Begin your self-guided cycling adventure in the charming post town of Matsuida, at the foot of the legendary Usui Pass. Receive a bicycle, route briefing, and local insights before setting off on a full-day journey.

Cycle along quiet backroads through beautiful rural landscapes to the beautifully preserved post town of Sakamoto-juku, once an important stop for travelers during the Edo period. Continue climbing the historic Usui Pass, famous for its spectacular mountain scenery and remarkable engineering heritage, before descending into the elegant mountain resort town of Karuizawa.

Along the way, experience historic villages, old stone pavements, shrines, tea houses, and panoramic views that most visitors to Japan never discover. Your kickstart briefing includes route navigation, historical highlights, recommended cafés and lunch stops, safety information, and local recommendations, allowing you to explore at your own pace while gaining a deeper appreciation of the Nakasendo’s rich history.

We use a special RideWithGPS Experience Program that allows you to load onto any smartphone (Android or Iphone) at no cost! This provides turn-by-turn navigation as well as a written guide to many POI's and important sections. (https://ridewithgps.com/experiences)

In addition we have created the route using an extremely accurate GPS system that allows navigation through even the tiniest of paths, roads and byways.