No time machine, no problem! The 8-day Nakasendo Trail cycling trip will take us back to 17th century Japan, retracing the steps of samurai warriors, merchants, pilgrims, and other travelers moving between Kyoto, the Imperial Japanese capital and Edo (Tokyo), the political capital of the time. We’ll stroll through historical post towns, feel the serenity of bamboo groves, marvel at centuries-old shrines and temples, and spend nights in traditional minshuku and ryokan. This will be an adventure to remember!
The Nakasendo Trail is more than just a cycling adventure—it’s a step back in time, a week-long journey to the Japanese Edo period, with well-preserved reminders along the trail. You will visit some of the most important and most beautiful post towns on the route, including Tsumago and Magome among many others. The rest of the cycling tour goes through serene woodlands, cobblestoned paths meandering through the mountains, remote villages, and a myriad of other landscapes. Join this guided journey and prepare for a total immersion into the Japanese Edo period, its culture, traditions, and its food.
The itinerary is just a sample—it is not set in stone, and neither are the daily distances, but you can expect to ride in these areas. Every tour is tailored to each guest’s riding style and preferences. While the general regions stay the same, the exact destinations vary to create a truly bespoke experience.
This day is all about arriving to the guide’s base for orientation and a bike fitting. You can arrive from 10 am onwards so we have plenty of time to get bikes prepped. We’ll also go on a short orientation ride.
Meals: Dinner
Accommodation: Guide’s base or similar
Nagawa sits in the Nagano highlands, mixing rolling farmland, forested slopes, and cool alpine air. Riders can expect quiet rural roads, gentle valley stretches, steady climbs, and wide mountain views, with historic post-town remnants, clear rivers, and open plateaus adding scenic variety.
Meals: Breakfast, lunch, dinner
Accommodation: Traditional Japanese minshuku, ryokan or a modern resort hotel
The Suwa/Shiojiri area blends lakefront views, vineyard-covered hills, and forested mountain passes. Expect smooth riding around Lake Suwa, gentle vineyard slopes near Shiojiri, and occasional steeper climbs into surrounding highlands, with shrines, hot springs, and small craft villages adding local charm.
Meals: Breakfast, lunch, dinner
Accommodation: Traditional Japanese minshuku, ryokan or a modern resort hotel
The Kiso area runs along a dramatic wooded valley framed by steep mountains, with serene rivers, deep forests, and stretches of the historic Nakasendō. Expect shaded roads, moderate climbs, and scenic gorges, with traditional post towns and old cedar-lined paths adding a timeless, atmospheric feel.
Meals: Breakfast, lunch, dinner
Accommodation: Traditional Japanese minshuku, ryokan or a modern resort hotel
The Ochiai/Nakatsugawa area follows the lower Kiso Valley, mixing riverside stretches, wooded hills, and sections of the old Nakasendō. Expect mellow valley riding with a few short climbs, historic post towns, stone-paved trails, and viewpoints overlooking terraced villages and forested ridges.
Meals: Breakfast, lunch, dinner
Accommodation: Traditional Japanese minshuku, ryokan or a modern resort hotel
The Inuyama area offers gentle riverside terrain along the Kiso River, framed by low hills and castle views. Expect smooth, easy riding past shrines, old merchant streets, and Inuyama Castle’s iconic perch above the water, with quiet country roads leading into small villages and wooded backroads.
Meals: Breakfast, lunch, dinner
Accommodation: Traditional Japanese minshuku, ryokan or a modern resort hotel
The Hikone area sits along the shores of Lake Biwa, offering flat lakeside routes with wide open views and breezy waterfront paths. Expect easy riding through historic castle districts, peaceful rice fields, and traditional neighborhoods, with Hikone Castle providing a standout cultural landmark.
Meals: Breakfast, lunch, dinner
Accommodation: Traditional Japanese minshuku, ryokan or a modern resort hotel
The final day brings an afternoon arrival in Kyoto, where the ride transitions into a relaxed city welcome. Expect a gentle shift from countryside scenery to temple-lined streets, historic districts, and riverside paths, with time to settle in and enjoy Kyoto’s calm, traditional atmosphere.
Meals: Breakfast, lunch, dinner
Very highly recommended. Tim has great bikes and excellent local knowledge. I spent one night before a good early breakfast and then headed out for a loop as recommended by Tim which was the best 80kms I’ve ever cycled. Stunning scenery, beautiful ancient shrines, epic climbs on deserted roads and awesome food stops.
Included:
Add-ons (possible to arrange at an additional fee, leave us a note at checkout):
Not included:
Participants should be comfortable sustaining 4-6 hours of moderate physical activity per day. While e-assist bikes are available and significantly reduce the effort required on climbs, they don’t replace the need for basic riding skills and day-to-day endurance. Tbe average riding pace is around 15 km/h.
Please let us know in advance about any medical conditions or limitations that could affect your participation. We’ve welcomed riders of all ages—from 12 to 80 years old—and from many different backgrounds and fitness levels. While this is a challenging experience and not suited to everyone, your guides work hard to make each day as comfortable, supportive, and achievable as possible for every participant.
Here’s what you’ll need:
Touring in Japan covers mountains, plains, and coastal areas, where rain is not uncommon. Weather in the winter can also get quite cold in the winter. Make sure to bring clothing appropriate for the season. Generally, pack light and use layers. Due to high humidity, a waterproof hardshell is great and effective as any membrane shell. High-quality Merino fabric base layers as well as high-quality bib or riding shorts are strongly recommended. You’ll be able to do laundry in most lodgings so you might not need as much clothing as you think.
All attendees should have their own smartphone device with local data provisioning (e-Sim or similar).
If you’re bringing your own bicycle or equipment, you will be 100% responsible for any spare parts, repairs, damages or losses. Your en-route guide is equipped for most mechanical issues, but they do not carry spares for bikes other than their own. Read more about this in the next question.
Rental bikes
High-end conventional bikes or e-bikes typically featuring 1×11 or 2×11 wide range components are included in the price of the tour. You also get a repair kit (pump, tool, patches, etc.), safety lights, and “rinko” bags for the train. Helmet, rental clothing or shoes are not provided. If you bring your own saddle and/or pedals, they will be installed for you. Please do not bring racks, panniers, or other components without consulting first. Rental bikes are suitable for bikepacking type saddle bags, frame bags, or front, and not old-school expedition racks and panniers.
Your own bike
While we encourage participants to use our bikes for convenience, you’re more than welcome to bring your own. Mechanics on the tour will service all bikes and carry out repairs where possible to keep everything running smoothly throughout the trip. There’s no additional charge or discount for bringing your own bike—everyone receives the same level of support.
Please note that transporting large luggage and bikes in Japan can sometimes be challenging, especially to and from airports. Using your guides’ bikes is often the easiest way to avoid this extra hassle altogether.
Group sizes and prices:
It may be possible to arrange Nakasendo bike tours for bigger groups, but the sooner you book, the better. Your guides wish to avoid high impact in small villages, and stays in Japanese ryokans are often severely limited. Contact us prior to booking if your group has more than 8 people.
Min. age requirements:
If your group has riders under the age of 18, contact us prior to booking to make arrangements.
To get to GS Astuto base, the starting point of your tour, most people fly into Tokyo and one of its two airports, Narita International Airport (NRT) or Haneda Airport (HND). From there, you can take a train or a bus, it will take you 1.5-3 hours.
Covering all your bases with insurance is mandatory for this tour. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.
Deposits
Secure your spot with a 30% deposit upon booking! The remaining 70% of the trip price must be paid 90 days prior to departure at the latest. If booking within 90 days of departure, the full amount is required at the time of booking.
Cancellations
Booking fees are non-refundable after a 48-hour grace period. During checkout, however, you can choose one of 57hours’ flexibility options—Basic, Flexible, or Super Flexible. Depending on which one you choose, a different cancellation policy will apply to your booking.
Basic
Flexible
Super Flexible
