shops you couldn’t get enough of, and inevitably, a matcha spot left unvisited. Wrap this dream trip with dinner at Nagatacho Ohka Private Restaurant, a special occasion spot where everything is made to your personal preferences. Reservations are only made on a referral basis, but good thing you know someone. 

Wake up for one final Four Seasons breakfast before bidding Japan goodbye. Or rather, “see you later,” as this country has a way of leaving an imprint on its visitors’ hearts.