Itinerary
Travel back in time with the 11-day Walk the Nakasendo Trail, a self-guided trekking tour that traces the legendary route between Osaka and Tokyo. This journey takes experienced travelers through scenic mountain villages, lush valleys, and remnants of feudal Japan, with all accommodations, transport, and meals thoughtfully provided. Enjoy moderate hiking each day as you stroll historic post towns and forested paths that once linked Kyoto and Edo (modern Tokyo).
What sets this journey apart is the authentic immersion into Japan’s rural charms, where travelers can savor traditional hospitality and discover centuries-old architecture along the Nakasendo. For those who relish moderate-level hiking and cultural exploration, this trekking tour offers a window into the beauty and history of Japan’s heartland.
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).

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