2 Week Japan Itinerary: Tokyo, Osaka, Kyoto, and Hakone

Updated: October 2026

Pirate sightseeing ship on Lake Ashi with snow-capped Mount Fuji rising behind the hills — A Hakone pirate ship on Lake Ashi with Mount Fuji behind it.

This 2 week Japan itinerary took my daughter and me from the neon of Shinjuku to the onsens of Hakone, with stops in Osaka, Nara, and Kyoto along the way, and we never felt rushed. If you are still planning, start with Japlanning 101: Your Crash Course to an Epic Trip.

My daughter has a gluten allergy, so food took real planning. Gluten Free Tours Japan (GFT) suggested gluten friendly restaurants and cafes for each city, booked three of our hotels, and arranged our private arrival and departure transfers.

“GFT was hands on from the start. They had suggestions for every city, and when we could not find our rickshaw driver in Nara, they helped us track him down. My daughter got to enjoy the food in Japan instead of worrying about it.”
— Izzy

Here is how the rest of the trip broke down.

Day 1 · Arrival in Tokyo

Orange and blue sunset from a plane window with a mountain silhouette on the horizon — Sunset from the plane window on the way to Japan.

My daughter Christina landed first and took a private transfer to The Gate Hotel Asakusa Kaminarimon. While she waited for me, she walked Hoppy Street along the Sumida River and picked up dinner from Hinatomaru Sushi, a short walk from the hotel. I arrived close to midnight on a separate flight, and GFT arranged a private transfer for me as well. Christina had saved some of her sushi in the room fridge, so a late dinner was waiting for me.

Takeout tuna and salmon nigiri and salmon sashimi on a hotel room table with a suitcase in the background — Sushi from Hinatomaru for arrival.

Learning a few phrases before you land makes the first day easier, so see my Guide to Useful Japanese Words and Phrases.

Day 2 · Tokyo · Day One

Woman posing in front of the five-story red pagoda at Senso-ji Temple in Tokyo, with a man in traditional dress walking past — The five-story pagoda at Senso-ji Temple in Asakusa.

Asakusa set the pace for a slow morning. Matcha at Geisha Coffee came with a bonus: a 7-Eleven sits directly across the street, and its egg salad sandwich made an easy breakfast to go with it.

Nakamise-dori, the long shopping street in Asakusa, was worth a slow walk, and it is where Christina and I bought our lucky cats. The story behind them is in Lucky Cat Japan: The Story Behind Maneki-Neko. The street leads straight to Senso-ji Temple, the oldest Buddhist temple in Tokyo, where the five-story pagoda made an easy photo stop.

Kappabashi, known as the kitchenware capital of Tokyo, was the next stop. Near the main intersection, a custom manhole cover celebrates the Sarazanmai anime with kappa characters. It was the first decorative cover Christina and I spotted on the trip, and my Ultimate Guide to Decorative Manhole Covers in Japan explains the history and how to collect manhole cards.

Decorative manhole cover near Kappabashi in Tokyo with kappa characters from the Sarazanmai anime — The Sarazanmai manhole cover near Kappabashi.

Lunch was at T’s Kitchen, a good option for gluten free diners nearby. Ameyoko Market in Ueno, once an old black market street, filled the early afternoon.

Woman in a cream kimono kneeling on tatami beside an iron kettle and bamboo ladle during a tea ceremony in Tokyo — The tea ceremony at Maikoya in Asakusa.

The evening started with a tea ceremony at Maikoya, followed by dinner at Heijoen for yakiniku, wagyu, and Kobe beef, with gluten free options available. From there, the night moved through Akihabara, the electric town known for its neon, and into Shinjuku for the 3D cat billboard at Cross Shinjuku Vision. We closed the night with two bars, Bar Benfiddich in Shinjuku and New York Bar at the Park Hyatt. My Best Cocktail Bars in Tokyo: A Complete Guide covers both, along with Virtù at the Four Seasons.

Day 3 · Tokyo · Day Two

Tray of five tuna nigiri arranged in a flower shape with a yellow garnish in the center, from Maguroya Kurogin at the Tsukiji Outer Market — Tuna nigiri from Maguroya Kurogin at the Tsukiji Outer Market.

An early start at the Tsukiji Outer Market included a stop for fresh tuna sashimi and nigiri at Maguroya Kurogin, eaten at a small table with cups of green tea. From there, it was on to Onitsuka Tiger in Ginza, which opens at eleven and personalizes purchases with embroidery. Read Onitsuka Tiger in Japan: What to Know Before You Buy before you go.

While the shoes were being embroidered, we walked to Louis Vuitton, where Christina chose a passport cover and had it hot stamped. We ate at Le Café V on the seventh floor while we waited, then picked up the shoes and went back for the cover. The full story, from the hot stamping to the cafe, is in Louis Vuitton Ginza Tokyo: Passport Cover and Le Café V.

Woman standing beside a tree on a Ginza street with the colorful Louis Vuitton building behind her — Walking through Ginza toward the Louis Vuitton building.

The afternoon moved to Harajuku for Takeshita Street, then along Cat Street into Shibuya.

Capsule toy machines are everywhere in Japan, and Christina and I tried a few along the way that afternoon. My Ultimate Guide to Gachapon Capsule Toys in Japan explains how they work and what to look for.

Dinner was a kaiseki seafood reservation at Hoshino Naru Kai Aoyama, with gluten free options. Afterward, Christina and I headed back to Shibuya Crossing, which is at its best after dark with the lights and the crowds.

Day 4 · Tokyo to Osaka

White Shinkansen bullet train waiting at a station platform with a traveler and luggage standing nearby — The Shinkansen waiting at the platform.

A slow checkout morning included one more matcha at Hatoya. Luggage was sent ahead to the next hotel, which made the Shinkansen ride far easier. We used the same service for every move on the trip, and my Ultimate Guide to Luggage Transport in Japan explains how it works.

The Shinkansen to Osaka takes about two and a half hours, with a bento box lunch on board. If given the choice, take the right side of the train. The bento box deserves its own guide, so see Ekiben at Tokyo Station: The Ultimate Train Lunch Guide, and for tips on riding the train, read Train Etiquette in Japan: Everything You Need to Know Before You Ride.

Open Jojoen yakiniku bento box with grilled beef over rice and four small side dishes of kimchi and pickled vegetables — My Jojoen grilled meat bento on the Shinkansen to Osaka.

We checked into the St. Regis in Osaka’s Chuo Ward, where Christina and I watched the champagne sabrage on the twelfth floor before heading out. We spent the rest of the evening in Dotonbori under the neon lights, with dinner at Genji Soba, which has gluten free options.

Day 5 · Osaka · Day One

Woman standing on a gravel path in front of Osaka Castle with its green tiled roofs and gold tiger decorations. — Osaka Castle.

Morning coffee led into Shinsekai for the Tsutenkaku Tower, then Osaka Castle. Lunch was a gluten free option at Comeconoco, followed by an afternoon of secondhand designer shopping on Shinsaibashi Street.

Day 6 · Osaka & Nara Day Trip

A mother and daughter posing with friendly sika deer in Nara — My daughter and I with the free roaming deer in Nara.

The morning started with complimentary lattes ordered through room service, a perk of the St. Regis, before Christina and I caught a train from Osaka Namba to Kintetsu Nara Station.

In Nara, a rickshaw reservation was set to start at Kofukuji Temple, but Christina and I had trouble finding our driver, and GFT helped us locate the rickshaw. The free roaming deer were everywhere from there.

Todai-ji Temple houses a giant Buddha statue, Kasuga Taisha Shrine is lined with hundreds of stone lanterns, and Yoshikien Garden is a quieter stop nearby. Naramachi, the old wooden townhouse district, and Mochiidono Center Gai, an indoor shopping street, filled the rest of the afternoon, with a gluten free lunch option at Big Mountain Cafe. Look down while you explore, because Nara’s manhole cover features the city’s sika deer surrounded by camellia blossoms.

Decorative manhole cover in Nara showing sika deer surrounded by camellia blossoms — Nara’s manhole cover features the city’s sika deer.

The Kintetsu Rapid Express runs back to Osaka in under an hour. Dinner that night was a reservation at Sushi Takumi, a Michelin starred spot near the hotel.

Day 7 · Osaka to Kyoto

Staff holding a whole tuna on a cutting board during a tuna cutting demonstration at Nishiki Market in Kyoto — Watching a whole tuna being cut at Nishiki Market in Kyoto.

A spa morning at the hotel came first, then a half hour train to Kyoto, with our luggage sent ahead to the Hyatt Regency in Higashiyama. Nishiki Market, known as Kyoto’s kitchen, was the first stop downtown, and we stopped to watch a whole tuna being cut. My guide to Nishiki Market Kyoto: What to Eat and Where to Shop covers what to try. A return to the hotel to drop off purchases came before heading to Fushimi Inari Shrine in the early evening. Dinner was a teppanyaki reservation at Planca Ken.

Day 8 · Kyoto · Day One

Posing with three ninja mannequins beside the Samurai Ninja Museum Kyoto sign — The ninja mannequins outside the Samurai Ninja Museum in Kyoto.

A samurai experience reservation opened the morning, and I shared the full story in Samurai Ninja Museum Kyoto Experience: Stepping Into Japan’s Warrior History. Lunch and an afternoon at the Imperial Garden and Palace in Kamigyo followed. Nijo Castle and a stop at Le Labo rounded out the walk before heading back to the hotel. Read more about that stop in Explore Le Labo Kyoto: A Unique Blend of Design and Fragrance.

In the evening, a two hour reservation at teamLab BioVortex preceded dinner at Yakiniku Toraji.

Day 9 · Kyoto · Day Two

Two women riding in a rickshaw under a tall canopy of bamboo in the Arashiyama Bamboo Forest — A rickshaw ride through the Arashiyama Bamboo Forest.

Matcha at the hotel led into Arashiyama, where a rickshaw reservation through the Bamboo Forest set the tone for the morning. My Ultimate Guide to a Day in Arashiyama in Japan covers everything the area has to offer, including a Pokémon manhole cover near Togetsukyo Bridge.

Shopping, foot massages, and coffee at Arabica filled the rest of the day. Christina and I each bought a santoku knife at Yoshimune Knives Annex, and the Japanese Knife Guide: Types, Uses, and How to Choose explains what to look for.

Dinner was in Gion at Maru at Keika, a gluten free bar and restaurant. Uno Yukiko, known for its gluten free and vegan vending machine as well as a full restaurant menu, is nearby.

Day 10 · Kyoto · Day Three

Coffee at Here Kyoto started an early morning rickshaw reservation through Higashiyama, taking in Yasaka Shrine and Kiyomizu-dera Temple before local shopping along Sannenzaka and Ninenzaka streets. Koma Gallery Cafe had a gluten free snack option along the way.

The afternoon moved into Gion for the Yasaka Pagoda, small shops, and the chance to spot geisha. My Kyoto Geisha Guide: Geiko and Maiko Explained explains what you are seeing. Hashiya Kaede is a good stop for chopsticks, and you can learn how to use them properly in Chopstick Etiquette in Japan: Rules You Need to Know.

Pontocho, across the river from Gion, closed out the evening with dinner at Ponto Yakiniku Shin, which has gluten free options. Christina and I ended the night at Bee’s Knees, a cozy cocktail bar in Kyoto that is easy to walk past if you are not looking for it. I wrote more about it in Bee’s Knees Kyoto: A Cozy Cocktail Bar Worth Finding.

Day 11 · Kyoto to Hakone

A slow morning left room to circle back to anything missed in Kyoto before the two hour train to Hakone, with luggage sent ahead once more. We checked into Laforet Hakone Gora Yunosumika, a premiere room with an open air bath, and stopped at Nakafuku, a gluten free and vegan bakery near the train station, before settling into the onsen. Dinner was at Zen Sushi.

Day 12 · Hakone · Day One

Woman in a red hat sitting in a Hakone Ropeway photo booth with a Mount Fuji mural — The Hakone Ropeway photo spot.

A slow morning at the hotel led into a taxi to the Hakone ropeway, which climbs to Owakudani, the volcanic valley known for its black eggs. They turn black when boiled in the hot springs there. We tried one, and it tasted like an egg, but the mountain views made the stop worth it.

Hand holding a black egg in front of a shop at Owakudani in Hakone — A black egg at Owakudani, boiled in the volcanic hot springs.

After the ropeway, we rode a pirate ship across Lake Ashi, with Mount Fuji in view across the water. The evening was left open for the onsen, followed by dinner at Itoh by Nobu.

Day 13 · Hakone to Tokyo

Matcha at the hotel started the day, followed by the two hour train back to Tokyo and check in at Hotel Grandbach, a twin room. Lunch was an omakase reservation at Futabazushi, and the afternoon continued shopping in Ginza. Ginza sits in Tokyo’s Chuo Ward.

We ended the night with a nightcap at Virtù in the Four Seasons, where the team prepared gluten and dairy free nibbles for Christina without any fuss. I wrote more about the bar in my Best Cocktail Bars in Tokyo: A Complete Guide.

Gold lettering on a purple Virtù menu next to a glowing candle on a wooden table at the Four Seasons in Tokyo — Virtù at the Four Seasons in Tokyo.

Day 14 · Departure

A slow final morning with matcha and breakfast left plenty of time before the afternoon flight home.

Blue and pink Chuo Ward manhole cover with azalea blossoms beside a hand holding an iced matcha drink — Chuo Ward’s manhole cover in Ginza with an iced matcha.

Japan Close

Two weeks across four bases gave Christina and me time to slow down in each city instead of skimming the surface. We still talk about the small moments, like the sushi Christina saved in the room fridge for my midnight arrival and the pirate ship we rode across Lake Ashi with Mount Fuji in the distance. What I remember most is the patience and courtesy of the people we met along the way. Japan has stayed with me long after we got home.

If you are planning your own trip, these guides may help:

— izzy