Day 1 – Arrival: Roppongi & Ebisu
Arrive in Tokyo: Take direct airport train to Roppongi (express train direct into centre for subway connections)
Recommend staying in the Roppongi area i.e. APA hotel with views of Tokyo Tower
Afternoon: Stroll around Roppongi Hills and Tokyo Midtown
Coffee stop at Commons
Highballs at Just a Coffee Bar
Evening in Ebisu: Yakitori & natural wine at Wine Stand Waltz
Day 2 – Shibuya, Harajuku & Shinjuku
Morning: Breakfast at Bricolage Bread & Co.
Walk to Shibuya Scramble Crossing & Hachiko Square - capture the iconic crossing photos
TIP: Head to the Starbucks and view the chaos of the crossing from above
Afternoon: Embrace the streets and walk to Takeshita Street (Harajuku) – try street pancakes
Visit Meiji Jingu Shrine
Evening in Shinjuku: Explore city at night (3D cat billboard, Godzilla head)
Dinner at Omoide Yokocho – try Kameya Udon
Drinks in Golden Gai – tiny bars with lots of character
Day 3 – Parks, Skytree & Asakusa
Morning: Breakfast at Little Darling Coffee Roasters
Scenic walk through Aoyama Cemetery
Visit Ueno Park (museums, shrines)
Afternoon: Head to Tokyo Skytree (recommend pre-booking tickets)
Walk to Senso-ji Temple via Nakamise Dori
Street food stops: try Asakusa Chicken & 7-Eleven strawberry sandwiches
Evening: Small plates & sake tasting at Eureka!
Drinks & vinyl at Bar Martha – Guinness or Sapporo on tap
Day 4 – Culture, Shrines & Final Tokyo Night
Morning: Coffee at Blue Bottle (Roppongi) and vsit Tokyo Art Centre
Walk to Imperial Palace grounds
Refresh with drinks from one of the many vending machines dotted around the City
Loop back via Hie Shrine (photo-worthy stop with red Torii gates)
Evening: Dinner at Udon Shin (expect a queue but it’s worth it!)
Cocktails at SG Club (one of Asia's top bars)
End at a traditional listening bar like Grandfather’s
Day 5 – Coastal Escape to Atami
Morning: stock up on snacks at 7-Eleven and take the Shinkansen to Atami: Sit on the right side for Mount Fuji views
On arrival check in to a traditional homestay
Afternoon: Explore Atami Beach
Lunch at a local ramen spot (e.g., Ishin)
Stop for a glass of wine/champagne at Enoteca Maniffur
Walk the Natural Spring Trail around town
Relax in an Onsen (hot spring)
Evening: Dinner & local brews at Atami Craft Beer House
Early night to unwind
Day 6 – Atami Castle & Arrival in Kyoto
Morning: Enjoy homestay breakfast
Take the cable car up to Atami Castle for coastal views
Midday: Catch the Shinkansen to Kyoto arrive late afternoon and settle in
Take an Uber or public transport to Fushimi Inari Taisha – explore the famous red torii gates at dusk and miss the crowds
Dinner nearby: Ichiban Fushimiinari Ekimae (yakitori)
Train back to Kyoto Station and view Kyoto Tower at night
Optional: Late-night yakitori & Sapporo at Sukiyanen
Day 7 – Temples, Markets & Gion Nightlife
Morning: Coffee & cheese toastie at SOT
Early stroll around Kiyomizu-dera Temple (UNESCO site)
Walk via Higashiyama Ward, through Ninenzaka & Sannenzaka Hills
Matcha break at a traditional tea house
Afternoon lunch at Taku Sando Kyoto – try the chicken and egg sandos
Explore Nishiki Market – local snacks & shops
Evening sunset drinks at Inn the Moon Rooftop Bar
Dinner at Gion Yuki – small plates & sake in a traditional izakaya
Nightcap at Bar Mitchell – vinyl listening bar
Day 8 – Bamboo Forest, Tofu Tasting & River Walk (Arashiyama → Kyoto)
Morning Train to Arashiyama and Matcha break before entering the Bamboo Forest And walk the iconic grove paths under towering bamboo
Lunch: Shōrian – Unique 8-course tofu tasting menu (booking recommended)
Afternoon scenic walk back to central Kyoto along the Katsura River
Evening: Dinner at 66Tantan – local dan dan noodles and beers at Kirin City Beer Hall (Shinkyogoku area)
Day 9 – Osaka: Pancakes, Culture & City Lights
Morning: Take a 25-minute train from Kyoto to Osaka
Famous fluffy soufflé pancakes for breakfast at Elk
Midday stroll through bustling local streets and browse ceramic stores, independent and clothes stores
Matcha + toasted mochi at WAD Café (stylish and serene)
Afternoon: visit Osaka Castle – explore the grounds and soak in some culture
Early evening walk along Dōtonbori River with bright lights and buzzing vibes
Evening: street yakitori and local shopping in Dōtonbori area
Final nightcap: Milk Bar Listening Record Bar – vinyl, chill, drinks