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Day
CityTravel / Notes
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Wednesday, May 20Early sleep; Fly into HND or NRT
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Thursday, May 21Tokyo (Shinjuku) (land in the afternoon)Arrive in Tokyo; transfer to hotel; drop bagsDays for jet lag buffer
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Friday, May 22Tokyo (Harajuku/Shibuya)
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MorningMeiji Jingu (go early, it’s calmer)
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Harajuku: Takeshita (quick look) + Cat Street drift
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AfternoonBlue Bottle Aoyama
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Omotesando architecture stroll + shops
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EveningShibuya Crossing + Hachiko
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Optional: Shibuya Sky (do it this night or Sat—whichever has the best weather)
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Saturday, May 23Tokyo (Shibuya/Daikanyama)Toyosu Fish Market; Meiji Shrine (Harajuku)
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Shibuya shopping: Shibuya 109, Loft, Tokyu Hands; Cat StreetTokyo → Kyoto (~2.5 hrs)
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Shibuya Sky observation deck
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Sunday, May 24Tokyo (Asakusa/Akihabara/Ginza)Senso-ji Temple (Asakusa)
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Nakamise Street for souvenirs; Sumida River Walk; Akihabara district
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Explore Ginza district
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Monday, May 25Tokyo (Ueno/Ikebukuro/Ginza)teamLab Borderless (Odaiba) OR Tokyo National Museum (Ueno)
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Ueno Ameya-Yokocho market; optional Ikebukuro visit: Sunshine City and Otome Road; Tokyo Giants Store
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Shopping in Ginza; visit Daikanyama
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DayCityPlan
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Tuesday, May 26Tokyo1Tokyo
Arrive in Tokyo; hotel check-in; short neighborhood walk; convenience store food; early dinner; early sleep
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2Tokyo
Jet lag buffer day; casual neighborhood exploring; coffee shops; Harajuku stroll; light shopping; early night
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3Tokyo
Meiji Shrine; Harajuku; Omotesando; Shibuya Crossing; Shibuya Sky at sunset; dinner in Shibuya/Ebisu
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4Tokyo
Asakusa & Senso-ji; Sumida River walk; Akihabara; evening in Ginza or Roppongi
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Wednesday, May 27TOKYO TO KYOTO (Central/Gion)Checkout; Shinkansen Tokyo → Kyoto5Kyoto
Shinkansen Tokyo to Kyoto; hotel check-in; Gion stroll; dinner in Pontocho Alley
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Nishiki Market for local goods6Kyoto
Fushimi Inari (early); Kiyomizu-dera; Sannenzaka & Ninenzaka; tea break; relaxed evening
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Gion district stroll; Pontocho Alley7Kyoto
Arashiyama Bamboo Grove; Tenryu-ji; Okochi Sanso Villa; optional monkey park; quiet night
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8Kyoto
Kinkaku-ji; Ryoan-ji; Ninna-ji; evening onsen or massage
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Thursday, May 28Kyoto (Higashiyama)Fushimi Inari Taisha9Kyoto
Flex day: Nara day trip OR Philosopher’s Path OR Nishiki Market OR cultural class
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Kiyomizu-dera Temple
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Evening stroll in Higashiyama
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Friday, May 29Kyoto (Arashiyama)Arashiyama Bamboo Grove
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Okochi Sanso Garden
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Final Kyoto stroll
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Saturday, May 30Kyoto to osakaCheckout; Train Kyoto → Osaka
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Dotonbori street walking; Shinsaibashi shopping
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Evening stroll in Namba
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Sunday, May 31Osaka (Namba/Dotonbori/Shinsaibashi)
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12Osaka
Day trip option: Hiroshima & Miyajima OR Kobe OR Universal Studios Japan
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Monday, June 1Osaka (Umeda/Kuromon/Shinsekai)
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Kuromon Market exploration13Osaka
Free day; shopping; revisit favorite areas; pack
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Shinsekai area walk14Osaka
Fly home from Kansai International Airport (KIX)
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Evening at Umeda Sky Building
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Kyoto → Osaka (15–30 min)
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Tuesday, June 2Osaka (fly out)10Osaka
Travel Kyoto to Osaka; hotel check-in; Dotonbori; street food crawl
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Checkout; Train to Kansai Airport11Osaka
Osaka Castle; Kuromon Market; Shinsekai; Umeda Sky Building at night
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Fly home
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THINGS WE KNOW WE WANT TO SEE/DO
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TOKYO
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KYOTO
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OSAKA
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Retro arcade neighborhood
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GENERAL
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fish market
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