DAY 1 - Friday 28 May     

Arrive Tokyo  

We recognise the majority will have been in Japan for a couple of days. You will be well recovered from the long flight and be ready to go.  Welcome to those arriving today.

About half of you have your own bikes. This afternoon we’ll help you assemble them. Those hiring bikes will see them for the first time tomorrow when we arrive in Kyoto.  

Let’s get together at 5pm. Tim and Naoko will introduce the team and run through the plan for the next few days. Tonight (7pm) is our welcome dinner at the hotel. 

Dinner – what can we expect over the next 12 days or so? Well, I doubt you’ll lose any weight. Please keep in mind that we are in Japan to experience Japan.   Traditional Japanese cuisine, known as washoku, emphasizes seasonality, balance, and respect for natural flavours, using fresh ingredients prepared with minimal intervention. Meals often centre around rice, accompanied by miso soup and a variety of side dishes featuring fish, vegetables, tofu, and seaweed, with cooking methods such as grilling, simmering, steaming, and raw preparation (as in sashimi).

Sake is that charming Japanese beverage that politely bows on the way in and then, an hour later, starts singing karaoke through you. It looks innocent in its little ceramic cup, tastes smooth and refined, and quietly convinces you that ordering “just one more” is a culturally educational decision.

When clinking glasses in Japan, it’s polite to slightly lower your glass if the other person is older or of higher status—a subtle nod to respect.

DAY 2 - Saturday 29 May  

Kyoto – via quite a fast train!!  

Toot Toot!! All aboard.  

Japan’s bullet trains, known as Shinkansen, are world-famous for their speed, safety, and punctuality, forming the backbone of long-distance travel across the country. Reaching speeds of up to 320 km/h, the Shinkansen connects major cities (like Tokyo and Kyoto for example) with remarkable efficiency, comfort, and reliability, often arriving within seconds of schedule.

Some stats….

Distance: Approximately 513 km. Travel time: 2 hours 15 minutes. Struth…. That’s quicker than the train from Wellington to Upper Hutt and back again (50km rtn). Hold on tight!!

Upon arrival in Kyoto, we check-in to our hotel. Noku Kyoto is a stylish boutique hotel in the heart of Kyoto, Japan, blending modern comfort with the city’s rich cultural heritage. Located a short walk from Marutamachi subway station and within easy reach of the Kyoto Imperial Palace and historic neighbourhoods, it provides an excellent base for exploring Kyoto’s temples, gardens, and traditional streets.    

This afternoon, Team Mac starts with a 20km run. Just joking!! But we do see you going for a good walk on most days. In all seriousness - Naoko has arranged a tea ceremony and Japanese sweet making session starting at 3.30pm. 

Cyclists - today’s ride is only short. It’s purely to make sure you and your bikes are working as they should.  

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

/ Accommodation: Noku Kyoto            
/ Meals included: Breakfast, Lunch (Bento on the Toot Toot) and Dinner 

DAY 3 - Sunday 30 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. With around 1.46 million residents it is alsoone of Japan’s larger cities.  

Team Mac - explores the Gion district via foot with a local guide (2 hours). Kyoto is home to more than 1,600 Buddhist temples and over 400 Shinto shrines. This afternoon there’s the option of visiting Kinkaku-ji (Golden Pavilion). This iconic Zen Buddhist temple is famous for its stunning gold-leaf exterior, serene reflecting pond, and beautifully landscaped gardens, offering a perfect blend of history, art, and nature. It attracts millions of visitors each year and is emblematic of Kyoto’s rich cultural heritage.

Cyclists – the plan is to cover 50km, utilising the city's bike paths. Regularly voted one of the best cycling cities in Asia. With relatively flat terrain in the city centre and well-marked lanes along rivers, canals, and historic streets, cycling allows visitors to access temples, shrines, and traditional neighbourhoods at their own pace. Our route includes the Kamo River path, which stretches through the heart of the city, and the philosopher’s path, lined with cherry trees and small temples. 

Tonight, we’ve booked a Shabushabu restaurant called Chiriri near Noku (5min walk). Shabushabu is a famous Japanese hotpot dish featuring thin slices of high quality pork or beef. We have requested fish (sea bream) for those who don’t eat meat. There are some tofu, vegetables and udon noodles as well. Struth, it’s just as well that lycra expands.    

/ Accommodation: Noku Kyoto
/ Meals included: Breakfast, Lunch and Dinner  

DAY 4 - Monday 31 May 

We start the Nakasendo Trail (Kyoto to Gifu #53)  

It’s 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 a mixture of the old-Nakasendo as well as jumping on to quieter roads where we have the opportunity.

Today should be looked at as a transition day. From the city to the Gifu Plains. It won’t be your #1 day on the bike while in Japan. That will come later in the week. Today’s route threads suburban backstreets and canal roads east of the city before transitioning into classic inland Honshu terrain: folded hills, river valleys, and long connective roads that historically bound Kyoto to Edo.   

There are a few ride options to choose from. We suggest that the cappo and single shot latte cyclists start at the 30km mark (via the train) on Lake Biwa (Japan’s largest freshwater lake). It means you get to avoid all the traffic congestion (about 2 hours) when leaving Kyoto. Your bikes will be there to meet you after you arrive. It’s then just over 100km to the hotel but you can pull the plug at any stage. Even 70km for the first day is pretty solid.      

The espresso option goes hotel to hotel. The first 80km is pretty much flat. The last 60km is a wee bit lumpier. Our target is Gifu. The longest ride on offer is 142km but we only expect a small handful of you to do this.

Team Mac – you visit Hikone Castle. One of only twelve castles in Japan with its original tenshu, and one of only five castles with buildings listed as National Treasures. The castle gardens, known as Genkyūen, are a beautifully preserved Edo-period strolling garden located at the foot of the Castle. Designed in 1677, the garden features a large central pond, elegant bridges, manicured pine trees, and a traditional teahouse, all carefully arranged to frame stunning views of the castle. Naoko will also plan a good walk every day. There’s a good chance today’s stroll will be alongside Lake Biwa. The plan this afternoon is flexible. Let’s see where the cyclists are and try to arrive in Gifu at the same time as them.      

/ Accommodation: Miyako Hotel Gifu Nagaragawa 
/ Meals included: Breakfast, Lunch and Dinner    

DAY 5 - Tuesday 01 June      

Gifu (#53) to Nagiso (#42)  

In summary, we move decisively east through the historical heart of Mino Province, trading the openness of the Gifu basin for increasingly folded terrain as the route follows the Kiso River system toward Nakatsugawa. The riding is defined less by traffic or spectacle and more by structural continuity: post town spacing, river-aligned gradients, and roads that still mirror Edo-period movement logic. By the end of the day, the landscape tightens, gradients assert themselves, and the sense of approaching the Kiso mountains becomes unmistakable. Kiso-ji is a summit finish, a clear threshold—beyond here, the route commits fully to mountain travel.

Cyclists - the good news is that the first 50km is pretty much flat. Pretty much!! We see the cappo and latte riders starting at the hotel and riding as far as you can. Even if you make it to Ena and stop there. That would make it 86km and would also give you a wee taste of the hills that are on the horizon for the next few days. Espressos - tonight’s hotel is exactly 122km away. Hmmm, there’s quite a bit of climbing though with about 2000VM. Yes – there will be plenty of support along the way.

Team Mac – what does your day look like? 6am – our standard 15km run. Actually, let’s not do that, however Naoko has planned an early walk at (#43) Magome juku which is one of the more beautiful Edo-period towns and well worth the wander. The jewel in today’s Team Mac crown is the Museum Meiji-Mura. A unique open-air architectural museum and historic theme park in Inuyama, Aichi Prefecture, Japan, near Nagoya. It was established in 1965 to preserve and showcase authentic buildings and cultural architecture from the Meiji period (1868–1912) — a time when Japan rapidly modernised by incorporating Western influences into its society and architecture.  

Our hotel for this evening - TAOYA Kisoji is a well-known ryokan-style hotel and hot spring (onsen) resort. This evening you can relax in hot spring baths, including outdoor open-air baths with panoramic mountain scenery, as well as enjoy saunas and wellness services (massage, etc). 

/ Accommodation: TAOYA Kisoji
/ Meals included: Breakfast, Lunch and Dinner  

DAY 6 - Wednesday 02 June    

Nagiso (#42) – Lake Suwa (#28)  

Today we start at #42 and finish at #28. Narrow valleys, increasing gradients, and the road structure becomes unmistakably pre-modern in logic: river-following where possible, ridge crossings where unavoidable. Historic post towns appear not as destinations but as functional waypoints, reinforcing the sense of continuous movement rather than staged sightseeing. The day resolves dramatically with a long descent into the Suwa basin, where open water, wider skies, and settlement density signal arrival into Shinano’s interior heartland. 

Hotel to hotel is 114km and hmmm…. 1770m of climbing including the 500VM Torii Pass which stands at 1200m above sea level. It will become very obvious who has and who hasn’t followed the Silas Cullen training program. Again – we’ll have a plan for those not wanting to ride the whole way.

#40 is a town by the name of Kiso-Fukushima and we think that will be our lunch destination. It’s known for being Bambi friendly. Yes – Japanese deer. We propose that we invite one for lunch. 

Venison burger for lunch.  

Our destination is Lake Suwa. Surrounded by the mountains of the Suwa region, and has long been a natural and cultural focal point of the Nakasendō. For centuries, travellers passing through Suwa-juku paused here to admire the open water after days of mountain roads, while locals depended on the lake for fishing, transport, and seasonal rituals. Lake Suwa is especially famous for the omiwatari, a rare winter phenomenon where ice ridges form across the frozen surface and were traditionally believed to mark the path of the gods. 

Team Mac – your day sounds like a lot of fun. You start with a walk along the Kiso River. Starting at Tsumago-juku and walking along the Nakasendo to Midono-juku, which is about 5km. It’s then on to the glass art museum and finally – you learn how to make Lacquerware chopsticks. 

Everyone - this is optional. There are 5 Sake breweries all on the same street near the hotel (15min walk). We can arrange to visit all 5 (90mins) of them if you like? The cost is 3,000yen per person. Naoko will gauge interest in making it happen if you are keen.   

/ Accommodation: Kamisuwa Onsen Hamano Yu
/ Meals included: Breakfast, Lunch and Dinner 

DAY 7 - Thursday 03 June   

Suwa (28) to Yatsugatake  

Today sees us leave the contained world of the Suwa basin and trend south, skirting the western flanks of the Yatsugatake range before dropping decisively into the Kai Basin. The riding alternates between elevated farmland and forested uplands. Historically, this corridor functioned as a connective interior route rather than a formal post-town chain, and that character remains evident: fewer towns, longer gaps, and roads built for continuity rather than ceremony. By the time the ride settles into Kōfu, you will have fully transitioned from interior mountain corridors to basin-to-volcano geography. 

There are 2 ride options. One is easier and the other is ahhh, actually quite challenging. Cappo // single shot latte option. Door to door is only 55km but still involves over 1000m of climbing. Let’s call it easy, but not easy. ** Keep in mind that hotel check-in is generally 3pm so there’s no point in arriving too early. 

Double shot latte // espresso is slightly longer. 80km (hotel to hotel) but you have 2000VM as you feature the Fujimi Highlands Ascent. Cat 2 climb, with 700m of climbing. The good news is that the last 45km is pretty much all downhill. You see – we always offer good news. Lunch will probably be in Hara as that’s about halfway.

Team Mac – by day 7 we’ll know how much walking you like and will adjust the plan accordingly. First stop (after coffee of course) is a visit to the Suwa Taisha shrine (where you will receive a Goshuin). The most significant Shinto Shrine in Kanto.There are 4 major shrines in the Suwa area, all connected historically.

What is a Goshuin? It is a special stamp or seal that is a unique form of Japanese religion and culture, with centuries of tradition behind it. 

Team Mac - you then drive to the Kawamata river valley. There are numerous trails alongside the river. The plan is also to visit the Doryu waterfall. You also visit the Yatsugatake Kogen Bridge known locally as the “Yellow Bridge” distinguished from the nearby Higashizawa Bridge (“Red Bridge”) due to its bright yellow colour. Anyway – Yatsugatake is 500m in length and 100m above the valley floor. On a clear day you can see the Yatsugatake Mountains, The Southern Alps to the southwest and Mt Fuji to the south. 

Tonight’s hotel is probably your most western like hotel on the trip. Nestled at the foothills of Mt. Yatsugatake. Make sure you spend some time on the rooftop observation deck (“Yatsugatake SoRa Deck”) for star gazing and mountain views.   

/ Accommodation: Grand Mercure Yatsugatake  
/ Meals Included: Breakfast, Lunch and Dinner       

DAY 8 - Friday 04 June   

The World’s Oldest Hotel!! 

According to the Guinness World Records - Nishiyama Onsen Keiunkan was founded in 705 AD — making it over 1,300 years old. Amazingly, it is still owned and run by the same founding family. Currently the 52nd generation. The rooms are tatami-matted with futon bedding. It’s also registered as one of Japan’s historic hot spring inns. 

Let’s start with Team Mac. It’s important while in Japan that you learn how to trim a Bonsai. A horticultural technique and an art form, deeply rooted in Japanese aesthetics and philosophy. Your class is 2 hours long. Your tree of choice is an olive tree. How do I know that? Because we’ve had to buy them for you to trim. You are welcome to take it home afterwards. (Customs depending of course.)  You then visit the Minobusan Kuonji Temple which is one of Japan’s most important and historic Buddhist temple complexes — especially for followers of Nichiren Buddhism, and a profound pilgrimage site in Yamanashi Prefecture.

Cyclists - pretty much dead pan flat from door to door. Except for the Hayakawa Valley Climb. At the 40km mark you have the Cat 2 14km, 1100m climb. (Pretty much the same stats as d’Huez. Gulp!!) Nothing for climbers in the family but the sprinters may be looking at today with some trepidation. Yes – there will be a plan B and C. 

Today’s ride follows the Hayakawa River corridor into one of Yamanashi’s most sparsely populated regions, where road access historically existed primarily for resource movement rather than transit.

Hotel to hotel is exactly 76km. That doesn’t sound too bad!! More good news. The last 20km is all downhill. Except for a wee wee bit of uphill. But mainly downhill. 

/ Accommodation: Nishiyama Onsen Keiunkan
/ Meals included: Breakfast, Lunch and Dinner

PS, before I’m asked. Tonight’s hotel has had various renovations including a major upgrade in 2025. You’ll be very comfortable.  

Day 9 - Saturday 05 June    

Mt Fuji – Here we come!!

Le cyclists - it’s 90km door to door. 

But – that’s over quite a large mountain range. Recognising that a few of you will want to be resting in prep for tomorrow we’ve come up with 2 options. 

1. Let’s call this the – I will ride, ride, ride option. Hotel to hotel. 90km. A spot over 2000m of climbing. Legends. But, yes, you will be publicly drug tested if you take this option.

2. Beam me up Scotty. This involves a lift to the top of the hill. (We’ll have to do this in separate shuttles if you all decide to do this.) You then have 65km of descending and flat (ish) terrain to the hotel. Personally – this would be my pick. Rolling the legs over while leaving something in the tank for tomorrow. 

So, your choices…. Ride, Ride Ride or Beam me up Scotty.  

Team Mac - Naoko has booked a Hoto Noodle making experience near Kawaguchiko. Hoto is a regional popular dish originated from Yamashi prefecture. You all wanted cooking experiences so here you go…. Enjoy your lunch. 

Our hotel for the next couple of nights is a large resort hotel and spa offering Mt Fuji views from many rooms. (Fingers crossed.) For those thrill seekers amongst us – it’s a 5min walk to Fuji-Q Highland. A major amusement park. Famous for its record-breaking roller coasters. Hmmm, no thanks but the choice is yours. 

/ Accommodation: Highland Resort Hotel & Spa
/ Meals included: Breakfast, Lunch and Dinner    

DAY 10 - Sunday 06 June  

The 23rd Mt Fuji Hill Climb 

9000 cyclists, ranging from beginners to seasoned riders and professionals. Let’s make that 9025 if you include 25 super-fast RH people.

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.

The men's record is 1hr 6mins. Women – 1hr 16mins. The oldest cyclist to finish is 83 years of age. 8% of entrants are women. 5% are overseas cyclists made up mainly from Taiwan, China and HKG. 98.8% of those who start – finish. (No pressure!!) 

Plan B ride for the e-bikers – Tim has an alternative route planned for you. He actually prefers it to what the event is doing. Your day will be – riding and supporting.     

Team Mac – Naoko is planning on getting you to the cable car as soon as it opens. To avoid the queues. We would then love you to be involved in the event somehow but not sitting on the side of the mountain for 5 hours.

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: Highland Resort Hotel & Spa
/ Meals Included: Breakfast, Lunch and Dinner  

DAY 11 - Monday 07 June  

DAY 12 - Tuesday 08 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 departure transfer plans. 

Finally, on behalf of Ride Holidays – Thank You.

We really appreciate your loyalty if you have travelled with us in the past. If this is your first RH experience, then we appreciate your trust.

Safe travels home, 

/ Meals included: Breakfast