Perfect for active walkers, this trip combines a four-day walk on Japan's Nakasendo Trail, which connected Tokyo and Kyoto during the days of shoguns and samurai, with a visit to three historic Japanese capitals, Tokyo, Nara, and Kyoto. You'll begin your trip in Tokyo, then take to the trail and stay in post towns once used as feudal-era stopover points.  You'll visit UNESCO World Heritage Sites in Nara, Yoshino, and Mount Koya, then spend two nights in Kyoto, where geisha still entertain well-heeled guests and Buddhist temples beckon.


  • Spend four days walking the Nakasendo Trail, visiting samurai-era post towns
  • Visit Nara, Japan's first permanent capital, and discover its temples and gardens
  • Explore Mount Koya's Okunoin Cemetery and stay at a Buddhist monastery
  • Discover Kyoto's geisha district and world-famous temples

Brief Itinerary

Day Highlights Overnight
Day 1 Meet in Tokyo Tokyo
Day 2 Sightseeing in Tokyo Tokyo
Day 3 Nakasendo Trail from Kiso-Hirasawa to Narai Narai
Day 4 Narai to Kiso-Fukushima Kiso-Fukushima
Day 5 Kiso-Fukushima to Tsumago Tsumago
Day 6 Nakasendo Trail and Nara Nara
Day 7 Nara Nara
Day 8 Yoshino Yoshino
Day 9 Mount Koya Mt Koya
Day 10 Transfer to Kyoto Kyoto
Day 11 Kyoto Kyoto
Day 12 Tour ends  

Detailed Itinerary

Day 1: Meet in Tokyo

Cherry Blossoms and Pagoda in Tokyo's Ueno Park
Cherry Blossoms and Pagoda in Tokyo's Ueno Park

Meet your guide at the hotel in the evening, then enjoy a welcome dinner for the group at a nearby restaurant.

Day 2: Sightseeing in Tokyo

Tokyo's Harajuku District at Night
Tokyo's Harajuku District at Night

Today you'll take a walking tour of Tokyo, starting at Nihonbashi (the "Japan Bridge"). This bridge has served as the zero marker point for Japan’s main roads since the Edo period. Afterward, visit Ueno and the Tokyo National Museum to see exhibits dating from the Edo era, the heyday of the Nakasendo Trail. (If the Museum is closed, you will visit the Kappabashi restaurant supply district, famous for its kitchenware and for the plastic models of food used in Japanese restaurant displays.) Continue on to the Meiji Jingu, the shrine dedicated to Emperor Meiji, and then to the fashionable Harajuku district. In the evening your tour guide will offer suggestions for restaurants.

Day 3: Nakasendo Trail from Kiso-Hirasawa to Narai

Traditional Wooden Buildings in Narai, Japan
Traditional Wooden Buildings in Narai, Japan

Your travels through rural Japan begin with a trip to the remote Kiso Valley. Over the next three days, you'll walk from village to village, staying in ryokan and minshuku, two types of small, family-run lodgings.  Today, enjoy a lunch of buckwheat noodles in the town of Shiojiri, then walk from Kiso-Hirasawa to Narai. Kiso-Hirasawa is known for its lacquerware; you may have a chance to see craftsmen at work. Tonight you'll stay in Narai, a well-preserved post-town, in an atmospheric traditional minshuku.

Walking distance: 1.6 miles/2.5 kilometers 
Elevation gain: negligible ascent and descent
Duration: 1 hour

Day 4: Narai to Kiso-Fukushima

Tranquil Garden in Kiso-Fukushima, Japan, Courtesy of Shutterstock
Tranquil Garden in Kiso-Fukushima, Japan, Courtesy of Shutterstock

On your second day on the Nakasendo Trail, you'll walk from Narai to Yabuhara via the Torii Pass and continue by train to Kiso-Fukushima. You'll stay in a traditional ryokan with its own natural hot spring. Soak in an indoor bath made from cypress wood or try the outdoor baths surrounded by trees.

Walking distance: 3.9 miles/6.2 kilometers
Elevation gain: 885 feet/270 meters ascent; 1,128 feet/344 meters descent
Duration: 3 hours

Day 5: Kiso-Fukushima to Tsumago

Traditional Wooden Building in Tsumago, Japan
Traditional Wooden Building in Tsumago, Japan

Travel from Kiso-Fukushima to Nojiri by train, then take a short taxi ride to the Nenoue-Toge Pass. You'll walk along a tranquil section of the Nakasendo Trail through small settlements and rice fields to Tsumago or to the nearby hamlet of O-Tsumago. Just a few decades ago, Tsumago was falling into disrepair, but the residents saved and restored the town. They adopted strict rules that prohibit the sale, rental, or demolition of Tsumago's historic houses. Tsumago is a living museum that is still inhabited by the local residents. 

Walking distance: 8.7 miles/14 kilometers
Elevation gain: 1,129 feet/344 meters ascent; 2,275 feet/723 meters descent
Time required: 4.5 hours

Day 6: Nakasendo Trail and Nara

Nakasendo Trail in Magome, Japan
Nakasendo Trail in Magome, Japan

Today you'll walk from Tsumago to Magome, your last stop in the Kiso Valley. The route from Tsumago to Magome is the best-preserved part of the Nakasendo Trail. Enjoy lunch in Magome and explore the many small shops along the main street. You might also try gohei-mochi, skewered sticky rice covered in a sweet paste of miso, walnuts, and sesame. After lunch, you'll travel by local train and shinkansen (bullet train) to Nara.

Walking distance: 5.2 miles/8.3 kilometers
Elevation gain: 1,410 feet/430 meters ascent; 1069 feet/326 meters descent
Time required: 3 hours

Day 7: Nara

Buddha in Daibutsu-den, Nara, Japan
Buddha in Daibutsu-den, Nara, Japan

Enjoy a guided walk in Nara this morning. Some of Japan’s greatest cultural treasures are concentrated in and around Nara, including eight UNESCO World Heritage Sites. Many of these sites are in or near Nara Park, home to a thousand or more free-roaming deer.  You'll visit two World Heritage Sites on your walk, Kasuga Taisha Shrine and Todaiji temple. Todaiji's Daibutsu-den is the largest wooden building in the world, built to house a 53-foot (16-meter) bronze and gold image of the Rushana Buddha. Afterward, you'll have some free time to relax, visit a garden or wander through the old town.

Day 8: Yoshino

Cherry Blossoms in Yoshino Park, Japan
Cherry Blossoms in Yoshino Park, Japan

From Nara, you'll travel to the ridge-top village of Yoshino and stay in a comfortable ryokan. Yoshino is a UNESCO World Heritage Site, one of the most famous places in Japan for viewing springtime cherry blossoms. You'll visit Yoshimizu Shrine, which is associated with Minamoto no Yoshitsune, Emperor Godaigo, and Toyotomi Hideyoshi, and explore the area.

Day 9: Mount Koya

Okunoin Cemetery on Mount Koya, Japan
Okunoin Cemetery on Mount Koya, Japan

Take the scenic train to Mount Koya, high in the mountains of the Kii Peninsula. Since the 9th century, Mount Koya has been a place of religious devotion and ceremony. Today there are more than 100 monasteries, many of which offer shukubo (temple lodgings). Visit the Kongo-buji temple and walk through the vast Okunoin Cemetery, Japan's largest. Tonight you will stay in a shukubo and dine on shojin-ryori Buddhist vegetarian cuisine.  Tomorrow morning, you can rise early and join the Buddhist morning service if you wish.

Day 10: Transfer to Kyoto

Maiko and Geiko Walking in Kyoto, Japan
Maiko and Geiko Walking in Kyoto, Japan

Today you'll take the train to Kyoto and check into your hotel. Kyoto was Japan’s capital for centuries and is still considered to be the country’s cultural heart. In the evening, take a walk in Gion, Kyoto’s geisha district. You may have an opportunity to see a geiko (fully-fledged geisha) or maiko (apprentice geisha) walking on Gion's narrow streets.

Day 11-12: Kyoto - Depart

Aqueduct at Nansenji Temple, Kyoto, Japan
Aqueduct at Nansenji Temple, Kyoto, Japan

On your morning guided walking tour, you'll visit the Sanjo-ohashi Bridge, which marks the western end of the Nakasendo Trail. You'll continue to Nanzenji, a peaceful 13th-century Zen Buddhist temple. Stroll along the Philosopher’s Path beside the waters of a small canal. The path, which is lined with craft shops, cafés, temples, and shrines, ends near Ginkakuji, the Silver Pavilion. You'll have free time in the afternoon to explore or shop. In the evening, enjoy a farewell dinner with your guide. 

After breakfast at the hotel in Kyoto, your tour comes to an end. Your guide will be available to offer assistance and advice for traveling to the airport to catch a flight and for onward travel if you plan to extend your stay in Japan.


Map of Nakasendo Trail: Tokyo to Kyoto - 12 Days
Map of Nakasendo Trail: Tokyo to Kyoto - 12 Days