Itinerary Check: 21 days in Japan in May 2025 (Osaka, Kyoto, Tokyo) for husband’s surprise 30th birthday trip


I've tried to do a fair amount of research and come up with an itinerary that I think works well based on locations for everything. I’m planning this trip for my husband and I to surprise my husband for his 30th birthday, so I’m not really able to get his advice on this trip, so I’m looking for reddit to help me out!

Some things about us:

  • Our budget for this trip is around $12,000 (excludes any major shopping purchases)
  • We are big foodies, but know that nailing down food places can be tough given long lines
  • We want to experience all that Japan has to offer but also don’t want to lose out on actually ‘experiencing’ Japan because we’re going too fast
  • We don’t really care about the club scene but we’re potentially interested in renting a karaoke room
  • We love coffee so a cute coffee shop would be amazing to find!
  • I want to buy a luxury watch and/or luxury bag while we are in Japan during one of our shopping days

Things I need help with:

  • Where we should stay in each place. For example I’ve heard the Ginza district is an amazing place to stay, but there are so many choices in Tokyo. I also am unsure if we should splurge for places with a good view in the room or just focus on location. We’ve also discussed staying on property when going to Disney but I’m not sure if this is worth it.
  • I would love perspective on whether this itinerary is too aggressive
  • Please please please help me with restaurant ideas – I think I’m just overwhelmed by the sheer choices
    • I did put some meals in my listing below but I’m not married to the dates or places I listed below– I just wanted to have a list of high recommendation restaurants in my itinerary!
    • We want to try all the typical foods tourists want to try: waygu, sushi, ramen, gyoza, tonkatsu, udon, etc.
  • If we’re missing anything in our itinerary, let us know! Additionally if there are any items we should be considering when securing reservations for the activities I’ve listed below, please let me know!
  • Will laundry be an issue for us given the duration of our stay? Should we pack enough for the trip or plan to do laundry during our trip?

Day 1: Friday, May 9, 2025 (Tokyo)

–        Flight from ORD to HND (Arrival time estimated 3:30 PM the next day)

*** Note: I have been banking my points to fly us business class to Tokyo so while the flight will be overnight, I am hoping we’ll be more rested)

Day 2: Saturday, May 10, 2025 (Tokyo)

–        Arrive at HND (mid-afternoon)

–        Taxi to hotel

–        Arrive to Hotel (Hotel TBD)

–        Shinjuku Kabukicho & Golden Gai Walking Tour (6 – 8 PM)

Day 3: Sunday, May 11, 2025 (Tokyo)

–        Sightseeing/Shopping Day

  • Rainbow Bridge
  • Shibuya Scramble Crossing
  • Toho Cinemas Shinjuku
  • Akihabara
  • 7-Eleven
  • MEGA Don Quijote
  • Pokemon Center Mega Tokyo

–        Eat McDonald’s in Shibuya (this is a tradition for my husband and I to eat at a McDonald’s in every new country)

–        Rooftop Bar Experience – Andaz Toranomon Hills

–        Meal: A Happy Pancake Omotesando

Day 4: Monday, May 12, 2025 (Tokyo)

–        Shibuya Sky

–        Studio Ghibli Museum (I know that tickets for this can be tough to obtain, so I have a plan to have multiple people help me to secure tickets to this event)

–        Tokyo Metropoliton Gov’t Building

–        Tokyo Dome (Baseball Game)

–        Meal: Wagyu Yakiniku Panga

Day 5: Tuesday, May 13, 2025 (Tokyo)

–        Tsukiji Outer Market

–        teamLab Planets Tokyo

–        Sumo Wrestling Tournament Viewing (we don’t plan to watch the entire days’ worth of tournaments)

–        Street Kart Tokyo Bay

–        Meal: Uobei

Day 6: Wednesday, May 14, 2025 (Tokyo)

–        Shrine Day

  • Senso-ji
  • The East Gardens of the Imperial Palace
  • Kikyo-mon Gate
  • Meiji Jingu
  • Togo Shrine

–        Harajuku Station

–        Mt. Fuju Helicopter Tour

–        Travel to Disney Hotel – Planning to stay at Tokyo DisneySea Hotel MiraCosta

–        Meal: Kirby Cafe

Day 7: Thursday, May 15, 2025 (Tokyo)

–        Disney Sea Day (We plan on paying for Premier Access to avoid long lines)

Day 8: Friday, May 16, 2025 (Tokyo)

–        Tokyo Disneyland Day (We plan on paying for Premier Access to avoid long lines)

Day 9: Saturday, May 17, 2025 (Tokyo)

–        Check Out of Tokyo DisneySea Hotel MiraCosta

–        Train to Osaka (anticipate arriving early afternoon)

–        General Sightseeing (Please provide any good suggestions for a half day of sightseeing!)

  • Osaka Castle
  • Shinsaibashi Market

–        Meal: Katsudon Chiyomatsu

–        Meal: Ichiran Ramen

Day 10: Sunday, May 18, 2025 (Osaka)

–        Shrine Day

  • Namba Yasaka Jinja
  • Shitenno-Ji
  • Hozenji
  • Sumiyoshi Taisha

–        Dotonbori District

–        Sightseeing

–        Meal: Rikuro’s Namba Main Branch (Rikuro’s Cheesecake)

–        Meal: Gyukatsu Motomura

Day 11: Monday, May 19, 2025 (Osaka)

–       Universal Studios Japan

Day 12: Tuesday, May 20, 2025 (Osaka –> Hiroshima)

–        Day Trip to Hiroshima

–        Note: I’ve thought about potentially staying on Miyajima Island the day we went to Hiroshima but wasn’t sure if this was worth it and if so, if I should lose one of my Tokyo days on the backend.

Day 13: Wednesday, May 21, 2025 (Kyoto)

–        Travel to Kyoto

–        Nishiki Market

–        Kimono Tea Ceremony with Geisha

–        Pontcho Kaburenjo Theatre Show

–        Gion Sightseeing

Day 14: Thursday, May 22, 2025 (Kyoto –> Nara)

–        Day trip to Nara

  • Nara Park
  • Eat at Okaru (Japanese pancakes)
  • Todai Ji Shrine

Day 15: Friday, May 23, 2025 (Kyoto)

–        Shrine/Temple Day

o   To-ji Gojunoto (5 Story Pagoda)

o   Fushimi Inari Taisha

o   Shimogamo-jinja Shrine

o   Higashiyama Jisho-Ji

o   Honen-in Temple

–        Meal: Kichi Kichi Omurice

 

Day 16: Saturday, May 24, 2025 (Kyoto)

–        Shrine/Temple Day

  • Nijo Castle
  • Kiyomizu-dera

–        Shopping: glänta Kyoto Sanjo Kawaramachi (custom rings)

–        Shopping: Ghibli Store

–        Shopping: Custom chopsticks

–        Meal: Gyoza Hohei

Day 17: Sunday, May 25, 2025 (Kyoto)

–        Shrine/Temple Day

  • Kinkaku-Ji
  • Ryoan-Ji

–        Shopping: Kikuichimonji

Day 18: Monday, May 26, 2025 (Kyoto –> Hakone)

–        Train to Hakone

–        The Hakone Open-Air Museum

–        Stay in a Ryokan in Hakone (My top pick is Spa Resort Ryokan Hakone Ginyu)

Day 19: Tuesday, May 27, 2025 (Hakone –> Tokyo)

–        Train to Tokyo

–        Wrap up anything we missed

  • Adaibo beach?
  • HEAD SPA Kuu
  • I’m donut! donuts

–        Stay in a capsule hotel

Day 20: Wednesday, May 28, 2025 (Tokyo)

–        Final Shopping Day in Tokyo

–        Meal: Pokemon Cafe

–        Meal: Nihonbashi Kaisen Donburi Tsujihan Nihonbashi

Day 21: Thursday, May 29, 2025 (Tokyo)

–        Fly home

  • Unfortunately, we likely won’t have enough points to fly back in business class

–        This is my husband’s actual birthday, so ideas on how to make this special before our flight, let me know!

by Individual_War9075

Leave a Reply
You May Also Like