5 Day Nakasendo Walking Tour

Classic Inn to Inn ✦ 5 days self-guided ✦ Leisurely ✦ From $1815

Walk the Paths of Ancient Japanese Emperors

Step back in time and walk the storied Nakasendo Trail, an ancient route weaving through Japan’s central mountains. This five-day self-guided adventure takes you along forested paths and cobbled village streets, connecting the historic post towns that once served weary travelers during the Edo period. Experience the charm of well-preserved towns like Magome, Tsumago, and Narai, where traditional wooden inns, stone pathways, and gentle lantern-lit evenings transport you to centuries past.

Beyond the history, this journey is a feast for the senses—enjoy breathtaking views of the Kiso Valley, unwind in soothing onsen hot springs, and savor exquisite kaiseki-style cuisine at family-run ryokan and minshuku. Whether admiring Matsumoto Castle’s towering elegance or wandering through lacquerware shops in Kiso-Hirasawa, each day offers an intimate glimpse into Japan’s rich culture and stunning landscapes. With seamless train connections, detailed maps, and our expert support, this is the perfect blend of exploration, relaxation, and cultural immersion. Lace up your walking shoes and embark on a journey through Japan’s living history!

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5 Day Nakasendo Walking Tour
rides: 30 to 65 kms
sleep: boutique inns
eat: best regional cuisine

Go Private
This tour is only available as a Private Date. Spring & Fall are the best for walking.

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Download a detailed itinerary with route profiles & more, to read and share with friends.

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Japan walking tour day by day details

day 1: Walk Through Time – Magome to Tsumago

Scenic hike over Magome-tōge Pass
Explore the historic post town of Tsumago
Stay at a charming family-run minshuku

Arrive via Japan’s world-famous bullet train before setting off on your first walk from Magome to Tsumago. This well-preserved Edo-period post town invites you to stroll along its stone-paved streets, admiring wooden merchant houses and waterwheels. Settle into a cozy minshuku, where a home-cooked Japanese dinner and a quiet evening in a yukata gown await.
Walk: 3 hours, Land: hilly
Eat: Dinner
Sleep: Minshuku*

day 2: Bamboo Forests & Mountain Passes – Tsumago to Nojiri

Hike through serene cedar and bamboo forests
Explore Kiso-Fukushima, a historic post town
Indulge in a kaiseki feast at an onsen ryokan

Today’s trail leads you through some of the Nakasendo’s most untouched scenery, winding through small valleys and towering cedar groves. Arriving in Kiso-Fukushima, a town once pivotal to the region’s trade, you’ll unwind at a traditional onsen ryokan, enjoying a rejuvenating soak and a multi-course kaiseki dinner.
Walk: 20 mi / 35 km, Land: hilly
Eat: Breakfast, Dinner
Sleep: Onsen Ryokan*

day 3: Torii-tōge Pass & Lacquerware Traditions – Yabuhara to Narai

Cross the scenic Torii-tōge Pass
Discover Narai’s beautifully preserved Edo-era streets
Visit Kiso-Hirasawa’s renowned lacquerware artisans

After a short train ride, you’ll set off over the Torii-tōge Pass, where panoramic mountain views await. Wander through Narai, one of the Nakasendo’s best-preserved post towns, before continuing to Kiso-Hirasawa, famous for its exquisite lacquerware craftsmanship. Tonight’s accommodation offers a warm, traditional welcome with another delicious Japanese meal.
Walk: 20 mi / 35 km, Land: hilly
Eat: Breakfast, Dinner
Sleep: Minshuku*

day 4: Matsumoto Castle & Scenic Journey to Karuizawa

Visit the iconic Matsumoto Castle
Explore charming streets and historic sites
Unwind in a traditional inn in Karuizawa

Enjoy a leisurely morning in Matsumoto, home to Japan’s oldest surviving castle, before continuing to your final stop in Karuizawa or Komoro. These elegant resort towns offer a blend of history and natural beauty, perfect for an evening of relaxation in a ryokan with fine Japanese baths and regional cuisine.
Walk: 20 mi / 35 km, Land: hilly
Eat: Breakfast, Dinner
Sleep: Ryokan*

day 5: Usui-tōge Pass & Farewell to the Nakasendo

Hike the breathtaking Usui-tōge Pass
Descend into the picturesque Yokokawa valley
Return to Tokyo via the bullet train

Your final walk takes you over the Usui-tōge Pass, one of the Nakasendo’s most scenic sections. Descend through lush forests to Yokokawa, where you’ll board the train for your journey back to Tokyo. Arrive in the capital in the late afternoon, carrying memories of Japan’s timeless landscapes and rich traditions.
Walk: 5 hours, Land: hilly
Eat: Breakfast

*The inns in the villages are very small with just a few rooms. The names of inns used for your trip will be included in your confirmation information.

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Whatcha gonna get

Handpicked lodges, double occupancy
Daily breakfast*
Dinners featuring fine local cuisine*
Comprehensive route notes
Topographic maps
Local support by phone
Train and bus travel*

*as noted in itinerary

note: Daily transfer of luggage is not included, but can be arranged once on the trail.

Getting there

Guests walking can select to start from either Kyoto or Tokyo. The trip finishes in Tokyo. Train tickets via either Kyoto or Tokyo are included, but no airport transfers within either city.

Guests should plan their flights to arrive in Japan the day before (or earlier) and onward travel the day after your walking trip ends.

Tokyo airports: Narita Airport code: NRT
Haneda Airport code: HND
Local Time: GMT+9

Travel Tip: Kyoto can be reached easiest by flying to Osaka Kansai (KIX), then by train to Kyoto.

Documents Please

Got your passport ready? You'll need it for this adventure! Some travelers may also need a visa for Japan — be sure to check with the nearest embassy so you can focus on the fun, not the paperwork.

Good Sleep

Our Nakasendo trip features a number of nights in traditional, historic inns either minshuku or ryokan. These inns orginated back in the era of when the emperors and their courts walked from palace to palace and these inns sprung up along the trails to accommodate the parties.

Arriving at a ryokan is an experience in itself. The hostess, okami , dressed in a kimono, comes to welcome the guests. Once you take your shoes off , put on the slippers made available at the entrance. An employee, still in a kimono, then comes to take over from the okami and accompany the customers to their room.

Good Eats

Always ranked in the top ten of cuisines worldwide, Japanese food is a delight both visually and for its taste. Dinners at the minshukus and ryokan on this tour are traditional Kaiseki Ryori, with many small dishes of vegetables, fish, meats and more.

A typical dinner could consist of: shiizakana (appetizers served with Japanese sake),mukouzuke (sashimi – slices of raw fish), kuchitori (a small side dish), suimono (a soup), nimono (simmered vegetables), kounomono (Japanese pickles), yakimono (grilled fish) and more.