Greece should be at the top of your list

Friendly locals that are happy to speak English and share their enviable Greek-island lifestyle. Great roads that link amazing sights, including some of the world’s finest archeological treasures. Clean air and a glass-like sea. The food is local, fresh, and healthy. The wine is light and refreshing.

Why haven’t your cycling friends flocked to Greece?

Although numerous Greek Islands offer a perfect day of sights and cycling, getting from one island to the next is a time consuming endeavor that, without use of a cruise ship, typically wastes an entire day or two between each island. Without a chartered yacht, this great week of rides would take over double the amount of time, and you’d only be cycling for half of it.

Our chartered yacht-dimension cruise ship is the sublime solution for a 9-day cycling adventure. A comfortable floating hotel that cruises from one carefully-selected island to the next while we sleep. A week of Greek Island cycling without a need for ferries or repacking.

Energetic cyclists will enjoy the morning climb from sea level, a chance to warm up while ascending out of a picturesque port. Others will opt for our morning boost, a short shuttle that gets you and your bike to a viewpoint that’s closer to lunch.

Embark Day – Our cruise starts and ends in Athens, the cradle of Western Civilization. Twice as old as Paris and half-again older than Rome, today’s Athens is safe, inviting, and vibrant.

Santana’s optional Athens PreTour is a great way to begin your Aegean Odyssey, and recover from a little jet lag. Our included shuttles from ATH airport and our PreTour hotel will take participants to our ship for embark.

After building our bikes, you’ll enjoy a glass of wine while our team goes over the route information for your next day’s ride.

Day 2 – Today is your first day of cycling, and Milos gives you a great introduction to the week ahead. You’ll roll away from Adamantas and quickly settle into the rhythm of riding on the island, with the harbor behind you and a changing mix of villages, volcanic scenery, and open views ahead. It’s a fitting place to begin, because Milos rewards you almost immediately with the kind of variety that makes exploring by bike so enjoyable.

Your first stop is the Catacombs of Milos, tucked into the hillside below Trypiti. You’ll step off the bike and into one of the island’s most remarkable links to its early Christian past, exploring underground galleries carved into Milos’ volcanic earth. It’s a quiet and unusual way to start the morning—and about as different from the next stop as you can imagine.

From there, you’ll cross the island toward Sarakiniko, where the scenery changes completely. Suddenly Milos turns white. Smooth volcanic formations roll toward the sea in sweeping folds and ridges, with brilliant blue water filling the channels between them. Leave the bike for a bit, wander over the rock, find your favorite viewpoint, and enjoy one of those places where the landscape itself is the attraction.

Then it’s back on the bikes for Pollonia, the small fishing village at the northeastern end of Milos. This is where the day slows down a little and you can make the time your own. Find a table by the water, grab a coffee, wander along the harbor, or choose one of the local cafés or restaurants if lunch sounds good.

If you’d rather keep things light and save your appetite, that works just as well. A late lunch will be available onboard when you return to Adamantas.

The final ride brings you back across Milos to the ship, wrapping up a first cycling day that gives you a little bit of everything along one of the most unusual coastlines in the Cyclades.

Day 3 – Crete has a way of making a bicycle feel like exactly the right form of transportation. The roads weave between olive groves, villages, mountains, and the sea, and there’s almost always something worth slowing down for—a bakery, a tiny chapel, a shaded village square, or a view that suddenly opens toward the coast.

The island also comes with a pretty impressive backstory. Crete was home to the Minoans, whose civilization flourished here thousands of years ago, and it occupies a starring role in Greek mythology as the birthplace of Zeus and the setting for the story of King Minos and the Minotaur. Later came Romans, Venetians, Ottomans, and generations of fiercely independent Cretans who helped shape the island you see today.

What makes cycling here special is that all of those layers sit right beside everyday island life. You’re not just riding between historic sites—you’re moving through orchards, farms, fishing towns, and villages that make Crete feel very much alive. And when the road eventually leads back toward the sea, there are few better ways to finish a ride than with the turquoise Mediterranean waiting ahead.

One of the best things about riding from Chania is how quickly the scenery changes. You begin beside the Venetian harbor with fishing boats in the water, cafés along the waterfront, and layers of old stone buildings packed into the streets behind them. Not long afterward, the harbor disappears from view, the roads become quieter, and olive trees and citrus groves start taking over the landscape.

Agia Lake breaks up the morning nicely, giving everyone a chance to stop and enjoy the greener surroundings before continuing farther inland. From there, the ride carries you toward Agia Kyriaki, where the monastery sits quietly in the countryside near Varypetro.

After visiting the monastery, you retrace the island northward and gradually find your way back into Chania. The final ride brings you through town to the ship, wrapping up a day that gives you a little bit of everything.

Day 4 – After yesterday’s ride through the quiet countryside around Chania, today shows you a very different side of Crete, with ancient history, vineyard country, and the Mediterranean all woven into the ride. You’ll begin by riding inland from Heraklion’s port toward Knossos, leaving the waterfront behind as the city gradually gives way to a more open Cretan setting. At the palace, you’ll have time to step off the bikes and explore one of the island’s most important archaeological sites before deciding just how much more riding you want from the day.

Cyclists looking for some extra miles can continue on the long-ride option into the Katalagari wine country, where the route carries you farther into the hills through vineyards, olive groves, and quieter rural roads. A stop at a local winery gives you a chance to enjoy this more agricultural side of Crete before turning back toward Heraklion. Those choosing the shorter route will start making their way toward the coast sooner, leaving a little more time for the afternoon.

Both routes eventually lead west toward Ammoudara, where the terrain settles down and the Mediterranean becomes the backdrop for the rest of the ride. This is a good place to stop for lunch, grab a coffee or something cold, or simply enjoy a little time near the beach before starting the final ride back toward town.

The day finishes beside Koules Fortress and the old Venetian harbor, where the massive stone walls, fishing boats, and waterfront give you one last change of scenery before the short ride back to the ship.

Day 5 – On the famous “volcano island” Santorini, we worked with local cyclists to map out the best rides. While we expected the challenging route would be scenic, the result was nothing short of spectacular.

The amazing views coasting across the hillsides hundreds over the royal blue water made it hard to keep our eyes on the road. As we want all of our participants to enjoy their day, and all routes of Santorini do require considerable climbs, we looked for an alternate option to capture the beauty of the island.

Our new friend Christos also had a plan for our participants who were willing to forgo a day of pedaling… and when a strong cyclist recommends a hike, we’re intrigued!

His non-cycling route passes through the string of cliff-top villages (with artists’ workshops and galleries) that cling to the remaining edge of the famous island that broke in two. Standing amongst the cliff-side ruins, you’ll peer into the caldera where Greek legends say the ruins of Atlantis fell into the royal blue waters.

Whether you hike or bike, today includes a luxurious sampling of Santorini’s wines from a vineyard with an unforgettable view.

Day 6 – My favorite island is Rhodes, home to one of the seven wonders of the ancient world. Today’s ride starts from a small fishing village where we’ll clip-in as the local fishermen are unloading the morning’s catch.

While long riders work up an appetite with a climb through pine forests to reach a coffee stop at Mussolini’s Chateau, the coastal route is just as scenic and reaches lunch with less time and effort.

Either way, everyone’s favorite array is at a villa where award-winning wines are the mainstay and spiced tsipouro is a tasty sideline.

While we are dining, the ship will move ahead to the island’s oldest port, where she’ll remain tied up at the main gate of the walled city of Rhodes until midnight.

After you finish your ride and clean up, local guides will meet us at the gate for an informative and fast-paced walking tour through the still thriving center of an ancient town that has never allowed cars.

While dinner is always served onboard, Rhodes is a foodie’s paradise, so why not find a dining spot to share with a few of your new friends?

Day 7 – From our many weeks of scouting and cycling Greece, my wife Jan’s favorite island is Kos, the birthplace of science and medicine. After pedaling away from Kefalos Bay, we’ll stop in a small village to tour the restored windmill that milled the flour for the fresh cookies that accompany our morning coffee.

After riding through a fir forest famous for peacocks, we’ll pedal through fields of grain interspersed with orchards of figs and olives. Before reaching old town Kos, we’ll learn about the island’s favorite son, Hippocrates, while enjoying guided tours of the Asclepeion, the birthplace of scientific healing. At the nearby Hippocratic Forum is a medical museum filled with ancient remedies and instruments.

As we enter old town Kos, our ride navigates the scenic palm tree lined bike paths before our tour of an oceanfront castle built in the 15th century to defend from raiders.

Day 8 – Our final morning of cycling is on Mykonos, where our routes pass legendary white sand beaches and pristine blue waters to reach a lighthouse and view of distant islands.

The return route threads through the lively dining and shopping district of “Little Venice” that surrounds a marina filled with expensive yachts. Re-boarding our own yacht late that morning, we’ll re-pack our bikes before a lunchtime cruise to the seventh island of our Greek Odyssey.

As we finish our meal, we’ll reach the island of Delos, the mythical birthplace of Apollo & Artemis. In a country that’s justifiably famous for marble temples and statues, this national park is the world’s finest showcase of antiquity.

Our expert guides will walk you through the streets of this ancient island sanctuary of the gods that was, for many centuries, a centerpiece of Greek culture. The evening’s farewell dinner as we cruise into the sunset is always a feast for the senses.

Disembark Day – We’ll arrive back in Athens on our final day, where our morning disembark and shuttles make it easy to take a flight out of ATH Airport in the late morning, or head over to our post-cruise hotel to enjoy a little more time in Greece.

We’ve chartered La Belle de l’Adriatique for Santana’s 2027 Greek Isles itinerary. A 110-meter (yacht-dimension) vessel outfitted with with advanced stabilization, ultra-green power plants, and Z-drive propulsion which enables it to pirouette within the small harbors that larger cruise ships can’t access.

Participants of Santana’s numerous charters of La Belle witnessed first-hand the distinctive capabilities of this specialized cruise ship, which made over half of the unique ports on our hand-tailored cycling itinerary possible.

Commissioned by CroisiEurope in 2007, this unique Belgian-flagged cruiser has just fewer than 100 soundproofed staterooms in five categories.

All have private bathrooms, spacious floor plans, king-width beds that can convert into separate full-width twins, individually-controlled A/C, and large view windows.

The floor plans of the A, B, C, & D Categories are identical, the only differences are the windows and which deck they are located on. A & B Staterooms have two large rectangular windows and are located on the top two decks. C & D Staterooms have two large portholes.

The cuisine is exceptional. Breakfast includes bountiful buffets created by our 5-star chef. Each evening your waiter will present a new five course menu—listing an array of choices for you to select from.

Is beer & wine included with dinner? Of course!

The Lounge has seating for all our guests and is a great place to relax, mingle with your fellow cyclists, catch up on emails, or read a nice book.

The bar, located on the Sun Deck, enjoys breathtaking 360-degree views.

Onboard Wi-Fi is included, as is expert wash-and-fold laundering of your valuable cycling wear.