DAY 1 - Wednesday October 14

Arrive in Onomichi

Welcome to Onomichi! This fascinating port town is the gateway to the Shimanami Kaido Islands and Bridges Cycle Route. Easily accessed by bullet train or local train, our beautiful cycling-themed hotel is located on the wharf, just a 5-minute walk from the station.

After brief introductions, we’ll help set up your bikes and ensure everything is running smoothly. Let’s pop out for a short shake-down ride. Will and Robbie will introduce the team and answer any questions.

My guess is that you won’t lose any weight on this trip. Japanese cuisine offers a great variety of fresh seafood, meats, and vegetarian dishes. Many of our hotels provide buffet-style breakfasts and dinners, allowing you to try a range of local flavours. Yes, you will eat well.

Let’s raise a glass (Sake) to the adventure ahead.

PS, we realise you won’t be able to book flights until November 2025. Prior to you confirming flights, we will give some advice on the best way to get to Onomichi. At this early stage, Robbie will be in Hiroshima and will organise travel as a group. To be confirmed.

PPS, a quick note about the weather. Mid-to-late October is an ideal time for cycling in Japan. Expect daytime temperatures between 20–25°C, with cooler evenings around 15°C. Autumn colours will be starting to show, especially in the mountains, making for some stunning rides.

DAY 2 - Thursday October 15

Onomichi to Ikuchi Island – Shimanami Kaido Cycling

After breakfast, we’ll jump onto our bikes and ride hotel to hotel. It’s not a massive ride at only 55km (400VM) but it’s a great way of starting our cycling holiday. A very short ferry ride gets us to the start of the Shimanami Kaido. Today is a stunning ride on one of the best cycling routes in the world! We’ll explore the islands, jumping off the beaten path to visit a local shrine and soak in the views.

Our destination for the night is Ikuchi Island, famous for its citrus groves and cycling-friendly roads. After arriving, you’ll have time to unwind in the hotel’s beautiful spa before we enjoy a well-earned dinner featuring fresh local seafood and produce.

Team Macchiato: While the cyclists are out conquering the Shimanami Kaido, Team Mac enjoy a morning temple walk through the fascinating old streets and alleyways of Onomichi and visit the stunning Senko-ji Temple observatory for fantastic views of the town and the Inland Sea. After lunch in Onomichi, hop into the van and head to the islands, stopping at Shirataki-yama, a mountain viewpoint offering 360-degree views of the islands and bridges. From there you’ll make your way to Setoda on Ikuchi Island, where you’ll have time to relax at the hotel’s spa or explore the old shopping arcade of this charming fishing village.

/ Accommodation: Ikuchi Island Hotel
/ Meals included: Breakfast, Lunch & Dinner

DAY 3 - Friday October 16

Ikuchi Island to Saijo – Shimanami Kaido Cycling

Today, we continue the Shimanami Kaido cycling route. A slight increase on yesterday’s mileage with 75km and 600VM being the main ride. On that note, the team will always have a plan for those wanting extra kms.

Japan’s roads are smooth, well-maintained, and often have little traffic—perfect for cycling.

Climbs are well-graded, downhills are fun and flowing, and drivers are very courteous.

Another breath-taking ride takes us across beautifully engineered bridges, each offering spectacular views of the Seto Inland Sea and its scattered islands. We’ll also visit Oyamazumi Shrine, one of the region’s most ancient and significant shrines, steeped in samurai history.

We’ll finish the ride cycling over the 4km long Kurushima suspension bridge and onto Shikoku Island. A short transfer to our accommodation, which features a rooftop hot spring—the perfect way to relax and recover while taking in mountain and sea views.

Team Macchiato: While the cyclists are out riding the Shimanami Kaido, Team Mac will have a few optional activities to choose from. They can join a guided citrus farm tour on Ikuchi Island, where they’ll learn about the island’s famous citrus groves and sample some fresh produce. Alternatively, they can take a short cruise near the Tatara Bridge for a different perspective of the Inland Sea. Afterward, they’ll continue their journey toward Shikoku, stopping at some fascinating spots along the way.

/ Accommodation: Saijo Hotel
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

DAY 4 - Saturday October 17

Saijo to Uchiko – UFO Line & Mt. Ishizuchi

Today’s ride is a big one, but it’s also one of the most rewarding. 115km and 1500m of climbing. Yes, we’ll have a latte and cappuccino plan for those not wanting to ride the whole distance. Today we tackle the UFO Line, a stunning route that winds its way up Mt. Ishizuchi, the highest peak in western Japan. The panoramic views stretch across rugged mountain ranges to the Pacific coast—it’s worth every pedal stroke.

After the epic climb and exhilarating descent, we’ll stop for lunch in Omogo Gorge, known for its crystal-clear waters and dramatic rock formations. From there, we’ll ride through emerald-green river valleys, passing small villages and pristine countryside as we make our way to Uchiko. A hidden gem, famous for its well-preserved historical district and charming old merchant houses. It’s like stepping back in time to a quieter, more traditional Japan.

Team Macchiato: Team Mac head to Matsuyama City, Shikoku’s largest city. Here, they’ll visit Matsuyama Castle (optional entry) and take in the city’s rich history and culture. They’ll also stop at a local dyeing shop, where they can try their hand at indigo dyeing—a fun and unique experience. After lunch in the city, they’ll make their way to Uchiko to reunite with the cyclists and enjoy a wonderful group dinner.

/ Accommodation: Traditional houses in Uchiko
/ Meals included: Breakfast, Lunch & Dinner

DAY 5 - Sunday October 18

Uchiko – Rest Day

Shall we call it an active rest day. There’s still a 30km coffee ride on offer.

Today is all about slowing down and soaking in the charm of Uchiko. We’re staying in traditional houses within the historic district, beautifully refurbished into modern Japanese style accommodation. Think sliding paper doors, tatami mats, and a serene atmosphere— it’s the perfect place to feel at home away from home.

Whether you choose to explore or simply relax and unwind, today is all about enjoying the laid-back vibe of this lovely town. There are some optional excursions which we are happy to arrange. Perhaps a visit to a historic paper mill, where they produce stunning Japanese washi paper?

Early evening, we’ll regroup for a sake tasting. Sake is Japan’s iconic rice wine, and Uchiko is the perfect place to try it. You’ll then be free to head into town to dine at one of the many local restaurants.

/ Accommodation: Traditional houses in Uchiko
/ Meals included: Breakfast (Lunch & Dinner are own arrangements)

DAY 6 - Monday October 19

Uchiko to Uwajima – Uwa Kai Coastal Riding

After a short drive south to the town of Uwa, we’ll continue our Shikoku adventure with a ride to the port town of Uwajima. Today’s route is challenging (75km but almost 1k in climbing) but incredibly rewarding, with stunning views of the Uwa Sea and terraced orange orchards clinging to the hillsides. It’s Shikoku at its most beautiful.

Uwajima is a lively port town with a rich history and a laid-back feel. After arriving, you’ll have time to explore before we gather for a sunset happy hour (weather permitting) and another delicious dinner featuring fresh local seafood.

Team Macchiato: Team Mac visit nearby Ozu City. They’ll take a stroll through the old streets and enjoy an optional river cruise on a traditional boat. Afterward, they’ll head to the Uwa Sea to visit Doi Shunju, a pearl jewellery workshop, where they can learn about the art of pearl cultivation and even pick up a unique souvenir. They’ll then make their way to Uwajima to reunite with the cyclists for sunset happy hour and dinner.

/ Accommodation: Uwajima Hotel
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

DAY 7 - Tuesday October 20

Uwajima to Cape Ashizuri – Ride to the Cape

It’s our queen stage. Door to door is 130km and 1500VM. It’s also the most spectacular ride of the trip. We head inland and make our way down to Cape Ashizuri, where the Uwa Sea meets the Pacific Ocean. This is Shikoku’s rugged southern tip, and it’s as dramatic as it sounds.

The route takes us through rolling hills, quiet countryside, and along coastal roads with jaw dropping views. Cape Ashizuri itself is wild, remote, and incredibly beautiful. After arriving, you’ll have time to explore the area, including the iconic Ashizuri Lighthouse and Kongofukuji Temple, one of the 88 temples on the Shikoku Pilgrimage.

Team Macchiato: While the cyclists are out tackling the ride to Cape Ashizuri, Team Mac will start their day with a morning stroll through the beautiful Nanrakuen Japanese Gardens. They’ll then visit the Satoumi Aquarium, where they can learn about the unique marine life of the Uwa Sea. Afterward, they’ll travel to Cape Ashizuri, where they’ll explore the lighthouse, take a scenic coastal walk, and visit Kongofuku-ji Temple. They’ll reunite with the cyclists at the accommodation for a well-deserved dinner.

/ Accommodation: Cape Ashizuri Hotel
/ Meals Included: Breakfast & Dinner (Lunch is own arrangements)
  

DAY 8 - Wednesday October 21

Cape Ashizuri to Shimanto – River Riding

Cycle Distance: 80km | Elevation Gain: 400m

Yesterday was a biggee so todays 80km ride should be looked at as recovery. The good news is that it’s almost flat. (Almost!!)

We leave the rugged beauty of Cape Ashizuri and follow the Pacific Ocean until we reach the mighty Shimanto River. Known as “Japan’s last clear stream”, the Shimanto is famous for its pristine waters and peaceful scenery. Our route follows the river’s winding path, taking us through lush green valleys, past traditional fishing villages, and over charming wooden bridges. It’s a relaxed and scenic ride, perfect for soaking in the beauty of rural Shikoku.

Team Macchiato: While the cyclists are out riding along the Shimanto River, Team Mac will visit Nakamura Town. Here, they’ll have the option to hire a Japanese shopping bike (mamachari) and take an easy cycle along the river to one of the iconic submersible bridges. After lunch at a local restaurant, they’ll make their way to Shimanto to reunite with the cyclists for dinner.

/ Accommodation: Shimanto Hotel
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

Day 9 - Thursday October 22

Shimanto to Tosa-Kure – Ride to the Coast

Cycle Distance: 95km | Elevation Gain: 600m

Today, we continue following the Shimanto River to its source, then head over the hills and back to the Pacific coast. It’s a mix of river valleys, forested climbs, and coastal roads, with plenty of stunning views along the way.

Our destination for the night is Tosa-Kure, a charming coastal town with a fantastic fish market. After arriving, you’ll have time to unwind at our beautiful accommodation before enjoying another delicious dinner featuring fresh seafood and local flavours.

Team Macchiato: While the cyclists are out riding to Tosa-Kure, Team Mac will visit a beautiful local gorge for a scenic morning walk. In the afternoon, they’ll leave the van for a scenic train ride on the Yodo Sen Line to Kubokawa, where they’ll be picked up and taken to the accommodation in Tosa-Kure. They’ll reunite with the cyclists for dinner.

/ Accommodation: Tosa-Kure Hotel
/ Meals included: Breakfast & Dinner (Lunch is own arrangements)

DAY 10 - Friday October 23

Tosa-Kure to Kochi – Ride to Kochi City

Most of you should take a rest day tomorrow prior to the Fondo on Sunday. It’s probably a good idea to also be gentle on your legs today. It’s only 65km as we follow the Pacific coast to Kochi City, the lively capital of Kochi Prefecture. The ride is a mix of coastal roads, rolling hills, and a few challenging climbs. Kochi City is known for its vibrant atmosphere, historic castle, and delicious street food.

Tonight is a free evening to explore Kochi at your own pace. You might want to check out the famous Hirome Market, a lively night market filled with local eateries serving everything from fresh sushi to grilled seafood.

Team Macchiato: Team Mac will have time in the morning to explore the small seaside town of Kure. They’ll then follow the cyclists’ route, stopping at highlight points along the way. They’ll arrive early in Kochi City to explore the markets and shops before reuniting with the cyclists for the evening.

/ Accommodation: Kochi Hotel
/ Meals Included: Breakfast (Lunch & Dinner are own arrangements)

PS, 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.

DAY 11 - Saturday October 24

DAY 12 - Sunday October 25

Imabari – Cycle Shimanami Event

We planned the whole itinerary around today. It will be a trip highlight as you tackle the Cycle Shimanami event which is run every 2^nd year.

This iconic ride takes you back across the Shimanami Kaido, but this time on the expressway (closed to cars for the day) with thousands of other cyclists from Japan and around the world. Please don’t treat this as a race. You should be looking at it as a great day on the bike with a few thousand friends on protected roads.

You can choose from various distance options, ranging from a relaxed 40km to a full 140km. Whatever you decide – it’s a magnificent way of finishing our trip together.

Tonight, let’s celebrate our final dinner together. No doubt, there will be stories to tell. It’s been a fantastic 2 weeks.

Team Macchiato: While the cyclists take on the Cycle Shimanami Event, Team Mac will head into town for a Japanese cooking lesson. They’ll learn how to prepare traditional dishes and enjoy the fruits of their labour for lunch. Afterward, they’ll visit the Imabari Towel Museum to learn about the history of this unique industry. They’ll reunite with the cyclists in the evening for the final group dinner.

/ Accommodation: Imabari Hotel
/ Meals included: Breakfast, Lunch & Dinner
 

DAY 13 - Monday October 26

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. The train station is really close (as in walking distance) but the airport is further away. Robbie will be heading there so you are very welcome to join her.

Finally – on behalf of Ride Holidays and We Ride Japan – 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,

Karl, Robbie, Will and the team  

/ Meals included: Breakfast