The Trendsetter
A punchy, high-style Japan escape for travelers chasing what’s next fashion, food, and futuristic vibes.
Cities in this Itinerary:
Tokyo, Osaka
Itinerary Overview:
6
Nights
Tokyo – 4 nights
Streetwear, nightlife, gallery-hopping, and cafes with playlists you’ve never heardOsaka – 2 nights Wild eats, underground music, and retro grit
Verified
Kabuk Hotels
In This Trip:
Recommended
Cultural Experiences:
Trend tour of Harajuku, Cat Street & Daikanyama with style guide
Custom cafe-hop or sneaker shop map in Shibuya + Shinjuku
Nightlife intro tour in Tokyo (non-touristy bars, record shops)
Bullet train to Osaka
Osaka street food crawl and photo walk
Day-by-Day
Journey
Day 1 — Arrival in Tokyo
Start with Tokyo’s pulse.
Arrival & Transfer: Land at Haneda or Narita and check in to lyf Shibuya Tokyo, a design-forward co-living space in the heart of youth culture.
Afternoon: Walk Shibuya Crossing, browse small concept shops, and explore Parco’s creative floors.
Evening: Dinner at a casual izakaya or ramen bar, then rooftop cocktails nearby.
Day 2 — Fashion & Subculture
Morning: Guided trend tour through Harajuku, Cat Street, and Omotesando — see how local designers reinterpret global streetwear.
Afternoon: Explore Daikanyama’s boutique district and visit a curated gallery or bookstore café.
Evening: Try an omakase burger or modern izakaya dinner in Shibuya; optional nightlife intro tour (record bars or live DJ set).
Day 3 — Café-Hopping & Sneaker Maps
Morning: Custom café-hop through Shibuya and Shinjuku — minimal interiors, latte art, and playlists worth saving.
Afternoon: Visit Kappabashi or Akihabara for unique gadgets and creative accessories.
Evening: Free night — shop, rest, or catch an art-house film at a Tokyo cinema.
Day 4 — Art & Future Tokyo
Morning: Visit teamLab Planets or Mori Building Digital Art Museum for immersive installations.
Afternoon: Relax at Yoyogi Park or explore Nakameguro’s riverside cafés.
Dinner: Chef’s tasting or creative fusion restaurant, followed by a stroll through Ebisu’s night scene.
Day 5 — Tokyo → Osaka | Street Style to Street Food
Morning: Ride the Shinkansen to Osaka (~2.5 hrs).
Check-In: OMO7 Osaka by Hoshino Resorts, your vibrant base in Shinsekai.
Afternoon: Orientation walk through Dotonbori, snapping photos along the neon canal.
Dinner: Street food crawl — takoyaki, okonomiyaki, and kushikatsu.
Day 6 — Urban Cool in Osaka
Morning: Explore Amerikamura, the city’s creative and vintage fashion district.
Afternoon: Gallery-hop or take a street photography walk with a local guide.
Evening: Dinner in Namba or Shinsaibashi, with optional underground music stop.
Day 7 — Departure
Morning: Sleep in and grab coffee at a local café.
Transfer: Shinkansen or flight back to Tokyo or Kansai Airport for departure.
