The Samurai Trail: Pilgrims & Picklers

The Samurai Trail: Pilgrims & Picklers

When: October 7th ~ 14th, 2019

Where: Nagano, Japan



Journey back in time to the ancient world of Japanese pilgrims and samurai by joining us for an unforgettable pickleball experience along the legendary Samurai Trail. On this tour, we will wander deep into the forests of the Sekida Mountain Range, trek along the 400 year old Nakasendo Road, and visit some of the most well-preserved, historical towns in the entire country. As an added bonus, we’ll be playing pickleball twice along our route! Accommodation will feature cozy cabins in the woods, Western style hotels, and traditional Japanese inns (Ryokans) with their own hot springs. If you’re not a fan of crowded cities or have visited Japan previously and want want to take a deeper dive into the culture, history, or rural lifestyle of this spectacular place, this is the trip for you!

Tour Package


  • $2250 PP Double Occupancy | $2750 PP Single Occupancy | $100 PP Non-Pickleball Player’s Discount


  • 7 nights of accommodation with complimentary breakfasts
  • All meals
  • All activities including tours, entrance & guide fees, pickleball clinics, transportation during the tour, etc.


  • Airfare to/from Narita Int’l Airport (NRT) or Tokyo Int’l Airport (HND) 
  • Alcoholic Beverages
  • Train ticket to Nagano City (starting point) or from Matsumoto City (end point)


Day 1 – Mon, October 7th | Meet in Nagano City

We will meet this evening at the Metropolitan Hotel Nagano inside Nagano Station, where we will have a welcome dinner. Further instructions will be provided on how to get to Nagano Station from various locations around Japan. For those playing in the Japan Open Pickleball Championships it is a 45 minute train ride from the tournament location to Nagano City.

Day 2 – Tue, October 8th | Begin Shinetsu Trail

After a buffet breakfast at the hotel, we transfer 45 minutes to Iiyama City to walk the first section of the Shinetsu Trail. We walk along the ridge top of a historic section of the Sekida Mountain Range today, getting deeper into the forest as the day goes on. Lunch is an bento box we buy before we start the day. After walking 12 km, the owners of the cabins where we will be staying pick us up. We go out for a hot spring onsen and dinner in the evening in a nearby town.

  • Hotel: Mori no Ie
  • Contact: +81 269-69-2888
  • Facilities: Cabins

Day 3 – Wed, October 9th | Finish Shinetsu Trail

Today is our second and final day on the Shinetsu Trail, where we walk around 12 km over fairly rough up and down terrain. Lunch is a bento box that a local lady prepares for us. Mori no Ie picks us up again and we return in the afternoon for some time to relax in the cabins or go for a walk in the beautiful farm country. We go out to dinner in a local ski village as well as another hot spring onsen.

  • Hotel: Mori no Ie
  • Contact: +81 269-69-2888
  • Facilities: Cabins

Day 4 – Thu, October 10th | Iiyama ~ Kiso Fukushima, Pickleball in Kiso Fukushima

This day we will travel 2 hours from Iiyama City to Kiso Fukushima. Don’t worry, this is not the same Fukushima as the nuclear accident! We have a soba lunch at a famous buckwheat noodle restaurant and play pickleball in the afternoon. Dinner is a kaiseki style Japanese banquet at the Japanese inn (ryokan) where there is also a hot spring (onsen) to soak in in the evenings.

  • Hotel: Onyado Tsutaya
  • Contact: +81 264-22-2010
  • Facilities: Japanese-Style Inn*

Day 5 – Fri, October 11th | Walking the Nakasendo

This morning we take a train 45 minutes to Nagiso where we will start walking on the historic Nakasendo Trail. An hour walk brings us into Tsumago, one of the most well-preserved Japanese post towns in the whole country. We have a snack and a rest here, before continuing another 7 km to Magome, where we have a late lunch. A short bus and train ride take us back to Kiso Fukushima. On the walk home, we go to a sake brewery for a tasting. Dinner is sumo wrestler style, a hot pot called Chankonabe.

  • Hotel: Onyado Tsutaya
  • Contact: +81 264-22-2010
  • Facilities: Japanese-Style Inn*

Day 6 – Sat, October 12th | Kaida Kogen, Pickleball in Kiso Fukushima

Today we take a taxi to Kaida Kogen, where we walk over the beautiful Jizo Pass. A lovely couple hosts us for lunch, before we continue walking through blueberry fields and a dairy farm. On a clear day, we can catch spectacular views of the nearby Mt. Ontake. We take a bus back to Kiso Fukushima, and join local pickleball players for a game in the evening. Dinner is in a local izakaya style restaurant with some of the pickleball players from the club.

  • Hotel: Onyado Tsutaya
  • Contact: +81 264-22-2010
  • Facilities: Japanese-Style Inn*

Day 7 – Sun, October 13th | Kiso Fukushima ~ Matsumoto

Today we transfer 20 minutes to Yabuhara and walk over the Torii Pass around 9 km. We descend into the town of Naraijuku, the last of the post towns we will be visiting on the Nakasendo Trail. We have lunch at another famous soba restaurant before taking the train 45 minutes to Matsumoto, where we see Matsumoto Castle. Dinner is at a local yakitori restaurant.

  • Hotel: Hotel Kagetsu
  • Contact: +81 264-22-2010
  • Facilities: Western-style Accommodation

Day 8 – Sun, October 14th | Departure

Today you will transfer from Matsumoto to your onward destination. Tokyo’s Shinjuku Station is 2.5 hours away, from where there is a direct train to Narita or Haneda International Airport.
Please make sure your flight does not depart too early this day as it takes over 3 hours to return
to Narita or Haneda.

*Note: Staying at a Japanese-style inn means sleeping on a comfortable futon mattress laid on top of a tatami mat floor. All the rooms will have showers but this inn also has hot springs if you want to try soaking in them.

Cancellation Policy

  • 60 ~ 31 Days Prior to Arrival: 20% of the Total Costs
  • 30 ~ 4 Days Prior to Arrival: 50% of the Total Costs
  • 72 Hours or Less Prior to Arrival: 100% of the Total Costs

Please contact us at if you have any additional questions regarding our cancellation policy.

Travel Insurance

We strongly encourage all travelers to invest in travel insurance to both minimize your financial risks of traveling and provide you with peace of mind to fully enjoy the your trip. Travel insurance can provide many helpful resources including refunds or assistance for any of the following situations that may arise before or during a trip:

  • You need to cancel your participation on the tour
  • You need to cancel or change a flight
  • Lost baggage during the trip
  • Stolen items during the trip
  • Medical costs during the trip

We suggest you talk to your insurance provider to ask about the travel insurance plans available to you. You can also compare policies online. Here are two well-known travel insurance providers to consider:

Please contact us at connect@pickleballtrips.comif you have any additional questions regarding travel insurance.

Past Reviews

“This was our first trip to Japan, and our first (but not last) Pickleball Trip. It was one of our best vacations ever! Daniel is the perfect guide and tour leader- super nice, friendly, fun, and knowledgeable. He and our other instructor, Randy, are great teachers. In addition to arranging for us to play with enthusiastic and friendly Japanese players and teams, they gave us invaluable help with our individual games to improve our skills. And they were so much fun to travel with. Traveling by train was a great way to see Japan, and Daniel made it so easy for us; he handled all the arrangements smoothly-from navigating the train system, to taking us to interesting historical sites, to our food & hotels. The accommodations were more luxurious than we expected. The food was varied, copious & oishi (delicious). We also enjoyed getting to know and traveling with the other group members, who were adventurous and fun-loving. In conclusion, this was a uniformly wonderful travel experienceWe are already looking forward to our next vacation with Pickleball Trips next year.”

Laurie V – 2018 Autumn in Japan Participant

“. . . a marvelous adventure into Japanese culture through a variety of experiences—sumptuous Japanese cuisine, ancient temples, bustling trains and subways, traditional Japanese baths, even a romp in a Japanese dollar store! But the best part was making new Japanese pickle ball friends along the way. Daniel is a knowledgeable guide and a skilled pickle ball instructor.  I came home with a full heart and some great feedback to improve my game.  I highly recommend this trip to anyone who likes to get out of the tourist bubble and experience another culture in a more meaningful way.” 

Jeanne H – 2018 Autumn in Japan Participant

“My husband and I just got back from Pickleball Trips’ Autumn in Japan trip with Daniel Moore and guest pro Randy Coleman. It was a first-class experience from start to end including the food, accommodations, and activities. Daniel shared with us his favorite parts of Japan including gorgeous scenery, wildlife, and world heritage sites. We had clinics with Daniel & Randy and got to play Pickleball with Japanese players in three different cities. I highly recommend this trip to anyone who enjoys traveling and Pickleball. My husband wants all of our future vacations to be Pickleball Trips! Thank you for the trip of a lifetime!!!”

Farrah O – 2018 Autumn in Japan Participant

“The 2018 Japan Pickleball Trip was fantastic! I would do it again. Let me explain some of the
highlights-and there a lot. First, the hotels and restaurants were great. Each day exceeded the
prior day and my expectations. Second, the trip mixed in small villages with large cities. Third, Daniel Moore is the consummate pro: as a guide; as an expert bus driver; a train navigator; and believe it or not, at Karaoke. The trip took us to World Heritage sites, the Snow Monkey Park, and a castle here and there. Fourth, the bullet trains (with the JR Pass) were easy to navigate (with Daniel’s help), comfortable, and fast. Great way to get around Japan. Fifth, the food was awesome; there were variations at every stop. Daniel took us to out of the way places to eat, and then eat again, and eat again. Sixth, we received Pickleball instruction throughout the trip and played with and against Japanese PB teams and players. This trip is a great way to see, experience and immerse yourself in Japanese culture and do it playing Pickleball. I rate this trip a 10 out of 10.”

Howard V – 2018 Autumn in Japan Participant