Included:

• • 8-day self-guided Nakasendo bike tour (7 days of cycling, plus a short orientation ride on Day 1)
  • Accommodation for 8 nights, double occupancy (traditional Japanese ryokan for most nights, with a ryokan or 4-star hotel in Hikone, and a hotel in Kyoto)
  • Pre-mapped daily routes with GPS tracks (your guides help you set up your Garmin or other GPS)
  • High-end premium rental bike (or e-bike)
  • SAG van & driver / mechanic
  • Luggage transfer between each stop
  • Breakfast and dinner daily
  • Ride snacks & water (fruit & nuts, electrolytes)
  • Entry tickets to castles, museums, and shrines, as listed in the itinerary
  • On-demand support

Add-ons (pricing shown at checkout):

• • Single occupancy room
  • Guide — possible to arrange at an additional cost, reach out if interested

Not included:

• • Flights to Japan
  • Domestic transport (train tickets, buses, airplanes)
  • Support & gear on demand (while there is van support, the group is not followed and there is no support with incidentals)
  • Alcoholic beverages
  • Lunches
  • Any additional stops or visits that aren’t explicitly mention in the “Included” section
  • Helmet
  • Anything not mentioned in the “Included” section above
  • Insurance — mandatory, available to add at checkout

In order to join this Nakasendo self-guided cycling tour, great fitness is required as well as basic riding experience. The most you’ll cycle within a day is up to 72 km (45 mi), with up to 1,204 m (3,950 ft) of elevation gain.

While e-assist bikes are available and significantly reduce the effort required on the climbs, they don’t replace the need for basic riding skills and day-to-day endurance. Since you’ll be riding at your own pace with no escort, following GPS tracks and route notes is part of the experience—your guides map every turn in advance so you always know where you’re headed. We’ve welcomed riders of all ages and fitness levels on this route, though it’s a real challenge, especially over Wada Pass and the Kiso Valley’s thirteen passes.

Want to see what else is there in the area? Discover more Japan cycling tours here!

The Nakasendo is a historic mountain road that connected Edo (modern-day Tokyo) and Kyoto during the Edo period (1603–1867), serving samurai, merchants, and pilgrims as an inland alternative to the coastal Tokaido route.

The full road ran about 534 km (332 mi) and was marked by 69 post towns, spaced roughly every 10 km (6 mi), where travelers could rest, eat, and find lodging. Much of the original route has since been absorbed into modern roads and cities, but stretches through the Kiso Valley in Nagano and Gifu Prefectures remain remarkably intact, with wooden post towns, stone-paved sections, and mountain passes still walkable and rideable today.

Here’s what you’ll need:

• • Comfortable riding or athletic clothing, preferably moisture wicking or synthetic material
  • Leisure clothing for the afternoons/evenings
  • Sneakers or sport shoes
  • Breathable outside layer or jacket
  • GPS — your guides can assist setting up your Garmin or other GPS
  • Helmets
  • Sunglasses
  • Plenty of water, water bottle or hydration bladder
  • Daypack with snacks
  • Biking gloves are optional but recommended
  • Toiletries (sunscreen, hand sanitizer, bug spray, toilet paper, etc.)

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).

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Self-guided tours are perfect for those who enjoy exploring on their own terms—at their own pace, and with the company they choose. By joining this self-guided Nakasendo Trail, we take care of:

• • Accommodation for 7 nights, double occupancy (traditional Japanese ryokan for most nights, with a ryokan or 4-star hotel in Hikone, and a hotel in Kyoto)
  • Pre-mapped daily routes with GPS tracks (your guides help you set up your Garmin or other GPS)
  • High-end premium rental bike (or e-bike)
  • SAG van & driver / mechanic
  • Luggage transfer between each stop
  • Breakfast and dinner daily
  • Ride snacks & water (fruit & nuts, electrolytes)
  • Entry tickets to castles, museums, and shrines, as listed in the itinerary
  • On-demand support

Rather than joining a guided group, you’ll navigate the tour yourself, using resources provided by the tour operator. For a hassle-free journey with everything arranged for you in advance, there’s no better option!

As a self-guided tour is built around your preferred travel dates, your guide will take care of arranging accommodations and details after you book. Note that exact accommodations and dates might shift slightly, so don’t make any travel arrangements until the details of your adventure are confirmed.

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 takes a minimum of 4 people for this tour to operate. The maximum group size is set at 8 participants.

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 you are older than 18, you’re good to go.
  • Children as young as 10 are able to go on trips with a legal guardian. That said, if you have a young rider strong enough to handle sustained climbs (either riding or walking their bike) of hundreds of feet, and rough terrain, then they may be able to participate on a case-by-case basis.

If your group has riders under the age of 18, contact us prior to booking to make arrangements.

The price for this self-guided Nakasendo Trail is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.

The starting point of your self-guided tour is the guide’s base in Matsuida, Gunma Prefecture. To get there, 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 bus, which takes about 1.5–3 hours.

You’ll meet your tour operator on Day 1 in Matsuida for orientation and bike fitting.

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.