4 days of Japan: Tokyo → Kyoto → Osaka

4 days · 20 stops · kept in September 2026

Outdoors & foodFood Outdoors

Tokyo → Kyoto → Osaka

All 4 days at once. Each day is its own line — nothing is drawn across a night.

On footBy train or taxi

2 playbooks shared · added to 0 trips

All 4 days, as they ran them

Day 12:30 pm – 10:30 pm · 4 stops
2:30 pm 1
Land at HanedaTokyo
15 min by train or taxi · 15 km
5 pm 2
Check in at Trunk HotelTokyo
Bags to the room, then straight out — nobody sleeps yet.
8 min by train or taxi · 2.2 km
7 pm 3
Dinner at GonpachiTokyo
19 min walk · 1.4 km
9 pm 4
Nightcap at Bar TrenchTokyo
(Sam K + Jonah M)
Day 26:30 am – 9:30 pm · 6 stops
6:30 am 5
Fushimi Inari at dawnKyoto
Go before 7 am or the gates are shoulder to shoulder.
8 min by train or taxi · 3.7 km
9 am 6
Breakfast at % ArabicaKyoto
9 min walk · 700 m
10:30 am 7
Kiyomizu-dera and SannenzakaKyoto
11 min walk · 800 m
12 pm 8
Lunch at Omen KodaijiKyoto
20 min walk · 1.5 km
4 pm 9
Nishiki MarketKyoto
(Jonah M + Mei T)
5 min walk · 400 m
7:30 pm 10
Dinner at Giro Giro HitoshinaKyoto
Day 310 am – 9:30 pm · 5 stops
10 am 11
Train Kyoto → OsakaKyoto
40 min by train or taxi · 40 km
11:30 am 12
Check in at Zentis OsakaOsaka
19 min walk · 1.4 km
12:30 pm 13
Lunch at Harukoma SushiOsaka
8 min by train or taxi · 2.6 km
3 pm 14
Osaka Castle ParkOsaka
8 min by train or taxi · 3.1 km
7 pm 15
Dōtonbori food crawlOsaka
Five stops, one bite each. Jonah is picking.
Day 48 am – 9 pm · 5 stops
8 am 16
Breakfast at the hotelOsaka
8 min by train or taxi · 4.1 km
9:30 am 17
Shinkansen to TokyoOsaka
3h by train or taxi · 396 km
12:30 pm 18
Last lunch at MaisenTokyo
14 min by train or taxi · 14 km
4:30 pm 19
Transfer to HanedaTokyo
3 min walk · 0 m
8:10 pm 20
Flight homeTokyo
Check-in opens 5:10 pm.