In the morning, meet your guides in the foyer of the Royal Park Sanjo Hotel Kyoto at 9 a.m. The first top of the adventure is one of the city’s most iconic sites: the Fushimi Inari Shrine. Walking through its thousands of vivid orange torii gates is a mesmerizing experience, as the tunnel-like path winds through the forest and up the hillside. The walk is both visually stunning and deeply spiritual, culminating in sweeping views of Kyoto from the summit. Afterward, we enjoy lunch at a local restaurant featuring traditional Japanese cuisine. Returning to The Royal Park Hotel Kyoto Sanjo, there’s time to relax before our special afternoon experience—a Japanese tea ceremony. Dressed in exquisite kimonos (with hair styling for women), we learn the graceful art of tea preparation, a practice that fosters mindfulness and simplicity. This cultural highlight concludes with a group dinner at a local restaurant, accompanied by wine.

Meals: Lunch, dinner
Hiking: 6 km (3.7 mi), 3 hours
Terrain: Stone paths, forest trails, hillside stairways
Accommodation: The Royal Park Hotel Kyoto Sanjo

After breakfast at the hotel, we transfer by private vehicle from Kyoto to Hosokute-juku, a tranquil and lesser-visited post town along the Nakasendō Trail. Today’s walk takes us from Hosokute-juku to Okute-juku, one of the most beautifully preserved and scenic stretches of the route. The trail winds through quiet forest, historic stone-paved paths, and gently rolling countryside, offering an authentic experience of rural Japan. Along the way, we pass moss-covered waymarkers, serene shrines, and traditional thatched-roof farmhouses that reflect centuries of travel along this ancient road. As we near Okute-juku, the landscape opens to views of surrounding hills and farmland, showcasing the natural beauty of the Gifu region. At the end of the walk, we meet our private vehicle and continue to Ena for a hands-on Hiroshige ukiyo-e woodblock printmaking workshop. Later, we check into Enakyo Onsen Hotel Yurisha and enjoy dinner with wine.

Meals: Breakfast, lunch, dinner
Hiking: 11 km (6.8 mi), 4 hours
Elevation: +450 m (1,476 ft), -480 m (1,575 ft)
Terrain: Forest trails, stone paths, undulating hills
Accommodation: Enakyo Onsen Hotel Yurisha

After an enjoyable breakfast, we begin today’s journey with a scenic walk to the beautifully preserved post town of Magome. We stroll through its cobblestone streets, passing wooden watermills and traditional houses that embody Edo-era Japan. From Magome, the trail ascends gradually toward the serene Magome Pass. As we climb, the scenery shifts from open countryside to the tranquil forests of the Kiso Valley. Midway, we pause at a traditional Japanese home, where hosts in period attire serve warm tea beside an irori hearth—a charming glimpse into local culture. Reenergized, we continue through lush woodland, passing a pair of picturesque waterfalls before reaching the timeless village of Tsumago. Nestled among forested hills and flowing rivers, Tsumago offers an authentic window into rural Japan. After exploring, we transfer and we’ll unwind in the onsen before a multi-course dinner with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 8 km (5 mi), 4 hours
Elevation: +200 m (660 ft), -380 m (1,250 ft)
Terrain: Forest and countryside trails, stone paths, asphalt sections
Accommodation: Taoya Kisjo Hotel Tsumago

Flexible hike option: 2.5 km (1.6 mi) from Magome-juku to Magome Pass or 5.5 km (3.4 mi) from Magome Pass to Tsumago

After breakfast, we farewell our accommodation and transfer to Nagiso to begin today’s walk. The trail follows the Yogawamichi Path from Modono to Nojiri, a scenic route that avoids the busy riverside road. This captivating walk meanders through unspoiled countryside, serene alpine forests, and traditional mountain villages, offering an authentic glimpse into rural life in the Kiso Valley. As we ascend through dense cedar forests, filtered light reveals glimpses of distant peaks and valleys below. The path combines natural beauty with cultural depth, embodying the quiet spirit of Japan’s ancient travel routes. After the walk, we meet our driver and continue to the charming town of Kiso-Fukushima. In the early evening, there’s an optional visit to a local sake brewery to meet the friendly staff and sample regional varieties before enjoying a traditional dinner with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 13 km (8.1 mi), 5 hours
Elevation: +669 m (2,195 ft)
Terrain: Steep sections, stone paths, wooden footbridges, dirt trails
Accommodation: Tsutaya Inn, Kiso Fukushima

Flexible hike option: 10 km (6 mi) from Nenoue Pass to Nojiri, 3.5-4 hours, -500 m (1,640 ft)

After breakfast, we travel through the mountainous landscapes of southeast Nagano, transferring to the base of Mt. Ontake to begin today’s walk. This trail—often described as one of Japan’s most captivating—begins with a steep stone staircase ascending through dense forest to the monument of the Three Great Gods of Ontake, known as Omata Sansha. The path continues through lush woodland, passing sacred Reijinhi stone carvings used in ancient rituals. Along the way, we visit Hanadofukando and Juni Gongen Shrines before reaching Shintaki Falls, a 50 m (164 ft) cascade revered for its purification ceremonies. Pilgrims have long journeyed here to cleanse both body and spirit. The final stretch leads to Kiyotaki Falls, another sacred site framed by mossy rocks and serene forest. After the walk, we transfer to Tsutaya Tokinoyado Retreat to relax in the open-air onsen before a delicious dinner with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 6 km (3.7 mi), 4–5 hours
Elevation: +250 m (820 ft), -250 m (820 ft)
Terrain: Stone paths, steep staircases, dirt forest trails
Accommodation: Tsutaya Tokinoyado Retreat

Flexible hike option: 4-5 km (2.5-3.1 mi), 3 hours, +150 m (492 ft), shorter section Ontake Waterfall Trail loop

After breakfast, enjoy the views of Mt. Ontake before setting out on today’s walk. The journey from Yabuhara to Narai via Torii Pass feels like stepping back in time through the heart of the Kiso Valley. The trail winds through tranquil forests where sunlight filters through the canopy, occasionally revealing wooden torii gates marking progress toward the pass. As we ascend, the scenery opens to sweeping views of the Kiso Valley, dotted with traditional villages nestled among the mountains. Arriving in Narai, a beautifully preserved post town, we’re greeted by cobblestone streets, Edo-era architecture, and the timeless charm of old Japan. After the walk, enjoy time to explore Narai at your own pace before continuing to the picturesque town of Karuizawa. Our accommodation tonight is at the elegant Ancient Hotel, a luxurious woodland retreat with soothing hot springs. Dinner is served with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 7 km (4.3 mi), or you can skip the whole day of hiking and transfer to Narai
Elevation: +373 m (1,224 ft)
Terrain: Forest trails, stone paths, dirt tracks, moderate inclines
Accommodation: Ancient Hotel, Karuizawa

Flexible option: Transfer directly to Narai and spend the day at leisure

After a hearty breakfast at the Ancient Hotel Karuizawa, we set out on a gentle morning walk to Shiraito Waterfalls, where delicate streams cascade over a wide rock face like silken threads. After a peaceful moment to reflect, we transfer to the historic Usui Pass to begin our final and most rewarding walk of the journey. Here, we trace a quiet section of the old Nakasendō Trail, once traveled by samurai and merchants, beginning at the Kumanokotai Shrine on the border of Nagano and Gunma Prefectures. The trail descends steadily through shaded cedar forests, past moss-covered stone markers and remnants of Edo-era rest stations, revealing expansive valley views along the way. This 8 km descent is both scenic and deeply atmospheric—a perfect finale to our walking adventure. In the afternoon, we travel by private transfer back to Tokyo, concluding our journey at the Royal Park Hotel Shiodome.

Meals: Breakfast, lunch
Hiking: 8 km (5 mi), 3.5 hours
Elevation: -750 m (2,460 ft)
Terrain: Cypress-lined forest trails, stone paths, dirt tracks, steep descents

Flexible hike option (morning): 2.5 km (1.6 mi), 1–2.5 hours, Ancient Hotel to Shiraito Waterfalls via Ryugaeshi Falls