Experience the tranquil magic of a Japanese winter during this immersive eight-day itinerary. Starting in Kyoto, you'll head to the snowy Kiso Valley to hike along the ancient Nakasendo Trail, spending each night in quaint wooden villages or hot spring inns. After a week spent savoring regional cuisine, snowshoeing through cedar forests, and soaking in natural mineral pools, you'll enjoy your final night in the hustle and bustle of Tokyo—the historical endpoint of the trail.


  • Marvel at the beauty of winter in the scenic Kiso Valley
  • Hike in the footsteps of Samurai on the ancient Nakasendo Trail
  • Stay in historic, family-run country inns
  • Soak in natural hot springs and mineral pools
  • Sample wonderful regional and seasonal cuisine

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Kyoto Kyoto
Day 2 Trek from Nakatsugawa to Magome Magome
Day 3 Magome to Tsumago Tsumago
Day 4 Tsumago, Nagiso & Kiso-Fukushima Kiso-Fukushima
Day 5 Kiso-Fukushima to Narai Narai
Day 6 Narai, Kiso-Hirasawa & Asama Onsen Matsumoto
Day 7 Train to Tokyo Tokyo
Day 8 Depart Japan  

Detailed Itinerary

Day 1: Arrive in Kyoto

Snowfall over Kyoto's Golden Temple.
Snowfall over Kyoto's Golden Temple.

Welcome to Japan! Arrive in the historic imperial capital of Kyoto, the official starting point of the Nakasendo Trail. Settle into your accommodation, then spend the afternoon getting to know this exquisite city of gardens, temples, and palaces. 

Day 2: Trek from Nakatsugawa to Magome

Ancient cobbled paths through Magome.
Ancient cobbled paths through Magome

Your first day begins in Nakatsugawa, one of many historic post towns along the Nakasendo Trail. This vital artery was known as the "road through the mountains" and linked Kyoto to Tokyo during Japan's feudal period. Along the route were 69 post towns where weary travelers could rest before continuing on to the next leg.

Start your walk from the town's charming main street, which still retains its Edo-period heritage with traditional sake shops and historic shopfronts. You'll pass through the next village of Ochiai before ascending through dense cedar forests, walking a path paved with cobbles that date back to the 18th century. End your day in the beautifully preserved post town of Magome, where you'll settle into a local inn for the night.

Walking distance:  5.2 miles (8.3 km)
Walking duration: 3 hours

Day 3: Magome to Tsumago

Welcoming locals along the Nakasendo Trail.
Welcoming locals along the Nakasendo Trail

From Magome, you'll walk to Tsumago via one of the prettiest and best-preserved portions of the Nakasendo Trail. You'll likely encounter snow over the Magome Pass, with sweeping views across the frozen forests. You'll arrive in Tsumago around lunchtime, where you can sample the local delicacy of gohei-mochi, skewered sticky rice glazed in a sweet paste of miso, sesame, and walnuts. Tsumago is a living museum that is still home to residents whose families have lived here for generations. The afternoon is yours to explore the many small shops along the picturesque main street and get settled into your local inn. 

Walking distance: 5.2 miles (8.3 km)
Walking duration: 3 hours

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Day 4: Tsumago, Nagiso & Kiso-Fukushima

Winter hiking along the Nakasendo Trail.
Winter hiking along the Nakasendo Trail

Day three continues your exploration of Tsumago, including a visit to the enjoyable Edo-era Wakihonjin Museum. Today's walk is a short but pleasant stroll from Tsumago to Nagiso along quiet country lanes. From Nagiso, you'll hop on a local train for the brief journey to Kiso-Fukushima, a delightful post town that was once an important Sekisho (ancient customs checkpoint) on the Nakasendo.

Stroll through the village before heading out to a comfortable ryokan on the outskirts of the community. Traditional ryokan (traveler's hot-spring inns) pride themselves on their excellent cuisine and indoor and outdoor thermal baths—the perfect way to soothe tired feet and warm up on a winter evening.

Walking distance: 2.3 miles (3.7 km)
Walking duration: 1 hour

Day 5: Kiso-Fukushima to Narai

Traditional gates at the top of the Torii Pass.
Traditional gates at the top of the Torii Pass

Your fourth day takes you on a short train journey to Yabuhara, where you'll set off on foot to cross the scenic Torii Pass. This section is likely to have the deepest snow of the trip, and you'll have the option of switching to snowshoes. Red cedar forest and ancient, moss-covered statues mark the highest point of the journey, where you'll start your descent to the atmospheric village of Narai. You'll arrive with plenty of time to explore Narai's preserved 18th-century main street and have lunch at one of the small local restaurants. Settle into one of the town's cozy family-run inns for the evening.

Walking distance:  3.9 miles (6.2 km)
Walking duration: 3 hours

Day 6: Narai, Kiso-Hirasawa & Asama Onsen

The 17th-century Matsumoto Castle.
The 17th-century Matsumoto Castle

Your final day on the Nakasendo Trail starts with a short stroll from Narai to Kiso-Hirasawa, a town known for its locally-produced lacquerware. Watch the craftsmen at work and pick up some souvenirs before boarding a train for Matsumoto. This elegant small city is nestled in the central Alps region and is known for its stunning 17th-century castle. After a quick tour of the imposing fortress, you'll make your way to nearby Asama Onsen for the evening. With a history dating back 1,300 years, this spa town is home to one of the most authentic Ryokan inns in the region, with mineral-rich steam pools and intricate wooden architecture from the Meiji era.

Walking distance: 1.6 miles (2.5 km) 
Walking duration: 1 hour

Day 7: Train to Tokyo

Nightfall at the Hama-Rikyu Gardens, Tokyo.
Nightfall at the Hama-Rikyu Gardens, Tokyo.

After breakfast, bid the quiet beauty of the Kiso Valley farewell, hopping on a train to Tokyo for your last evening in Japan.

After settling into your accommodation, take an afternoon walking tour of Tokyo, starting at the Hama-Rikyu Gardens. Wander the extensive grounds and enjoy the striking contrast between the lush gardens and the gleaming towers of the modern Shiodome business area beyond. Next, you'll pay a visit to Nihonbashi (the "Japan Bridge"). Considered the official center of the country and the zero marker point for all main roads since the Edo period, it marks the traditional end of the Nakasendo Trail.

Day 8: Depart Japan

Sunrise over Tokyo's Chureito Pagoda.
Sunrise over Tokyo's Chureito Pagoda.

Today you'll make your way to the airport for your departing flight.

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Map of Winter on the Nakasendo Trail: Kyoto, Kiso Valley & Tokyo - 8 Days
Map of Winter on the Nakasendo Trail: Kyoto, Kiso Valley & Tokyo - 8 Days