Arrive in Kyoto and meet your guide at your hotel. Please enjoy a welcome dinner at a local restaurant to get acquainted with the guide and learn more about the Nakasendo, regions we’ll be traveling through, and Japanese history and culture.

We will take a train from the hotel to Kibuneguchi Station and walk to Kifune Shrine, famous for its stunning stone steps lined with red lanterns, unique water fortune-telling (mizukuji). Afterwards, we will move to Ohara area, known as a peaceful escape with historic Buddhist temples and beautiful seasonal gardens.

•Walking Distance: 9-10km
•Elevation gain: 155m of ascent and 154m of descent (maximum)

Meet in the hotel lobby and take the train to Nara for hiking the Yamanobe no Michi, said to be Japan’s oldest road.

This ancient path is recorded as “Yamanobe no Michi” in the Kojiki and Nihon Shoki. Along the way, we’ll pass ancient shrines and temples like Ōmiwa Shrine and Chogakuji Temple, as well as ancient burial mounds associated with the early Yamato royal authority.

•Walking Distance: 13km
•Elevation gain: Elevation gain: 193 m of ascent and 166 m of descent (maximum)

In the morning we’ll take a private bus from Kyoto to Magome, where we’ll begin our walk to Tsumago.

Magome and Tsumago sit like facing bookends on the Kiso stretch of the old Nakasendō. Magome (the 43rd post town) climbs a cobbled slope and is known as the birthplace of novelist Shimazaki Tōson; much of its townscape was rebuilt after major fires in 1895 and 1915, then carefully restored to evoke the Edo-period feel.

Across the pass, Tsumago (the 42nd post town) became the pioneer of post-town preservation: residents launched a protection movement in 1968 and, in 1971, adopted a charter of “don’t sell, don’t rent, don’t demolish,” moving utilities out of sight and restricting traffic to keep the streetscape intact. In 1976 the town and surrounding landscape were designated an Important Preservation District—one of Japan’s earliest—and Tsumago is widely cited as the first town in Japan to commit to preserving its historic appearance.

•Walking Distance: 8.6 km
•Elevation gain: 330 m of ascent and 540 m of descent

We start high at Nenoue Pass and descend along the historic Yogawa-michi—a quiet ridge-and-hamlet route created as a detour when floods repeatedly damaged the main Nakasendō by the Kiso River. The pass marks the boundary between Yogawa and Nojiri. Expect cedar forest, mossy stone markers, small shrines, and farm hamlets – classic pastoral Japanese scenery and quiet walks on trails we’ll largely have all to ourselves.
Optionally, we could walk an extra hour all the way back to Tsumago.

At the end of the hike, the bus will take us back to Nagiso Onsen.

•Walking Distance: total 11.5 km
•Elevation gain: 330 m of ascent and 750 of descent

Climb from Yabuhara through a cedar forest and old stone paving to Torii Pass – a famed hard section of the Nakasendo. Along the way you’ll meet mossy stone Buddhas and haiku monuments (including those honoring the famous zen poet, Basho, reminders that this ridge was both a travel artery and a devotional path. The pass area is part of the Chūbu Nature Trail and included among assets of the Japan Heritage “Kiso Road,” with maintained footpaths that follow the historic line across the watershed before the gentle descent toward Narai.

Dropping into Narai-juku, the streets run nearly one kilometer in a continuous row of late-Edo machiya inns and merchant houses. The townscape escaped major fires in the modern era and was designated an Important Preservation District for Groups of Traditional Buildings in 1978, preserving one of the most evocative post-town scenes in Japan.

Craft is part of the story here: nearby Kiso-Hirasawa became a center of Kiso lacquerware, with wares historically sold through Narai’s post-town markets and carried along the Nakasendō toward Edo and Osaka – traditions you can still browse in shops and small museums today.

After the walk, our bus will take us to Matsumoto.

•Walking Distance: total 6 km
•Elevation gain: 300 m of ascent and 350 of descent

In the early morning, begin inside one of Japan’s few surviving original castles, Matsumoto Castle, a flatland fortress with a black-lacquered keep dating to the late 16th century and designated a National Treasure. Expect steep ladders, arrow-slits, and views to the Alps from the top floor.

Afterwards, free at your leisure until leaving for Tokyo. Wander a historic shopping district famous for its beautifully preserved Edo-period kura (traditional storehouses) with distinctive black-and-white patterned walls and enjoy great spots for snacks and antiques.

Take an express train to Shinjuku. After checking into the hotel, dinner will be a farewell party.

The tour ends after breakfast. Your guide will be available to offer suggestions and assistance with any further adventures you may wish to have while you are in Japan!