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Japan Essentials: A 14-Day Cultural Escape from Tokyo to Kyoto

Plan Your Bespoke Journey
  • From July 2025
  • 14 days
  • Tokyo, Nagano, Kyoto & Beyond

From private geisha dinners in Kyoto to design hotels beside Mt Fuji, this two-week experience combines Japan’s must-see highlights with rare encounters.

Week One

Days 1-5: Tokyo

Arrive via private airport transfer and check-in to Aman Tokyo, one of the world’s most celebrated hotels, offering panoramic skyline views and a serene spa. Explore iconic landmarks and lesser-known neighbourhoods, beginning with a private tour of Meiji Shrine, where you’ll gain insight into Japan’s spiritual traditions and rituals. Wander through Tomigaya, a low-rise neighbourhood of Scandinavian cafes and independent design bookstores. Visit a sumo stable for an intimate look at the rituals behind Japan’s national sport. Sample fresh seafood and street-side sushi at the outer lanes of Tsukiji Market, and spend a morning at Daikanyama T-Site, a beautifully curated bookstore complex filled with art volumes, travel guides, and Japanese design publications.

Days 5-6: Lake Kawaguchiko

Just two hours from Tokyo, the Fuji Five Lakes region offers a slower pace and direct connection to nature. Stay at Hoshinoya Fuji, a minimalist retreat set in the forest above Lake Kawaguchiko, where floor-to-ceiling windows offer uninterrupted views of Mt Fuji. Wake early for a sunrise canoeing experience on the lake, followed by a private cycling tour through hidden temples, and pathways rarely explored by visitors. Visit Fujiyoshida, a traditional town at the mountain’s base, and hike to Chureito Pagoda, where sweeping views frame Mt Fuji alongside the silhouette of a five-storey pagoda.

Asakusa, Tokyo — Step into old Tokyo at Senso-ji, the city’s oldest temple. Arrive early for crowd-free moments beneath lanterns and incense. A rare chance to see timeless Japan unfold in a district where centuries-old rituals still shape daily life.
Lake Kawaguchiko — Wake to misty views of Mt Fuji reflected in still water. Stay lakeside in a private onsen suite, explore fiery autumn tunnels, and capture the mountain’s beauty from hidden vantage points — a once-in-a-lifetime moment in Japan’s natural heart.
Gion Kyoto — Wander Kyoto’s most elegant geisha district at golden hour, past lantern-lit teahouses and silent alleyways. Join a private tea ceremony or catch a glimpse of a real geiko — a fleeting encounter with a world few truly experience.

Week Two

Day 6-8: Takayama & Nagano

Step back in time in Takayama, a preserved Edo-period town known for its wooden streets, morning markets, and signature Hida beef. From here, venture into the Japanese Alps to Kamikochi, a pristine valley of forests, rivers, and towering peaks. Cross the iconic Kappa Bridge and follow trails along the Azusa River, or take on longer hikes to dramatic alpine summits like Mt. Kita-Hotakadake.

Day 8-12: Kyoto

Wake up to panoramic city views from Banyan Tree Higashiyama Kyoto, a new hilltop retreat offering a rare perspective over Kyoto’s historic skyline. Begin in Gion, the city’s famed geisha district, where lantern-lit alleys and preserved machiya architecture evoke a sense of old Kyoto and enjoy an exclusive private geisha dinner in a traditional teahouse. Explore hidden temples and lesser-known bamboo groves in Arashiyama, followed by a private boat cruise through its forested riverside. Dive into Kyoto’s culinary scene with a private food tour through Nishiki Market, where generations of artisans sell handmade sweets, fresh seafood, and traditional ceramics.

Day 12–14: Naoshima

Your final stop is Naoshima, Japan’s island of contemporary art. Stay overnight at Benesse House, a museum-hotel designed by Tadao Ando where you can explore exhibits 24/7. See Yayoi Kusama’s Yellow Pumpkin, a now-iconic sculpture perched on the shore, and visit Naoshima Pavilion, a futuristic mesh structure by Sou Fujimoto. At the Valley Gallery, Kusama’s mirrored spheres and Ozawa’s modern Buddha statues line the approach to one of Ando’s newest masterpieces — a poetic blend of form, light, and land.

Sumo Stable Visit, Tokyo – Step inside a real sumo stable for an intimate glimpse into Japan’s national sport. Observe morning training sessions, learn about the wrestlers’ rigorous lifestyle, and witness the traditions that shape sumo’s cultural legacy.
Traditional Tea Ceremony, Kyoto – Participate in a private tea ceremony in a historic Kyoto teahouse. Learn the mindful rituals of preparation and presentation from a tea master while surrounded by seasonal wagashi sweets, tatami mats, and centuries-old calm.
Private Geisha Dinner, Kanazawa – Experience an evening of refined tradition with a one-on-one geiko performance in a Kanazawa teahouse. Enjoy seasonal kaiseki cuisine and quiet conversation in one of Japan’s most exclusive cultural settings.
Reviews

Ben has been invaluable in planning my family Japan trip! He has a keen sense for what you will enjoy and is excellent at tailoring his tips to specific tastes.

Lauren Born, California, USA

The session with Ben was extremely valuable. Making the most of our time and money is crucial for a trip to Japan, and this is a great way to ensure that happens.

Gene Desrochers
Aman Tokyo – Occupying the top floors of the Otemachi Tower, Aman Tokyo blends urban sophistication with ryokan calm. With panoramic city views, serene design, and a soaring light-filled spa, it’s a true retreat in the heart of the capital.
Hoshinoya Fuji – A luxury glamping resort nestled in forested hills overlooking Lake Kawaguchiko. Private cabins, outdoor fireplaces, and mountain air make this an atmospheric base for peaceful Fuji views and seasonal colours.
Banyan Tree Higashiyama Kyoto – Newly opened in the Higashiyama hills, this intimate retreat offers a modern take on Kyoto luxury — think elegant suites with cypress tubs, panoramic views, and close access to both temple paths and quiet neighbourhoods.
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