Walk the Nakasendo Trail

Walking Japan's Nakasendo Trail

Walk the Nakasendo Trail

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Trip Fee

$ 5.300

Single Room Difference

$ 1.065

Date

01 - 11 November 2025

Trip Information

The Nakasendo Trail or 'Road through the Central Mountains' was part of Japan's network of highways. Travellers moving between Kyoto and Tokyo took several days to travel the Nakasendo, staying overnight in Juku post towns. In the seventeenth century, the Nakasendo was crowded with travellers, including feudal lords, samurai, itinerant merchants, and pilgrims. Now largely forgotten and quiet, the road provides a pleasant trail through scenic countryside and the history of Japan. Explore the fascinating city of Kyoto before starting the Nakasendo Trail, your trip ends in the sprawling city of Tokyo. Famous for its beautifully built Buddhist temples and traditional teahouses, Kyoto is a great introduction to your Japanese adventure. From here, you can visit the historical city of Nara, full of cultural treasures and tranquil gardens. In Tokyo you can experience the whole breadth of Japanese arts and culture, not to mention the abundance of culinary treasures. An ever-evolving city, Tokyo is an explosion for the senses with a discovery around every corner.

Activity Areas

Self-Guided Walking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking
Walking & Trekking

Region & Country & City

Japan

Included in the Price


- 10 nights’ accommodation in hotels and Japanese-style inns (ryokan/minshuku)
- All breakfasts & 5 dinners
- Management by your local Headwater appointed agent
- Route directions and maps
- Luggage transfers between accommodation from Magome to Matsumoto
- Train from Kyoto to trail starting point and from trail end point to Tokyo

Not Included In The Price


- Lunches
- Travel insurance
- Single supplements
- Solo traveller supplement (where only one person is travelling on a departure date)
- Visas and vaccinations

Itinerary

Day 1 Arrive in Kyoto

Take the express train from Osaka Kansai Int. Airport to Kyoto City (approx. 70mins), then a local taxi to your first hotel. (approx. 10mins). Overnight Kyoto.

Day 2 Explore Kyoto

Enjoy a rest day in the incredible city of Kyoto, famous for its Buddhist temples, tranquil gardens, and traditional teahouses. We recommend visiting the historical city of Nara, full of cultural treasures and expansive parks, located approx. 1hr from Kyoto city on the train. Overnight Kyoto.

Day 3 Kuramaa to Kibune

Take the train to the hills of northern Kyoto (included), on sacred Mount Kurama. Here, Samurai trained with mountain Buddhist practitioners in the 12th century. From Kurama Temple, walk to the Kifune Shrine, which is known for bringing good fortune to those seeking luck in love. The walk begins with a steep and long ascent up stone steps to the Kurama Temple. Stop to take in the beautiful scenery and spend some time at the shrines and smaller temples along the way. Return by local train to Kyoto (included). The remainder of your day is free for you to explore Kyoto. Overnight Kyoto.

Day 4 Magome to Tsumago

Begin with a train journey from Kyoto to Nakatsugawa, including a ride on the world-famous Shinkansen (Bullet Train) to Nagoya (included). At Nakatsugawa, you board a local bus for the short journey to Magome. Walk over Magome Pass to Tsumago, one of the best preserved and most evocative of the Nakasendo post towns. Spend the night at a family-run Minshuku in Tsumago or the nearby hamlet of O-Tsumago, with a delicious home-cooked Japanese dinner and breakfast included. Overnight Minshuku Guesthouse, Tsumago.

Day 5 Tsumago/Nagiso to Nojiri

Today is your longest day on the trail and is a beautiful and varied hike from Tsumago or Nagiso to Nojiri. The trail travels through small valleys and past forests of bamboo and Japanese cedar, through some of the least-developed scenery on the tour. Continue by train to Kiso-Fukushima (included). Stay at a lovely hot-spring Ryokan set in a peaceful valley above the town. Complimentary transfer from the station is provided by the Ryokan.   Overnight Ryokan (traditional Japanese inn), Kiso-Fukushima.

Day 6 Gongentaki Waterfall

If you have free time in Kiso Fukushima, you can take this optional walk from Kiso Fukushima Station to Gongentaki Waterfall. The trail combines a riverside path, a dirt trail leading up to the waterfall, and gentle descent back down through a quiet neighbourhood with good views over the town and the traditional buildings near the Nakasendo Trail. Overnight Ryokan (traditional Japanese inn), Kiso-Fukushima.

Day 7 Yabuhara to Matsumoto

The Ryokan will drive you back to Kiso-Fukushima after breakfast if you're staying outside the village. From here, you take the train to Yabuhara (included) which is the starting point for your walk over the Torii pass to Narai. Explore this atmospheric village before you continue on today's journey to the small town of Kiso-Hirasawa, famous for its lacquerware. There are many small shops selling beautifully crafted tableware and furniture. From Kiso-Hirasawa, take the train to the castle town of Matsumoto for your overnight stay. Your hosts will serve a home-cooked Japanese dinner and breakfast. Overnight Minshuku Guesthouse, Matsumoto .

Day 8 Free Day in Matsumoto

After breakfast, you will have free time to explore the castle town of Matsumoto. This historic town is home to the iconic artist Yayoi Kusama and the largest collection of Ukiyo-e wood blocks. With many things to see and do Matsumoto is a destination in and of itself. Be sure to visit the well-preserved Matsumoto Castle also known as the 'Black Crow Castle'. You can enter the castle and enjoy the unique architecture, hidden nooks, and panoramic views of the castle town. This afternoon head onward to Karuizawa where you will stay this evening and enjoy a natural hot spring baths before your final walk to Yokokawa. Your included luggage transfer ends here. To continue the service from Matsumoto to Tokyo, you can arrange this locally with your inn in the morning who will liaise with the long distance courier Takkyubin; this is paid for locally (approx. £16 per bag/20kg). Using this service, you will be without your luggage from the morning of day 8, until the evening of day 9. Overnight Ryokan (traditional Japanese inn), Karuizawa/Komoro.

Day 9 Karuizawa to Yokokawa

After breakfast, your final walk on the Nakasendo Trail is from Karuizawa to Yokokawa. Leaving Karuizawa, the trail takes you over the Usui-toge Pass and down a gentle descent along one of the most beautiful sections of the Nakasendo, and certainly the least-developed. From Yokokawa, take the local train to Takasaki and change there for your ride on the Shinkansen bullet train to Tokyo (approx. 3 hours - included). Overnight Tokyo.

Day 10 Rest Day in Tokyo

You have a full day in Tokyo to explore this vibrant city. Visit the glittering Ginza area with elegant department stores and food halls crammed with all kinds of unfamiliar delicacies. Or spend time among the skyscrapers of Shinjuku and pass-through Shinjuku station, the busiest transport hub in the world. Eat and drink in one of the myriad small bars and restaurants which cluster around most railway stations or splash out on an elegant meal in an upscale restaurant. Overnight Tokyo.

Day 11 Depart Tokyo

Enjoy breakfast at your hotel before walking to Hamamatsucho station (approx. 10mins) to take the monorail directly to Tokyo Haneda Airport (approx. 15mins - paid locally).

Travel Dates

01 - 11 November 2025 $ 5.300

02 - 12 November 2025 $ 5.300

03 - 13 November 2025 $ 5.300

04 - 14 November 2025 $ 5.300

05 - 15 November 2025 $ 5.300

06 - 16 November 2025 $ 5.300

07 - 17 November 2025 $ 5.300

08 - 18 November 2025 $ 5.300

09 - 19 November 2025 $ 5.300

10 - 20 November 2025 $ 5.300

11 - 21 November 2025 $ 5.300

12 - 22 November 2025 $ 5.300

13 - 23 November 2025 $ 5.300

14 - 24 November 2025 $ 5.300

15 - 25 November 2025 $ 5.300

16 - 26 November 2025 $ 5.300

17 - 27 November 2025 $ 5.300

18 - 28 November 2025 $ 5.300

19 - 29 November 2025 $ 5.300

23 November - 03 December 2025 $ 5.970

24 March - 03 April 2026 $ 5.930

25 March - 04 April 2026 $ 5.930

26 March - 05 April 2026 $ 5.930

27 March - 06 April 2026 $ 5.930

28 March - 07 April 2026 $ 5.930

29 March - 08 April 2026 $ 5.930

30 March - 09 April 2026 $ 5.930

31 March - 10 April 2026 $ 5.930

01 - 11 April 2026 $ 6.260

02 - 12 April 2026 $ 6.260

03 - 13 April 2026 $ 6.260

04 - 14 April 2026 $ 6.260

05 - 15 April 2026 $ 6.260

06 - 16 April 2026 $ 6.260

07 - 17 April 2026 $ 6.260

08 - 18 April 2026 $ 6.260

09 - 19 April 2026 $ 6.260

10 - 20 April 2026 $ 6.260

11 - 21 April 2026 $ 6.260

12 - 22 April 2026 $ 6.260

13 - 23 April 2026 $ 6.260

14 - 24 April 2026 $ 6.260

15 - 25 April 2026 $ 6.260

16 - 26 April 2026 $ 6.260

17 - 27 April 2026 $ 6.260

18 - 28 April 2026 $ 6.260

19 - 29 April 2026 $ 6.260

20 - 30 April 2026 $ 6.260

21 April - 01 May 2026 $ 6.260

22 April - 02 May 2026 $ 6.260

23 April - 03 May 2026 $ 6.260

24 April - 04 May 2026 $ 6.260

25 April - 05 May 2026 $ 6.260

26 April - 06 May 2026 $ 6.260

27 April - 07 May 2026 $ 6.260

28 April - 08 May 2026 $ 6.260

29 April - 09 May 2026 $ 6.260

30 April - 10 May 2026 $ 6.260

01 - 11 May 2026 $ 5.930

02 - 12 May 2026 $ 5.930

03 - 13 May 2026 $ 5.930

04 - 14 May 2026 $ 5.930

05 - 15 May 2026 $ 5.930

06 - 16 May 2026 $ 5.930

07 - 17 May 2026 $ 5.930

08 - 18 May 2026 $ 5.930

09 - 19 May 2026 $ 5.930

10 - 20 May 2026 $ 5.930

11 - 21 May 2026 $ 5.930

12 - 22 May 2026 $ 5.930

13 - 23 May 2026 $ 5.930

14 - 24 May 2026 $ 5.930

15 - 25 May 2026 $ 5.930

16 - 26 May 2026 $ 5.930

17 - 27 May 2026 $ 5.930

18 - 28 May 2026 $ 5.930

19 - 29 May 2026 $ 5.930

20 - 30 May 2026 $ 5.930

21 - 31 May 2026 $ 5.930

22 May - 01 June 2026 $ 5.930

23 May - 02 June 2026 $ 5.930

24 May - 03 June 2026 $ 5.930

25 May - 04 June 2026 $ 5.930

26 May - 05 June 2026 $ 5.930

27 May - 06 June 2026 $ 5.930

28 May - 07 June 2026 $ 5.930

29 May - 08 June 2026 $ 5.930

30 May - 09 June 2026 $ 5.930

31 May - 10 June 2026 $ 5.930

01 - 11 June 2026 $ 5.930

02 - 12 June 2026 $ 5.930

03 - 13 June 2026 $ 5.930

04 - 14 June 2026 $ 5.930

05 - 15 June 2026 $ 5.930

06 - 16 June 2026 $ 5.930

07 - 17 June 2026 $ 5.930

08 - 18 June 2026 $ 5.930

09 - 19 June 2026 $ 5.930

10 - 20 June 2026 $ 5.930

11 - 21 June 2026 $ 5.930

12 - 22 June 2026 $ 5.930

13 - 23 June 2026 $ 5.930

14 - 24 June 2026 $ 5.930

15 - 25 June 2026 $ 5.930

16 - 26 June 2026 $ 5.930

17 - 27 June 2026 $ 5.930

18 - 28 June 2026 $ 5.930

19 - 29 June 2026 $ 5.930

20 - 30 June 2026 $ 5.930

21 June - 01 July 2026 $ 5.930

22 June - 02 July 2026 $ 5.930

23 June - 03 July 2026 $ 5.930

24 June - 04 July 2026 $ 5.930

25 June - 05 July 2026 $ 5.930

26 June - 06 July 2026 $ 5.930

27 June - 07 July 2026 $ 5.930

28 June - 08 July 2026 $ 5.930

29 June - 09 July 2026 $ 5.930

30 June - 10 July 2026 $ 5.930

01 - 11 July 2026 $ 6.260

02 - 12 July 2026 $ 6.260

03 - 13 July 2026 $ 6.260

04 - 14 July 2026 $ 6.260

05 - 15 July 2026 $ 6.260

06 - 16 July 2026 $ 6.260

07 - 17 July 2026 $ 6.260

08 - 18 July 2026 $ 6.260

09 - 19 July 2026 $ 6.260

10 - 20 July 2026 $ 6.260

11 - 21 July 2026 $ 6.260

12 - 22 July 2026 $ 6.260

13 - 23 July 2026 $ 6.260

14 - 24 July 2026 $ 6.260

15 - 25 July 2026 $ 6.260

16 - 26 July 2026 $ 6.260

17 - 27 July 2026 $ 6.260

18 - 28 July 2026 $ 6.260

19 - 29 July 2026 $ 6.260

20 - 30 July 2026 $ 6.260

21 - 31 July 2026 $ 6.260

22 July - 01 August 2026 $ 6.260

23 July - 02 August 2026 $ 6.260

24 July - 03 August 2026 $ 6.260

25 July - 04 August 2026 $ 6.260

26 July - 05 August 2026 $ 6.260

27 July - 06 August 2026 $ 6.260

28 July - 07 August 2026 $ 6.260

29 July - 08 August 2026 $ 6.260

30 July - 09 August 2026 $ 6.260

31 July - 10 August 2026 $ 6.260

01 - 11 August 2026 $ 6.260

02 - 12 August 2026 $ 6.260

03 - 13 August 2026 $ 6.260

04 - 14 August 2026 $ 6.260

05 - 15 August 2026 $ 6.260

06 - 16 August 2026 $ 6.260

07 - 17 August 2026 $ 6.260

08 - 18 August 2026 $ 6.260

09 - 19 August 2026 $ 6.260

10 - 20 August 2026 $ 6.260

11 - 21 August 2026 $ 6.260

12 - 22 August 2026 $ 6.260

13 - 23 August 2026 $ 6.260

14 - 24 August 2026 $ 6.260

15 - 25 August 2026 $ 6.260

16 - 26 August 2026 $ 6.260

17 - 27 August 2026 $ 6.260

18 - 28 August 2026 $ 6.260

19 - 29 August 2026 $ 6.260

20 - 30 August 2026 $ 6.260

21 - 31 August 2026 $ 6.260

22 August - 01 September 2026 $ 6.260

23 August - 02 September 2026 $ 6.260

24 August - 03 September 2026 $ 6.260

25 August - 04 September 2026 $ 6.260

26 August - 05 September 2026 $ 6.260

27 August - 06 September 2026 $ 6.260

28 August - 07 September 2026 $ 6.260

29 August - 08 September 2026 $ 6.260

30 August - 09 September 2026 $ 6.260

31 August - 10 September 2026 $ 6.260

01 - 11 September 2026 $ 6.260

02 - 12 September 2026 $ 6.260

03 - 13 September 2026 $ 6.260

04 - 14 September 2026 $ 6.260

05 - 15 September 2026 $ 6.260

06 - 16 September 2026 $ 6.260

07 - 17 September 2026 $ 6.260

08 - 18 September 2026 $ 6.260

09 - 19 September 2026 $ 6.260

10 - 20 September 2026 $ 6.260

11 - 21 September 2026 $ 6.260

12 - 22 September 2026 $ 6.260

13 - 23 September 2026 $ 6.260

14 - 24 September 2026 $ 6.260

15 - 25 September 2026 $ 6.260

16 - 26 September 2026 $ 6.260

17 - 27 September 2026 $ 6.260

18 - 28 September 2026 $ 6.260

19 - 29 September 2026 $ 6.260

20 - 30 September 2026 $ 6.260

21 September - 01 October 2026 $ 6.260

22 September - 02 October 2026 $ 6.260

23 September - 03 October 2026 $ 6.260

24 September - 04 October 2026 $ 6.260

25 September - 05 October 2026 $ 6.260

26 September - 06 October 2026 $ 6.260

27 September - 07 October 2026 $ 6.260

28 September - 08 October 2026 $ 6.260

29 September - 09 October 2026 $ 6.260

30 September - 10 October 2026 $ 6.260

01 - 11 October 2026 $ 6.260

02 - 12 October 2026 $ 6.260

03 - 13 October 2026 $ 6.260

04 - 14 October 2026 $ 6.260

05 - 15 October 2026 $ 6.260

06 - 16 October 2026 $ 6.260

07 - 17 October 2026 $ 6.260

08 - 18 October 2026 $ 6.260

09 - 19 October 2026 $ 6.260

10 - 20 October 2026 $ 6.260

11 - 21 October 2026 $ 6.260

12 - 22 October 2026 $ 6.260

13 - 23 October 2026 $ 6.260

14 - 24 October 2026 $ 6.260

15 - 25 October 2026 $ 6.260

16 - 26 October 2026 $ 6.260

17 - 27 October 2026 $ 6.260

18 - 28 October 2026 $ 6.260

19 - 29 October 2026 $ 6.260

20 - 30 October 2026 $ 6.260

21 - 31 October 2026 $ 6.260

22 October - 01 November 2026 $ 6.260

23 October - 02 November 2026 $ 6.260

24 October - 03 November 2026 $ 6.260

25 October - 04 November 2026 $ 6.260

26 October - 05 November 2026 $ 6.260

27 October - 06 November 2026 $ 6.260

28 October - 07 November 2026 $ 6.260

29 October - 08 November 2026 $ 6.260

30 October - 09 November 2026 $ 6.260

31 October - 10 November 2026 $ 6.260

01 - 11 November 2026 $ 5.630

02 - 12 November 2026 $ 5.630

03 - 13 November 2026 $ 5.630

04 - 14 November 2026 $ 5.630

05 - 15 November 2026 $ 5.630

06 - 16 November 2026 $ 5.630

07 - 17 November 2026 $ 5.630

08 - 18 November 2026 $ 5.630

09 - 19 November 2026 $ 5.630

10 - 20 November 2026 $ 5.630

11 - 21 November 2026 $ 5.630

12 - 22 November 2026 $ 5.630

13 - 23 November 2026 $ 5.630

14 - 24 November 2026 $ 5.630

15 - 25 November 2026 $ 5.630

16 - 26 November 2026 $ 5.630

17 - 27 November 2026 $ 5.630

18 - 28 November 2026 $ 5.630

19 - 29 November 2026 $ 5.630

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