Hey all, long time lurker. Finally returning to Japan after 10 years and bringing a buddy of mine for his first time. I’ve been working on this general itinerary over the last few days and was hoping for thoughts on the pace of the days (mostly Tokyo) and also if I am clearly missing something must-see or experience! Thanks for your help!
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🇯🇵 Japan Trip Itinerary (Sept 14–29, 2025)
✈️ Sept 14 (Sun) – Travel Day
• Depart JFK → Arrive Haneda (Tokyo)
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🗼 Tokyo (Sept 15–22)
Sept 15 (Mon) – Arrival / Orientation
• Check into Airbnb (Setagaya)
• Light neighborhood exploration + dinner nearby
Sept 16 (Tue) – Shibuya / Harajuku
• Meiji Shrine
• Takeshita Street (Harajuku)
• Omotesando (architecture + shopping)
• Shibuya Crossing & Scramble Square view
• Dinner: Shibuya or Ebisu Yokocho (izakaya alley)
Sept 17 (Wed) – Shimokitazawa / Kichijoji (+ Koenji optional)
• Shimokitazawa: coffee, thrift shops, art galleries
• Kichijoji: Inokashira Park, Harmonica Yokocho
• Optional evening in Koenji (izakayas + live music)
Sept 18 (Thu) – Toyosu / Odaiba (Koto-ku day)
• Toyosu Fish Market (tuna auction, breakfast sushi)
• TeamLab Planets
• (AFTERNOON STILL EMPTY) – Roppongi?
Sept 19 (Fri) – Imperial Palace / Akihabara / Kagurazaka
• Imperial Palace East Gardens + Nijubashi Bridge
• Tokyo Station (Ramen Street, Kitte rooftop)
• Akihabara: retro gaming, arcades, anime shops
• Evening in Kagurazaka (shrines, cobblestone alleys, dinner)
Sept 20 (Sat) – Asakusa / Ueno / Yanaka
• Asakusa: Senso-ji Temple + Nakamise Street
• Ueno: park + museum options
• Yanaka: old-town charm + traditional shops
• Evening: Sumo dinner show in Asakusa (8pm reservation)
Sept 21 (Sun) – Flex Day (options)
• Possible Roppongi (Mori Art Museum + Tokyo City View)
• Ginza (shopping + Kabukiza Theatre)
• Nakameguro / Daikanyama / Ebisu (cafés, river walk, izakaya crawl)
Sept 22 (Mon) – Travel to Osaka
• Check out by 11am, take shinkansen to Osaka
• Check into hotel (Namba area)
• Light evening walk / explore Dotonbori
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🏯 Osaka (Sept 22–29)
Sept 23 (Tue) – Osaka Core
• Osaka Castle
• Shinsaibashi & Dotonbori shopping/eats
• Dinner: Tonkatsu Katsu Hana (saved spot)
Sept 24 (Wed) – Osaka Attractions
• Osaka Aquarium Kaiyukan (saved spot)
• Umeda Sky Building (city views)
• Namba Yasaka Shrine
Sept 25 (Thu) – Day Trip to Nara
• Todaiji Temple + Big Buddha
• Nara Deer Park
• Kasuga Taisha Shrine
• Evening return to Osaka
Sept 26 (Fri) – Kobe (Day Trip option)
• Chinatown (Nankinmachi)
• Kobe beef lunch/dinner
• Kobe Harborland & Meriken Park waterfront
Sept 27 (Sat) – Kyoto (Day Trip option)
• Fushimi Inari Shrine (gates)
• Kiyomizudera Temple
• Gion District walk
Sept 28 (Sun) – Osaka Free Day
• Shopping, neighborhoods, or relax before departure
• Optional A-PIT Autobacs (saved spot)
Sept 29 (Mon) – Departure
• Flight back to USA
by Aggressive_Lack_3934