Tour overview

This 11-day self-guided holiday walks the Nakasendo, the old samurai highway between Kyoto and Tokyo, through the Kiso Valley. There is no group or guide; you walk at your own pace with detailed notes and local support. You stay ten nights in hotels, ryokan and minshuku inns, with breakfast daily and five dinners.

After a rest day in Kyoto you walk over the sacred mountain of Kurama to Kibune. A train takes you to Nakatsugawa to walk the classic section from Magome to Tsumago, two beautifully preserved post towns.

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Your longest day follows the river to Nojiri, with an optional walk to the Gongentaki waterfall, then on via Yabuhara to Matsumoto and its black castle. A final walk over the Usui Pass from Karuizawa leads to Tokyo for a rest day.

The physical rating is moderate to challenging. This holiday suits independent walkers who want to step back into old Japan.

Trip highlights

  • A day in Kyoto (Day 2)
  • Kurama to Kibune (Day 3)
  • Magome to Tsumago (Day 4)
  • The Kiso Valley (Days 5–7)
  • Matsumoto Castle (Day 8)
  • The Usui Pass (Day 9)

Your route

12 stops from Kyoto to Tokyo

11-day route: Kyoto – Kurama – Magome – Tsumago – Nojiri – Yabuhara – Matsumoto – Karuizawa – Tokyo
  1. Kyoto Days 1–3
  2. Nara Day 2
  3. Kurama Day 3
  4. Magome Day 4
  5. Tsumago Day 4
  6. Nojiri Day 5
  7. Kiso-Fukushima Day 6
  8. Narai Day 7
  9. Matsumoto Day 7
  10. Karuizawa Day 8
  11. Yokokawa Day 9
  12. Tokyo Days 9–11

Why choose this tour

Preserved post towns on a historic highway. Nights in traditional inns with dinners.

Best suited to

  • Independent walkers
  • History lovers
  • Couples and friends
  • Active travellers
A woman with a red umbrella in a Kiso Valley post town

Day-by-day itinerary

11 days from Osaka, Japan to Tokyo, Japan

  1. Day 1 · Osaka, Kyoto Kyoto

    Arrive in Japan.

    Hotel
    Hotel
  2. Day 2 · Kyoto Kyoto

    A rest day.

    Hotel
    Hotel
    Meals
    Breakfast
  3. Day 3 · Kurama, Kibune Kurama to Kibune

    A sacred mountain.

    Hotel
    Hotel
    Meals
    Breakfast
  4. Day 4 · Magome, Tsumago Magome to Tsumago

    Two post towns.

    Hotel
    Minshuku guesthouse
    Meals
    Breakfast, Dinner
  5. Day 5 · Nagiso, Nojiri Tsumago to Nojiri

    The longest day.

    Hotel
    Ryokan
    Meals
    Breakfast, Dinner
  6. Day 6 · Gongentaki Waterfall Gongentaki

    An optional walk.

    Hotel
    Ryokan
    Meals
    Breakfast, Dinner
  7. Day 7 · Yabuhara Yabuhara

    Through the valley.

    Hotel
    Minshuku guesthouse
    Meals
    Breakfast, Dinner
  8. Day 8 · Matsumoto Castle Matsumoto

    A castle town.

    Hotel
    Ryokan
    Meals
    Breakfast, Dinner
  9. Day 9 · Karuizawa, Yokokawa, Tokyo Usui Pass

    The final walk.

    Hotel
    Hotel
    Meals
    Breakfast
  10. Day 10 · Tokyo Tokyo

    A rest day.

    Hotel
    Hotel
    Meals
    Breakfast
  11. Day 11 · Tokyo Tokyo

    The holiday ends.

    Meals
    Breakfast
The historic street of Narai-juku

Where you stay

  • Kyoto (3 nights) Hotel
  • Tsumago (1 night) Minshuku guesthouse
  • Nojiri (2 nights) Ryokan
  • Yabuhara (1 night) Minshuku guesthouse
  • Matsumoto (1 night) Ryokan
  • Tokyo (2 nights) Hotel

Hotel names are indicative and may be replaced with a property of similar standard and location.

What's included

Included

  • Accommodation 10 nights in hotels and traditional inns
  • Meals 10 breakfasts and 5 dinners
  • Rail travel between trail sections
  • Luggage transfers on the trail
  • Detailed route notes and maps
  • Local emergency support

Not included

  • Flights
  • Meals not included 9 lunches and 5 dinners
  • Local transport
  • Travel insurance and personal spending
Matsumoto Castle

This trip might not be for you if…

Honest disclaimer — please read

  • You want a guide or group
  • You dislike long walking days
  • You want luxury hotels throughout
  • You want flights included — they are not

Good to know

Meals by day Breakfast: Days 2–11 · Lunch: none included · Dinner: Days 4–8
FCDO advice UK FCDO travel advice for Japan
A street lined with wooden buildings in the Kiso Valley

In pictures

Departures & prices

From £3,789 per person, twin share, tour only. 289 upcoming departures.

Frequently asked questions

How do I book this tour?

Tap any "Enquire" button on the page and one of our travel specialists will be in touch within 24 hours (often same day). We'll confirm availability on your preferred date, run through anything you need to know, and only ask for the deposit once you've decided.

What financial protection do I get?

Every Travelisto booking is 100% financially protected. Your money is held in a ring-fenced Trust account until you return from your trip, and we are members of the Protected Trust Services scheme (PTS 6035). Most tours also include ATOL protection where flights are part of the package.

Is there a guide?

No, this is a self-guided holiday with route notes and local support.

Do I need a visa for Japan?

No, UK citizens can visit Japan visa-free for up to 90 days.

How hard is the walking?

Moderate to challenging, with some long days and climbs.

Is my luggage moved for me?

Yes, on most trail days.

What are ryokan and minshuku like?

Traditional Japanese inns with futon bedding on tatami floors, often with shared or communal hot-spring baths.

When can I start?

On almost any day through the walking season.

Can you tailor the trip?

Yes — every escorted tour can be modified into a private tailor-made version with your own dates, adjusted pace, upgraded hotels and add-on extensions. Tell us what you'd like changed when you enquire and we'll quote it both ways so you can compare.

What if my flight is delayed or cancelled?

If your international flight is part of your booking through us, we re-book at no cost. If you've booked flights separately, the tour's local team holds your transfer slot until you arrive. We strongly recommend a comprehensive travel insurance policy that includes delay and cancellation cover.

ATOL protected 100% financially protected in a Trust bank account PTS 6035 4.7 on Trustpilot
Tailor-made option

Not quite the right fit? Make it tailor-made.

If this group tour doesn't match your ideal trip, our specialists will turn it into a private tailor-made journey — your own dates, your own pace, upgraded hotels where you want them, and the parts you don't love swapped out. Same destinations, just rebuilt around you.

Contact us for a tailor-made version of this itinerary

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