Itinary Check – Travel with Teenagers

We are practically giddy waiting for our trip to Japan in a few weeks. I (45m) have been dreaming of a trip to Japan since I was in grade 6 when my best friend moved to Japan in the 90s. I am so excited that my wife (45f) and two boys (14m) and (12m) are just as excited to explore Japan as well – we have been planning this trip for years!

Because of the boys school schedule, we can save them from missing too much school by going over their spring break, but it also means we are going at the height of cherry blossom season – I’m a bit nervous about it, but I’ve made my peace that we’ll just have to try and schedule off-peak activities to avoid really large crowds.

It’s a 14 day trip (not including travel) – but I have tried to keep things pretty open. Some days we just have areas/regions to explore but no rigid plans. The only thing we have really booked ahead of time is TeamLabs Borderless, a Yamouri Giants Baseball Game, and the Samurai/Ninja museum.

However, I would like some thoughts on our itinerary, and maybe some comment on anyone’s experiences/activities for the boys that maybe we have missed. Also, we are totally interested in exploring around Tokyo in the night and don’t mind our boys learning a bit of the nightlife experience, but I am not sure about Kabukicho on a Thursday night… We aren’t drinkers so there won’t be any bar visits, just general night time exploring with all the lights, sights, and sounds…

Itinerary:

03/29/2026 – Sunday

Day 1: Travel (Canada to Tokyo-Narita Airport)

TOKYO

03/30/2026 – Monday

Day2: Travel (Canada to Tokyo) LOST DAY TO TRAVEL

– Travel from Narita Airport to Shinagawa (Narita Express)

– Hotel Checkin

– First meal in Japan

03/31/2026 – Tuesday

Day 3: Day of rest

– Jet lag recovery

– Shinagawa- Exploring around hotel

– TeamLab Borderless (Booked)

– Tokyo Tower

04/01/2026 – Wednesday

Day 4: Tokyo 1 – Shibuya (LATER AFTERNOON/NIGHT)

– Shibuya Scramble Crossing

– Diakanyama

– Dogenzaka

O4/02/2026 – Thursday

Day 5: Tokyo 2 – Shinjuku (LATER AFTERNOON/NIGHT)

– Shinjuku Gyoen National Garden (Earlier in the afternoon, before sunset)

– Kabukicho (At night!) (Karaoke, maybe)

– Omoide Yokocho

O4/03/2026 – Friday

Day 6: Tokyo 3 – Akihabara (LATER AFTERNOON/NIGHT)

– Arcade Games

– Anime/Menga/Comic Books/Models

– Capsule Store

04/04/2026 – Saturday

Day 7: Tokyo 4 – Tokyo Yomuiri Giants vs. The Yokohama Baystars at the Tokyo Dome (Booked)

KYOTO

04/05/2026 – Sunday

Day 8: Travel to Kyoto (Shinkansen)

– Hotel Checkin

– Explore around Kyoto Hotel

– More this day, maybe?

– Fushimi Inari Taisha (Orange Gates Walking Tour)?

04/06/2026 – Monday

Day 9: Kyoto 1 – Gion District

– Yasaka Shrine

– Maruyama Park

– Nishiki Market

– Shinkyogoku Market

OSAKA

04/07/2026 – Tuesday

Day 10: Travel to Osaka (Day Trip)

– Dotonbori

– DenDen Town

– Shinsekai Market

KYOTO

04/08/2026 – Wednesday

Day 11: Kyoto 2 – Arishiyama

– Bamboo Grove

– Tenryu-ji Shrine

– Arishiyama Monkey Park Iwatayama

NARA

04/09/2026 – Thursday

Day 12: Travel to Nara (Day Trip)

– Todai-ji Buddhist Temple

– Nara Deer Park

TOKYO

04/10/2026 – Friday

Day 13: Travel (Kyoto to Tokyo) (Shinkansen)

– Hotel Checkin (Asakusa)

– Explore around Asakusa

– Senso-ji Shrine (Oldest Shrine in Tokyo)

– Samurai/Ninja Museum (Booked)

04/11/2026 – Saturday

Day 14: Tokyo 5 – Totally open! (Revisit areas, shopping, etc)

04/12/2026 – Sunday

Day 15: Tokyo 6 – Totally open ! (Revisit areas, shopping, etc)

04/13/2026 – Monday

Day 16: Travel (Tokyo-Narita Airport to Canada)

– Travel from Asakusa to Narita Airport

Thoughts? Ideas? Comments? All welcome…

by 88_aa