Tokyo is a dazzling fusion of ancient tradition and futuristic sophistication. Where else can you witness a centuries-old festival just steps away from a robot serving cocktails under a life-size Godzilla? Tokyo doesn’t choose between eras—it harmonizes them. You’re not walking through history or chasing the future. You’re existing in both, simultaneously.

Embark Day — Our 11-day Odyssey begins in Tokyo, where our cruise will embark from the Yokohama Cruise Terminal. If you care to arrive a couple of days before embark, our optional non-cycling Tokyo PreTour includes shuttles, a perfectly-sited hotel and a fast-paced overview of this signature city—a perfect konnichiwa to Japan. On embark afternoon we’ll assemble and test our bikes (or accept an optional rental bike) at the pier. Flight arrival details will be sent out a year prior to the cruise.

Day 2 — On the first morning of our cruise you’ll wake up in Fuji, a town at the base of Japan’s iconic volcano. Our tour was carefully timed to allow a keepsake photo of you, your bike and Mt. Fuji, all framed by cherry blossoms.

Our easy coastal warm-up ride along the lightly-traveled Izu Peninsula takes us past a famous Shinto shrine, where we’ll obtain an introduction to Japanese spiritualism that will help us to better understand Japan and its mysterious culture.

Today’s featured site is a guided visit to the magnificent Numazu Imperial Villa. Built in 1893 the villa served as the Emperor’s beachfront summer retreat for seven decades. Many will continue along a rugged and remote coast, where some will reach Cape Ose. No matter how far you choose to ride, your return route features stunning views of Mount Fuji.

Day 3 — Following a second luxuriously restful night aboard, we arrive at Shingu, a national pilgrimage center known as the Gateway to the Heavens. Our first stop of the day is at Kumano Hayatama Taisha, one of the three legendary Kumano shrines.

From there, we’ll take the stunning coastal road east to the iconic Nachi Falls — the tallest in Japan, set behind the picture-perfect pagoda of Seiganto-ji Temple.

Afterward, we’ll roll into Nachikatsuura, a fishing port that serves up top-notch sushi and steaming udon noodles — perfect fuel for the next stretch.

Heading inland, we’ll ride through quiet valleys toward the Kumano River Gorge, the rhythm of your pedal stroke syncs with the flow of the water beside you. Your highlight? The towering Otorii Gate at Kumano Hongu — a 110-foot symbol of ancient pilgrimages. Looping back through country roads, we’ll wrap up the day with a breezy return past Asuka Shrine.

Day 4 — Today we’ll roll out of Kochi harbor at dawn, the morning sun shimmering on the Pacific. The day begins on the famed Yokonami Peninsula, following the Kurushio Line, a gentle ribbon of asphalt that hugs the sea.

With the breeze at your back, you cruise past cliffs and fishing hamlets until Dragon Beach comes into view—perfect for a quick pause, some fresh air, and a group photo with a few new friends. Next, we’ll ride amongst lush pine trees on our way to Shoryu Temple where a short peaceful encounter lets you soak up centuries of temple lore and serenity.

After receiving a blessing to help guide your continued journey of Japanese discovery, our return route to the ship will visit a prime example of Japan’s “Magnificent Seven”, Kochi Castle. One of Japan’s few original castles with its main keep and inner citadel still fully intact. Set atop Otakasa Hill, it’s an iconic destination that offers sweeping views of the city, and a samurai museum.

Day 5 — In the coastal hush of Uwajima’s April bloom, your wheels hum beneath you as castle rooftops pierce the sky above blooming cherry blossoms. Uwajima Castle, regal and rare, rewards a shirt ascent with timeless views of the bay below.

From here, your route scrolls like calligraphy along Shikoku’s Coastline—through fishing villages, citrus orchards, and fields of Sakura. As our route emerges onto the coast, you’ll find yourself at a pearl plantation where you’ll meet biologists, divers, and artisans.

As we return to Uwajima, we’ll pause at a local foodies seeking an authentic bite will be rewarded with fresh seafood, bento, chicken yakitori, and citrus mochi. Others will stroll through the adjoining market, alive with local crafts and smiling merchants. Our final stop of the day, a serene visit to Ryuko-in Temple, where incense drifts past the ancient stone lanterns.

Day 6 — The sun rises over Hakata Bay as your tires whisper across Fukuoka’s harbor streets. You’ll trace Japan’s northern shore on a quiet bike path hugging the coastline beneath pink cherry blossoms ushering you toward Genkai National Park.

There, a short pause reveals dramatic cliffside views of the Genkai Sea—a meditation spot favored by the local Buddhist monks.

By midday, the spires of Karatsu Castle invite you to ascend the winding path traveled by centuries of Samurai to explore its feudal history and commanding bay views. The final stretch takes you through Nijinomatsubara, where you’ll ride through the forest of one million pines.

Ready for a night out? As our ship will overnight in the relatively quiet town of Karatsu, this is your chance to mix an evening stroll with local dining.

Day 7 — A second day of riding in this particularly beautiful section of Japan’s westernmost main island starts with a ride from Karatsu to Yobuko, where we’ll walk our bikes through the center of the Cinderella-like village where they close their main street for a festive morning market that disappears when the clock strikes Noon.

The return route loops through Nanatsugama Park, where we’ll park our bikes to explore a geologic wonderland. Those who invest in more miles of pedaling will be rewarded with a loop through terraced rice paddies and a hop to Takashima Island, where Mother Nature’s Kamikaze (or Divine Wind) saved Japan from a pair of 13th-century Mongol invasions by destroying the invincible fleets of Kublai Khan.

Day 8 — After an overnight crossing, we’ll wake up for a one-day visit to a different country! Because our cruise ship is foreign-flagged, Japanese maritime law requires our itinerary to include a foreign port. After scouting and testing a pair of more famous alternatives, for 2027 we chose the South Korean port of Yeosu for a fortuitous day of sights and cycling.

Your journey begins in the harbor city of Yeosu—once a sleepy port, now the backdrop to a day steeped in nature and tradition. The morning fun begins with the Yeosu Ocean Rail Bike, a rare chance to glide above the surf. Rolling forward, you arrive at Odongdo Island, where centuries-old camellia groves whisper with history and the sea laps quietly along the rocky shore.

After descending, you’ll cross a small suspension bridge to descend into Dolsan Park, where the city’s layers unfurl beneath you. We’ll catch the cable car for a breathtaking view of this coastal city, whether you ride down or take the cable car, we’ll regroup at our yacht size cruise ship to set sail while enjoying a dinner inspired by our day in South Korea.

Day 9 — The ride begins on the shores of Yamaguchi Prefecture, where the narrow streets of Shimonoseki open up to waterfront bike paths. Our route traces the coast to reach a small fishing village where traditional shrines, harbor views, and grilled oysters offer an authentic experience.

As the sun stretches toward the afternoon, we’ll ride past the vermillion Akama Shrine perched over the bay before coasting back to the ship. We’ll take in the tranquil ocean views as we head South to Kaikyo Yume, a glassy observation deck with panoramic views over the Kanmon Strait.

Day 10 — Our big finale—Japan’s famous Shimanami Kaidō bike path. You’ll begin your day in Imabari with a gentle breeze off the Seto Sea and glide across the majestic Kurushima Kaikyo Bridge, a 4-km engineering wonder built specifically with cyclists in mind—wide lanes, spectacular views, and no cars! At Kirosan Observatory, a scenic detour rewards you with handmade onigiri from a roadside shop as you soak in the views of Setouchi.

Around midday you’ll roll into Ikuchijima for a cultural surprise: the majestic Kosan-ji Temple, underground caves, and a surreal marble stairway to heaven.

This afternoon we’ll arrive back to the ship in time to pack our bikes and stroll through Senkoji Park for some citrus gelato before saying farewell to Onomichi.

Day 11 — After a tenth night aboard our cruise disembarks in Osaka, where our tour includes the short shuttle to Osaka’s KIX airport, which hosts over a dozen daily nonstops to America’s West Coast. For those who want to linger, we will be offering an Osaka PostTour—the combination of attractions in Osaka and nearby Kyoto can’t be topped.

If Tokyo is Japan’s polished diplomat, Osaka is the charismatic cousin who shows up late and steals the show. The buildings lean with history and the shopkeepers greet you like family. There’s a winking confidence to this city—It knows it’s the fun one.

Osaka is joy with a Kansai accent. You’ll hear it in the comedy clubs of Namba, in the banter between friends at market stalls, in the clink of highballs in smoky izakayas. This is a city where humor and hospitality go hand in hand—where being welcomed feels easy.

Santana Adventures is proud to announce that we have chartered Windstar’s brand-new all-suite Star Seeker for our 2027 Japan Cycling Cruise!

The Star Seeker is an ALL-SUITES yacht! The smallest suite is twice as large as staterooms found on other new cruise ships.

The Star Seeker has 17 different suite categories which provide plenty of options to suit every preference.

Every suite has an exterior view, and over 90% of the suites have either a balcony or floor-to-ceiling “infinity” windows.

All staterooms have independently controlled thermostats, sound proofing, flat-screen tv, mini-fridge, and resort-style bathrooms.

The Star Seeker has a 1:1.5 crew-to-passenger ratio to provide award winning service.

4 gourmet restaurants provide a variety of fresh culinary options — in addition to 24-hour complimentary room service!

Santana has worked with Windstar since 2010. With this win-win relationship, Santana obtains the lowest pricing and best availability. Their yacht-sized fleet allows Santana’s charters to use small ports that are better suited for cycling. We’ve now worked with Windstar to create custom-for-cycling itineraries in the Mediterranean, Tahiti, British Isles, Australia, New Zealand, Norway, the Baltic Sea, and Japan!

Santana and our participants love the intimate size of Windstar’s yachts, as does the cruising public and industry critics. Year after year, Windstar wins all the major awards for small ship cruising, and scores the highest return-client loyalty.

The Star Seeker is Windstar’s newest yacht, so new in fact that it won’t be in the water until December 2025. We are ecstatic to be one of the first to charter this incredible new small cruise ship, and we know you’ll share our enthusiasm about all of the brand-new five-star amenities.