Hey all! My wife and I are in the process of planning a 2 week family trip for us and our 2 teenage daughters. We're looking to go May 10-June 12, 2026. We're still in the early stages of the process but the thing we're struggling with the most is trying to build an itinerary. We are huge Disney fans and visiting the Disney parks while there is a bucket list item for us, we also want to stay on property while there. This, along with visiting other parts of Tokyo and traveling to Kyoto and Osaka, are our primary goals.

Since we don't have any experience with visiting Japan we've done a good bit of research and utilized ChatGPT to help us craft a potential itinerary. However, because we've never been before, we're not sure if this itinerary would work or if there are potential issues in it. We're hoping y'all can give this a look and let us know if this makes sense or if you have any suggestions on how to make this a more solid plan.

Day-by-day (Sat May 30 → Fri Jun 12, 2026)

Day 1 – Sat 5/30 – Arrive Tokyo (HND/NRT).

• At the airport, same-day luggage delivery to your Tokyo hotel (JAL ABC/Yamato counters) so you can ride the train hands-free. Check cutoffs; typical same-day hotel delivery is available for central Tokyo districts (paid per bag). Dinner near hotel, early night.  

Day 2 – Sun 5/31 – Tokyo (Asakusa → Akihabara or Ueno).

• Senso-ji & Nakamise shopping street, Sumida riverside stroll. Afternoon: Ueno Park museums or Akihabara arcades.

Day 3 – Mon 6/1 – Tokyo Disney (Disneyland).

• Check in to on-property Disney hotel (ideally Fantasy Springs Hotel, backup Tokyo Disneyland Hotel). Use your Vacation Package perks (park tickets included + attraction tickets).  

Day 4 – Tue 6/2 – Tokyo Disney (DisneySea + Fantasy Springs).

• Dive into Fantasy Springs (Frozen/Tangled/Peter Pan areas). Check the resort site for Happy Entry dates/availability near your stay.  

Day 5 – Wed 6/3 – Tokyo “green + style” day (easy pace).

• Meiji Jingu (shrine in a forest), Harajuku/Takeshita (teen fashion), Omotesando (design/streetwear), Shibuya (Scramble/center-gai). This is a good laundry/slow evening day.

Day 6 – Thu 6/4 – REST + ship luggage to Kyoto (important).

• Morning: sleep in. Ask your front desk to send your big suitcases to your Kyoto hotel (Takkyubin). Pack 24–36 hours of clothes/toiletries in your backpacks. Typical intercity delivery is next-day by evening; two days for longer distances. Afternoon: Ginza or Odaiba.  

Day 7 – Fri 6/5 – Tokyo → Kyoto (base 3 nights).

• Shinkansen (Nozomi) ~2h–2h15. Check into Kyoto hotel (your shipped bags should arrive today or by early evening). Sunset at Kiyomizu-dera, stroll Gion.  

Day 8 – Sat 6/6 – Kyoto West (Arashiyama).

• Early Arashiyama Bamboo Grove, Tenryu-ji, riverside walk; afternoon Kinkaku-ji (Golden Pavilion).

Day 9 – Sun 6/7 – Nara day-trip (optional, easy).

• Nara Park, Tōdai-ji Great Buddha, Kasuga Taisha. Buy official deer crackers (shika senbei) in-park and follow the safety etiquette. Return to Kyoto.  

Smart luggage move tonight (Sun):

• Ship your big suitcases from Kyoto straight to your final Tokyo hotel. Take only small backpacks to Osaka tomorrow for USJ. This “triangle shipping” skips hauling bags around Osaka and onto the Shinkansen later. (Next-day delivery typical.)  

Day 10 – Mon 6/8 – Universal Studios Japan (Osaka).

• Early JR trains Kyoto→Universal City (~1 hr). Express Pass with “Area Timed Entry” guarantees Super Nintendo World; otherwise use the official app for a free, limited Area Timed Entry slot after entering the park. Stay 1 night in Osaka (Namba or near Shin-Osaka).  

Day 11 – Tue 6/9 – Osaka → Tokyo (3 final nights).

• Brief Dotonbori photo-op, then Shinkansen back to Tokyo in the afternoon (~2h30 to Tokyo from Shin-Osaka). Check into your final Tokyo hotel—your shipped suitcases should already be waiting.  

Day 12 – Wed 6/10 – TeamLab + shopping.

• Pick one:
  • teamLab Borderless (Azabudai Hills, near Roppongi), or
  • teamLab Planets (Toyosu, extended through end-2027).Evening: Ginza or Nakano Broadway (otaku/vintage).  

Day 13 – Thu 6/11 – Tokyo free day + pack.

• Ideas: Shinjuku Gyoen garden, Tokyo Skytree views, Akasaka food finds.
• Send any bulky bags to the airport for pickup tomorrow (particularly helpful if you’re flying early/with connections). JAL ABC/Yamato offer airport delivery/pickup; follow their lead times/cutoffs.  

Day 14 – Fri 6/12 – Depart.

• Pick up airport-delivered luggage at the counter, breeze to security.  

There it is! Please let us know your thoughts. Thank you! 🙏