After earning absolute power over Japan’s feuding factions, Tokugawa Ieyasu became the island nation’s first shogun, and in the early 17th century he consolidated his political control in Edo—now Tokyo—away from the emperor’s longtime residence in Kyoto. A walking highway was quickly developed with 69 resting stations; the Nakasendo—which translates to “Central Mountain Route”—allowed dignitaries, from samurai to philosophers, to travel between the country’s two most important strongholds via a series of navigable alpine passes.
Today, as Japan continues to break tourism records, charting higher and higher numbers of international travelers each month, this old road has found new relevance not as the important transit artery it once was, but as the perfect slow-travel alternative to the whirr of the bullet train that zips throngs of travelers from Tokyo to Kyoto.
Here, we’ve distilled the 330-mile walking trail down to its most compelling highlights—from unmissable half-day hikes through snow-capped vistas and charming villages, to evenings at some of the best accommodation, both traditional and contemporary, in the country. Consider this your CliffsNotes guide to exploring some of Japan’s most easily accessible off-the-beaten-path experiences—all with a luxurious twist, of course.
Day 1: Karuizawa
Depart Tokyo aboard the Hokuriku Shinkansen (bullet train), and in 90 minutes you’ll reach Karuizawa, the Hamptons of Tokyo, where the city’s elite retreat to their forested chalets, be it to escape the summer heat, or to come skiing on wintery weekends. After perusing the vast assortment of premium shopping—from Burberry to Beams—surrounding the train station, hop in a cab to reach Shishi-Iwa House, your home for the night. The hotel’s rooms are spread across three distinct architectural expressions—two playful designs by Shigeru Ban, and a third more traditional construction by Ryue Nishizawa (of Pritzker Prize-winning SANAA fame)—set among a quiet neighborhood of country estates. Our favorite is House No. 3 (Nishizawa’s), which riffs on a traditional temple construction and is covered in fragrant hinoki wood. At the on-site restaurant, Shola (in House No. 2), seasonal ingredients sourced in the hills and valleys around Karuizawa are stitched into wildly creative dishes that combine Japanese and French cooking methods.
Day 2: Matsumoto
In the morning, walk down the street to soak in the mineral-rich waters at the Hoshinoya Resort’s high-end onsen before making your way back to the train station for another 90-minute ride to the small city of Matsumoto. Once an important feudal stronghold deep in the Japanese Alps, Matsumoto is known today for its towering castle; arguably the most stunning fortification in the entire country with its black-onyx trim and turquoise moat filled with curious koi. In the evening, check in to Tobira Onsen Myojinkan, a ryokan inn tucked away in a small forest just beyond the city. True to its Relais Châteaux accreditation, the property excels at dinnertime—its multi-course, intricately crafted kaiseki dishes honor the regional bounty and pair with the finest local sake, all brewed using pure alpine water.
Day 3: Narai-juku
It’s a quick 45-minute train ride along the snaking Narai River from Matsumoto down to Narai-juku, one of the best-preserved resting stations from the Nakasendo’s bygone era of popularity. A cluster of rickety wooden houses line the little town along a single road from one end to the other, and are filled with an assortment of antique shops and soba noodle restaurants. Your accommodation for the evening is Byaku Narai, an inn which has taken over a scatter of traditional timber structures in town and turned them into stunning suites that blend old-school Japanese architectural elements with subtle modern twists—most rooms have a private outdoor hot tub. Housed in a former storehouse of a once-thriving sake brewery, the hotel’s restaurant, Kura, offers nightly eight-course meals where the honest, simple flavors of the local ingredients are highlighted through minimally invasive recipes.
Day 4: The Kiso Valley
Wake up early in the morning and take the local train one short stop to the village of Yabuhara. From here you’ll embark on a two-hour hike that will take you through one of the most stunning mountain passes in central Japan, the Torii Pass, where, famously, an old warlord prayed to the Shinto god of Mt. Ontake for victory in an upcoming battle. A beautiful gate—a torii—was constructed here after the battle was won, and it still stands today, with snowy views of Mt. Ontake in the distance. The Nakasendo Trail will wind you back down into Narai-juku, where you can continue up the river valley to a couple of the other former resting posts including Niekawa, home to several lacquerware artisans. Hop on the train once again for a 90-minute ride to Nakatsugawa. Here, one of the six cottages at Nagataki is home for the night—the ryokan with its shoji paper walls and woven tatami flooring counts emperor Akihito among its long list of esteemed guests.
Day 5: Magome-juku
A short taxi ride will take you to the most popular stretch of the entire Nakasendo—the half-day hike between the two well-preserved resting posts of Tsumago-juku and Magome-juku. You can walk them in either direction, though most people prefer to start in Magome-juku as the trail slightly inclines in a downward fashion back towards Tsumago-juku. Along the way, you’ll pass dozens of Shinto shrines dedicated to the deities of the valley’s rivers, mountains and trees, as well as an assortment of adorable mom-and-pop-run minshuku—no-frills inns. The highlights are the two traditional villages themselves, where at every turn it feels as though you’ve stepped onto the set of FX’s Shogun. From here, it’s a two-hour train ride back into modern times, and to the sprawling metropolis of Nagoya where you can hop back on the bullet train for a short zip to Kyoto.
