DAY 1 - Friday 29 May     

Arrive Tokyo  

This 12-day journey starts and finishes in Toyko before embarking on a fantastic cycling adventure through the scenic landscapes of the Nakasendo Trail and Mt Fuji.  

Our joining hotel is based at the airport – again, to make life easy for you. We see most of you arriving early. We will arrange the extra accommodation.   

Normal Ride Holidays traditions apply. Choice of rides daily. Yes – you will be challenged, but we also have to remember that it is a holiday. Team Mac will have their own guide and vehicle. 

This carefully planned itinerary combines incredible rides, stunning landscapes, and cultural immersion, making it a fantastic cycling experience in Japan. For this trip we’ll be joining forces with a local Japanese company.  

This afternoon, we’ll help you assemble the bikes. If you’ve hired a bike, then you’ll see it tomorrow. Tonight is our welcome dinner. Robbie will introduce you to the team and run through the first few nights together.  

Due to limited accommodation, this trip will be a smaller group size (max 20 cyclists and 5 non-riders). We suggest you book quickly to avoid disappointment. 

Bring on Japan... Tick tock. 

PS, a bit about the bikes. Road bikes with fat tyres are perfect. The hire bikes all come with 35mm tyres. Because the mileage isn’t massive you could also consider a gravel bike. There are also a range of e-bikes on offer.  

DAY 2 - Saturday 30 May  

Kyoto – via quite a fast train!!  

Toot Toot!! All aboard.  

Japan's bullet trains, known as Shinkansen, are world-renowned for their speed, safety, and efficiency. Introduced in 1964, the Shinkansen revolutionized rail travel with trains that now reach speeds of up to 320 km/h (199 mph). Connecting major cities such as Tokyo and Kyoto, these trains offer a smooth and punctual travel experience, often departing and arriving within seconds of their scheduled times. 

By the way, there are certain etiquette mistakes that tourists make when travelling in Japan. We don’t want to offend anyone, so we’ll make sure you are educated. One of those suggestions is punctuality. Don’t be late. It’s considered very rude. But, more importantly, if you are late for the Toot Toot then I doubt it will wait.     

This afternoon, Team Mac starts with a 20km run. Just joking!! But we do see you going for a good walk to shake off the cobwebs while the cyclists are riding their bikes. Tomorrow, you spend the whole day in Kyoto.  

Our hotel for the next couple of nights describes itself as a cultural exploration and serene escape. That’s perfect. After all, this is exactly why we’ve come to Japan.      

Cyclists – we anticipate that the majority of you will hire a bike, so today’s ride is only short. It’s purely to get you familiar with your new best friend. Tomorrow is out first real day in the saddle.  

On this particular trip, we’ve included all the dinners as we really want to make sure you are looked after.  

/ Accommodation: Kyoto             
/ Meals included: Breakfast, lunch and dinner  

DAY 3 - Sunday 31 May      

Exploring - Kyoto  

We explore Kyoto today. A city surrounded by mountains. Known for its rich cultural heritage, traditional wooden houses, classical Buddhist temples, Shinto shrines, and beautiful gardens. It was Japan’s capital for over a thousand years (from 794 to 1868) and remains one of the best preserved historic cities in the country.  

Team Mac - explores via foot with a local guide.  

Cyclists cover 70km, utilising the city's bike paths. Regularly voted one of the best cycling cities in Asia.  

Kyoto is home to more than 1,600 Buddhist temples and over 400 Shinto shrines, including famous sites like Kinkaku-ji (Golden Pavilion), Fushimi Inari Taisha (with its iconic thousands of red torii gates), and Kiyomizu-dera.  

Team Mac and the cyclists meet up for lunch in the Gion District which is known for its traditional tea houses and geisha culture.  

Tonight, we’ve arranged Kaiseki (a traditional multi-course meal), Yudofu (tofu hot pot), and Matcha (green tea). My feeling is that we may not lose any weight on this tour.   

/ Accommodation: Kyoto  
/ Meals included: Breakfast, lunch and dinner  

PS, here’s another hint. Don’t make this etiquette mistake. Don’t over tip. The Japanese pride themselves on fantastic customer service and have traditionally placed a much higher value on expressions of gratitude rather than cold, hard cash. 

DAY 4 - Monday 01 June  

We start the Nakasendo Trail

It is actually called ‘old-Nakasendo’, in Japanese 旧中山道(Kyu-Nakasendo). 

This is because the new Nakasendo is dedicated to cars and trucks and that’s not our target market. We will be riding the old-Nakasendo. This road is mostly paved and but there are sections of gravel (10%). 

The road is narrow - just one lane with many old houses and shops on both sides of the road. People, cars, bicycles, etc. all use this road. The speed limit is 40kph (some sections are only 30kph). The distance between each is less than 10km. This tour is not a race. 

The ride today is only 65km. Our target is Hikone. There will be an extension ride for those who want more mileage. There’s nothing stopping you getting to 100km. That’s on offer every day, but keep in mind that you won’t be travelling as fast as you would say in France. The other difference to Europe is that it’s pretty much flat. You’ll only climb 312m today. Struth, that’s almost all downhill.  

Team Mac – you visit Hikone Castle and then also have a good walk alongside Lake Biwa.  

Hikone Castle is one of only twelve castles in Japan with its original tenshu, and one of only five castles with buildings listed as National Treasures. 

Who is Teddy? It’s Teddy’s Bigger Burgers, of course, and that’s where both cyclists and non-riders meet for lunch. See you at Teddy’s.         

/ Accommodation: Traditional Japanese Ryokan 
/ Meals included: Breakfast, lunch and dinner    

PS, a traditional Japanese ryokan (旅館) is a type of Japanese inn that offers an authentic cultural experience, often centred around relaxation, hospitality, and traditional aesthetics.  

Key Features of a traditional ryokan: 

• Floors are covered with tatami mats (woven straw). 

• You’ll sleep on a futon (foldable mattress) laid out at night. 

• A multi-course traditional Japanese dinner, often featuring seasonal and local ingredients. Usually served in your room or in a private dining area. 

• Many ryokans are located near natural onsen and include communal or private baths. 

• Bathing etiquette is important (e.g., wash before entering the bath, no clothing/swimsuits). 

• A casual cotton kimono provided to wear during your stay. Many guests wear it to dinner and around the ryokan. 

• Deeply rooted in Japanese hospitality, staff often greet you with tea and are attentive but unobtrusive. 

DAY 5 - Tuesday 02 June      

Hikone to Inuyama 

72km. That’s all we need you to do today. East, sleep, drink and ride your bikes 72km. Struth, that sounds like a holiday.  

90% of what we ride is on the road. However, we will head off on some gravel from time to time to avoid the traffic. It’s very easy terrain. Not technical. Even Dingo could ride it.   

A quick note about the weather in June. It’s an ideal time for cycling in Japan. Expect daytime temperatures between 25 and 30°C, with cooler evenings around 15 to 19°C. Perfection.  

There will be many highlights today. One will be the Gifu Sekigahara Battlefield Memorial Museum. A modern, immersive facility dedicated to the pivotal 1600 Battle of Sekigahara, a decisive conflict that led to the establishment of the Tokugawa shogunate and the unification of Japan.  

Samegai-juku is #61 of 69 stations on the Nakasendō. During the Edo period, it served as a rest stop for travellers, feudal lords, and merchants journeying between Edo and Kyoto. It’s also known for its crystal-clear spring water, especially from the Jizō River (Jizōgawa) that flows through the town. The area is designated as a source of one of Japan's 100 Famous Waters. We recommend filling up your drink bottles here.  

Team Mac - also spend time at Inuyama Castle. Located on a hill overlooking the Kiso River. It is another one of the oldest of 12 castles to have retained its Tenshukaku intact. 

/ Accommodation: Traditional Japanese Ryokan 
/ Meals included: Breakfast, lunch and dinner  

DAY 6 - Wednesday 03 June    

Inuyama – Nakatsugawa 

There are 69 towns that make up the historic Nakasendō route. We’ve already travelled through 25. Our target today is #44 Nakatsugawa. Door to door is only 63km but is starting to get a bit lumpier with almost 700m of climbing.  

3 of the towns we ride through today are considered some of the prettiest. Unuma-juku #52, Mitake-juku #49 and Oi-juku #46. Keep in mind we are riding backwards.  

More importantly, where is lunch? Glad you asked. Cafe Maru in Nara is a beautifully restored Edo-era machiya townhouse. This café is renowned for its pancakes, both sweet and savoury. Seriously, who needs to go to Canada anyway? Eh.  

Speaking of food... a large chunk of your day is spent riding through rice fields. Seriously, who needs to go to Vietnam?  

Team Mac – let’s see how the fitness is but there is the chance for a 12km walk today. From Mitake to Hosokute and is a sure way of getting away from those pesky tourists (of which we are). It could be a good day to leave your comfort zone and visit an onsen. A natural hot spring, often found in hotels and public bathhouses. Japan has a deep bathing culture, and soaking in an onsen after a long ride is an incredible experience. Baths are typically gender-separated, and swimsuits are not worn. (Hence my comfort zone comment.)  

/ Accommodation: Traditional Japanese Ryokan 
/ Meals included: Breakfast, lunch and dinner  

PS, high above the rest of Japan at 2,702m above sea sits the caldera of Mount Norikura 乗鞍岳. A massive stratovolcano right in the middle of the spine of high peaks that separate Nagano and Gifu Prefectures. 

Other countries might boast higher summits, Norikura is home to the only 100% closed to cars road to the summit!! That’s right, no cars from 1,800m to the top. That’s 900m of gain on 13km of car free road to the top!! 

DAY 7 - Thursday 04 June   

Nakatsugawa to Kiso Fufushima 

Let’s start with the important people first – Team Mac. 5am we’d like you to go for a 1hr jog. Followed by yoga. If you pass both tests, then we’ll give you breakfast.   

In all seriousness, a highlight for you will be Kojitsu Coffee. A charming café nestled in the historic post town of Tsumago-juku, in Nagano Prefecture, Japan. It's an ideal stop for those seeking quality coffee and a relaxing atmosphere. Don’t feel too guilty knowing that the cyclists are slogging away while you are sipping on your lattes.  

Cyclists – hotel to hotel is only 56km with 700VM. But we’ve got a 40km out and back detour. Hmmm, some Upper Hutt maths here: 56km + 40km = hmmm, only 4km short of the ton. Believe me, we’ll find that 4km even if we make you go around the hotel car park a few times (as in 100). So, mark the century on your radar today.  

Highlight towns today include Nakatsugawa-juku (45th), Magome-juku (43rd), and Tsumago-juku (42nd). 

/ Accommodation: Traditional Japanese Ryokan 
/ Meals Included: Breakfast, lunch and dinner  
            

PS, a note on prefectures.  

Japan is divided into 47 prefectures. ·  Each prefecture has its own governor, legislature, and administrative bureaucracy. Prefectures handle local issues like education, infrastructure, and public safety. 

There are four types, though the differences are mostly historical or symbolic today: 

1. To (都) – Tokyo (metropolitan prefecture) 

2. Do (道) – Hokkaido (literally "circuit" but functions as a prefecture) 

3. Fu (府) – Osaka and Kyoto (urban prefectures) 

4. Ken (県) – The remaining 43 are standard prefectures 

DAY 8 - Friday 05 June   

Kiso Fufushima – Suwa  

Door to door is only 60km. There’s also a 16km bike path around the lake, so like on most days it would be easy to bulk up the mileage.

To get there there’s a little wee 1200m climb. Hmmm, isn’t that close to what we’d expect on Alpe d’Huez? Yes. And a bit!!  

Team Mac – by day 8 we’ll know exactly what makes you tick and will change the plan accordingly. Today is your sake Day. Hmmm, what’s a sake Day? Well, Lake Suwa is famous for its sake breweries, so we’ve arranged a tasting or 2. Cella Masumi, in particular, is known for its high quality sake. I’m sure everything will be fine.  Also, this region boasts over 500 hot spring sources. Notable options include Katakurakan, known for its large communal bath, and a free lakeside foot onsen near the Lake Suwa Geyser Center.  

Cyclists – I think we need to talk a bit more about today’s ride. You ride over the Torii Pass (鳥居峠, Torii-tōge). Elevation: ~1,362 meters. According to ChatGPT - Moderate to difficult climb, with winding roads and varying gradients (some sections exceed 8–10%). According to Silas, a false flat that you should be able to freewheel if you get up some speed.  

/ Accommodation: Traditional Japanese Ryokan 
/ Meals included: Breakfast, lunch and dinner  

Ps, we aren’t big on one-night stays. However, when riding the Nakasendo Trail you don’t really have a choice. We will try our best to have you at your hotel by early to mid-afternoon. You’ll have plenty of time for laundry, emails and basically chill before we have dinner.  

Day 9 - Saturday 06 June    

Lake Suwa to Mt Fuji 

Let’s talk about Team Mac first. Tomorrow, Mt Fuji will be busy. Busy with 8000 to 10000 cyclists. Today is the best day for you to visit Japan’s highest peak. The Mt Fuji Panoramic Ropeway, also known as the Mt Kachi Kachi Ropeway, offers a scenic cable car ride from the eastern shore of Lake Kawaguchiko up to an observation deck near the summit of Mount Tenjo. This short but memorable journey provides breathtaking views of Mt Fuji and the surrounding landscape. 

Le cyclists - it’s 90km door to door. At time of writing, we are sending our Japanese team on a recce mission to check out the best route. But it will include Wada. What’s Wada?   

The Wada Pass is considered one of the most difficult portions of the highway because of its steepness. Hmmm, define steep? Actually, let’s skip the description phase. Details like that aren’t helpful.   

This afternoon we register for tomorrow’s Fuji climb – Japan’s largest cycling event. It will be epic. There’s an expo village and 8000 other people to meet. That’s a lot of talking. Retail wise – this is your chance to buy some serious kit.  

Our team will also make sure your bikes are running smoothly before we turn in for a quiet night. Sleep well because tomorrow is go, go, go!!    

/ Accommodation: Fujikawaguchiko  
/ Meals included: Breakfast, lunch and dinner  

PS, trimming a bonsai tree in Japan is both a horticultural technique and an art form, deeply rooted in Japanese aesthetics and philosophy. Many bonsai nurseries offer hands-on trimming experiences for tourists. 

DAY 10 - Sunday 07 June  

The 21st Mt Fuji Hill Climb 

Over 8000 cyclists, ranging from beginners to seasoned riders. Let’s make that 8025 if you include 25 super-fast RH people in 2026.  

OK, a few disclosures. At time of writing, we don’t know the actual date. But we’ve taken a pretty good stab in the dark based on 2025.  

Regardless, if the event doesn’t run on 7 June 2026, we’ll be there. It will be just us. My guess is the media will be bigger if just 25 in pink and blue turn up.  

A bit about the event…  

It’s a 25km ascent along the Fuji Subaru Line, starting at Fuji Hokuroku Park and finishing at Mt Fuji’s 5th Station.  

Elevation Gain: Approximately 1,250 meters.  

Hmmm, there are some early numbers here.  

•   3:00 AM: Traffic control on Fuji Subaru Line begins 

•   4:00 AM: Parking lots open 

•   6:00 AM: Racers begin lining up 

•   6:15 AM: Opening and start ceremonies 

•   6:30 AM: First race start  

•  9am – Beer (just kidding, not kidding)  

Cyclists who complete the climb within specific time frames receive finisher rings (column spacers) in gold, silver, or bronze. For instance, a gold ring is awarded to those finishing in 1 hour and 5 minutes or less.  

Team Mac – we would love to involve you in the suffering. That will happen but we just aren’t sure how at this early stage.   

Tonight, we dine together. Let’s present the medals. It’s also the last chance we’ll be with some of the Japanese team. We raise a glass of sake to them. Thank you.     

/ Accommodation: Fujikawaguchiko
/ Meals Included: Breakfast, lunch and dinner  

DAY 11 - Monday 08 June  

DAY 12 - Tuesday 09 June  

Farewell  

Today, we say our goodbyes and head our separate ways. Whether you’re flying home or continuing your travels in Japan, we hope you leave with unforgettable memories, new friends, and a deep appreciation for the beauty of this incredible country. 

Closer to the time we’ll help with your departure transfer plans.  

Finally, on behalf of Ride Holidays – Thank You. We really appreciate your loyalty if you are a repeat offender. If this is your first RH experience, then we appreciate your trust. 

Safe travels home, 

/ Meals included: Breakfast