10 March – 30 March 2027 · 20 nights · 5 friends

Tokyo to Osaka
by way of the Nakasendo.

A week in Tokyo, four nights of castles, post towns and onsen in the Japanese Alps, five nights in Kyoto as the first cherries open, and four nights eating our way through Osaka. Culture, hiking, museums, food. Nightlife optional.

Tokyo · 7 nightsMatsumoto & Kiso · 4 nightsKyoto · 5 nightsOsaka · 4 nights
Itinerary

21 days planned, each with a rain alternative.
Where to stay

24 districts shortlisted for a whole place for five.
Things to do

Temples, hikes, gardens and museums, filterable on a map.
Eat

Shortlists per city with reservation notes for a table of five.
Logistics

Rail pass math, IC cards, eSIM, luggage forwarding, budget, booking dates.

The shape of the trip

  1. Tokyo · 10 March → 17 March

    First-timer core done early in the morning, museums in the afternoons, one mountain day when the museums close on Monday.

  2. Matsumoto & Kiso · 17 March → 21 March

    Castle and two onsen nights at Asama, then down the Kiso Valley to sleep in Tsumago and walk the Nakasendo from Magome. Exit south via Nakatsugawa, not back through Matsumoto.

  3. Kyoto · 21 March → 26 March

    A machiya for five. Dawn at Fushimi Inari, the quiet sub-temples for the returners, Uji tea, and the early-blooming sakura spots from the 25th.

  4. Osaka · 26 March → 30 March

    An apartment in Minami. Nara day, Himeji or Kobe day, and a lot of eating. Shinkansen back to Shinagawa for the flight home.

Decisions already made

  • No JR Pass. Point-to-point for this route is about ¥57,000 per person. A 21-day pass would cost roughly €300 more each.
  • Leave the Kiso Valley southwards. Nagiso → Nakatsugawa → Nagoya → Kyoto saves ~€20 pp and half a day versus backtracking to Matsumoto.
  • Asama over Shirahone. Shirahone's riverside bath is closed until late April and the bus takes two hours. Asama has private baths and is 20 minutes from the castle.
  • Bags travel with us. One suitcase each, carried on every train. On the Tokaido Shinkansen anything over 160 cm combined needs the free reserved oversized-baggage seat; under that, the overhead rack is enough.
  • Sakura is a bonus, not a plan. Tokyo's main bloom starts after we leave. Shinjuku Gyoen's early varieties, then Kyoto and Osaka from the 25th.
  • Budget ≈ €3,000 per person excluding flights, if Kyoto and Osaka are booked by October 2026.

Dates that cannot be fixed later

Now → Oct 2026
Kyoto machiya and Osaka apartment for five. Sakura season, thin market.
Oct–Dec 2026
Asama ryokan (2 nights, half-board) and Tsumago minshuku (2 nights). Tsumago has almost no beds.
1 Jan 2027, 10:00 JST
Yayoi Kusama Museum tickets for March (Thu–Sun only).
10 Feb 2027, 10:00 JST
Ghibli Museum, all March dates, via Lawson international.
17 Feb 2027, 10:00 JST
Azusa Shinjuku → Matsumoto seats on eki-net.
28 Feb 2027, 10:00 JST
Nozomi Shin-Osaka → Shinagawa on SmartEX, five seats plus the oversized-baggage row.

241 researched places on the map. Prices researched September 2026 at 1 EUR ≈ ¥180. Verify before booking.