A Two-Week Curated Journey Through Japan: Tokyo, Niseko, and Kyoto

Designed for travelers seeking a blend of modern vibrance, mountain retreat, and cultural immersion, this two-week journey through Japan showcases the country through a polished lens. From the high-energy neighborhoods of Tokyo to the powder slopes of Niseko and the serene temples of Kyoto, this trip balances discovery, downtime, and design.

This is Japan at its most intentional: fast-paced but never frantic, rooted in tradition yet endlessly inventive. Whether you're traveling as a family, couple, or solo with friends, this journey gives you a soft landing into Japanese culture—with enough structure to relax and enough freedom to explore.

Days 1-3 in Tokyo: Shibuya, Subculture & Jazz Bars

Day 1: Your journey begins in the heart of Shibuya with panoramic skyline views from a central Tokyo hotel. Spend your first night wandering through retro backstreets, easing into the city with a visit to Nonbei Yokocho for postwar-era izakayas and nearby jazz bars like Pres Jazz or Music Bar 45. Explore: Shibuya Crossing, Daikanyama design boutiques, and Kuramae craft stores

Day 2: Take a guided tour or self-led circuit through Omotesandō, Asakusa, or Harajuku. Wind down with a curated whiskey or sake tasting.

Day 3: Follow your own interests: knife forging, sumo practice, manga museums, or a custom design loop through Nezu Museum and Ginza's Itoya.

Pro Tip: Tokyo's jazz scene is globally underrated. Choose a standing bar for an immersive sound experience

Don’t Miss: A cocktail at the Park Hyatt’s New York Bar at golden hour — with iconic skyline views and potential glimpses of Mt. Fuji.

Days 4-6 in Niseko: Powder, Onsen, and Mountain Refinement

Day 4: Fly north to Hokkaido and check into Higashiyama Niseko Village, a Ritz-Carlton Reserve. This ski-in, ski-out sanctuary offers pristine slopes, refined dining, and serene onsen culture.

Day 5: Full day on the slopes, sake tastings, fireside drinks

Pro Tip: Arrive early enough to fit in a few afternoon runs and an onsen soak before dinner.

Don’t Miss: A post-ski onsen soak as snow falls — one of Japan’s most restorative and culturally iconic winter experiences.

Days 6-9 in Kyoto: Temples, Markets & Teahouses

Day 6: Trade mountains for moss gardens as you journey to Kyoto, Japan’s cultural soul. Stay at the Hilton Kyoto near Gion and Kawaramachi, perfect for blending historic charm and modern energy. Arrive late, unwind with a stroll or light local meal

Day 7: Private guided day tour of Fushimi Inari, Arashiyama Bamboo Grove, and Kinkaku-ji

Day 8: Self-led morning—kimono class, Nishiki Market, or a tea ceremony—then evening in Gion or Pontocho

Pro Tip: For fewer crowds, visit Fushimi Inari or Arashiyama as early as possible

Don’t Miss: Wandering the lantern-lit alleyways of Pontocho after dinner — the essence of Kyoto charm and old-world allure.

Days 9-12 in Tokyo Redux: Markets, Denim and Culture

Day 9: Return to Tokyo for the finale. Base yourself at the Hyatt Regency in Shinjuku, close to the race start and Tokyo’s funkier, more local layers.

Day 10: Visit Toyosu Fish Market at dawn, then shop for artisanal selvedge denim in Koenji, Kuramae, or Shimokitazawa

Day 11: Support or participate in the Tokyo Marathon, followed by a celebratory dinner and jazz set

Day 12: Morning departure or one final walk through Yoyogi Park

Pro Tip: This is your moment to lean into hyper-local experiences. Skip the major attractions and explore Tokyo’s quieter, cooler side.

Don’t Miss: Shopping for Japanese denim in Koenji or Shimokitazawa — the perfect Tokyo souvenir with story, style, and legacy.

Japan Through Journey Quick FAQs

Is this trip family-friendly? 

Yes, with cultural, culinary, and ski elements for all ages

Best time to visit Japan?

February for powder skiing and early cherry blossoms in Kyoto

Do I need to speak Japanese? 

Not essential, but key phrases are helpful. Most hotels and guides speak English.