Embark Day — Every great voyage deserves an opening scene, and Athens provides one that is almost impossible to forget. The Acropolis glows above the city, ancient stones catch the afternoon sun, and narrow lanes lead from classical ruins to candlelit tavernas with the ease of a dream.

In October, Athens feels especially graceful—warm, luminous, and alive without the press of high summer. Arrive early for our Athens PreTour and let the city draw you in slowly: through myth and marble, rooftop views and neighborhood flavors, until the journey ahead feels like the continuation of a story that began long ago.

Day 2 — Your first cycling day begins in Ermoupoli, and it is a wonderful place to settle into the rhythm of the journey. Syros has a different personality from many of the Cycladic islands — less flashy, more lived-in, with elegant old buildings, busy cafés, church domes, marble squares, and a harbor that still feels like the heart of the island.

You’ll roll out from town and gradually leave the neoclassical waterfront behind as the route carries you toward Ano Syros, the historic hilltop village above Ermoupoli. From there, the island opens up beautifully, with views across the Aegean and a real sense that you’re discovering Syros from the inside rather than just visiting its shoreline.

As the ride continues west, the day becomes more relaxed and coastal. You’ll pass through or near some of the island’s favorite beach communities, each with its own easygoing charm. This is the kind of ride that gives you a little bit of everything on the first day: a handsome harbor town, old village lanes, blue-water views, seaside pauses, and enough time off the bike to enjoy where you are.

By the time you return to Ermoupoli, you’ll understand why Syros is such a fantastic opening ride. It is beautiful without feeling overdone, active without feeling rushed, and full of the small, memorable moments that make island cycling so rewarding.

Day 3 — This is one of those rides where the day keeps opening up as you go. You’ll start right in Kusadasi, with the harbor behind you and the Aegean close by, before easing out of town toward the inland roads that lead to one of the great ancient places of the Mediterranean. It’s a wonderful first impression of this part of Turkey: a little seaside energy, a little countryside, and then suddenly the weight of history waiting just ahead.

Ephesus is the centerpiece, and it deserves the time. You’ll step away from the bikes and into a city that once stood at the center of ancient life in this part of the world. Here you’ll have time to take in the scale of it all: the old marble streets, the theater, the columns, the carved details, and the sense that people have been gathering here for centuries.

After Ephesus, you’ll roll into Selçuk for a relaxed pause before the return to Kusadasi. Instead of a fixed lunch, you’ll have the freedom to do what feels right: pick up a snack, settle into a café, enjoy a cold drink, or simply take a short wander through town. Cyclists who prefer to wait can head back to the ship and enjoy a late lunch aboard. It keeps the day flexible and comfortable, with enough structure to make the ride flow and enough breathing room to let you enjoy the place on your own terms.

Day 4 — You’ll leave Mitilini from the water’s edge, rolling away from the ship as the harbor begins to settle behind you. The town has that layered Aegean feeling — practical, lived-in, beautiful without trying too hard — and the ride gives you time to notice it before the streets begin to loosen into the quieter roads toward Moria. This is where Lesvos starts to reveal itself at bicycle speed: olive trees, low stone walls, village corners, and the easy rhythm of an island that has been shaped by farming, sea trade, and time.

The Roman Aqueduct at Moria is the first real pause of the day, and it’s worth taking your time with it. The old stone arches rise out of the landscape in a way that feels both humble and impressive, especially after you’ve arrived there under your own power. From there, you’ll continue into the Moria area for a simple olive grove stop, where you can taste local olive oil among the trees and get a feel for one of the island’s everyday traditions. It’s not a rushed tasting or a formal production — just a chance to slow down, enjoy the setting, and taste something that belongs to this place.

From Moria, we’ll turn back toward Mitilini and return along the coast, bringing the Aegean back into the ride. You’ll ride to the gates of Mytilene Castle, one of the great landmarks of the city. Set above the harbor, its walls have watched over this corner of Lesvos through Byzantine, Genoese, and Ottoman chapters of the island’s history. You’ll have time to walk, look out over the water, and feel how the castle connects the town, the port, and the island’s long story.

Day 5 — Bozcaada is one of those islands that feels made for exploring by bike. You’ll start right near the harbor, where the town has that easy Aegean rhythm: fishing boats, stone lanes, café tables, and the castle watching over it all. Before the ride really opens up, you’ll pause at Bozcaada Castle, a sturdy old landmark that gives you a sense of how long this little island has been looking out over the sea.

From there, the ride slips out of town and into the quieter side of Bozcaada. The roads move through vineyard country, with open views, dry island light, and the occasional glimpse of blue water pulling you forward. It’s not a day about rushing from one landmark to the next. It’s about enjoying the feel of the island as it changes around you — town to countryside, vineyards to coast, and then down toward Ayazma Beach.

Ayazma gives you a beautiful reason to stop. You’ll have time to take in the water, the beach, and the relaxed south-coast atmosphere before turning back toward town. And just before returning to the ship for lunch, we’ll finish with a local wine tasting. It’s a fitting Bozcaada ending: a few pours, a little island flavor, and a chance to settle into the moment before rolling back to the harbor.

Day 6 — Istanbul has a way of making history feel close, not distant. For this day, you’ll trade cycling shoes for comfortable walking shoes, because the best way to experience this part of Istanbul is with a professional guide leading you through the old city at a lively yet thoughtful pace. You’ll have time to step inside, look around, ask questions, and enjoy the city’s color and warmth.

You’ll leave the ship and cross into the historic peninsula, where the streets seem to hold pieces of every era: Byzantine vaults, Ottoman gates, market arcades, palace gardens, and the everyday rhythm of people moving through it all. It feels layered and full of personality, but also welcoming — a place of tea, conversation, craftsmanship, and hospitality.

The morning begins beneath the city in the Basilica Cistern. It’s quiet, cool, and beautifully atmospheric, with rows of columns reflected in shallow water. After the brightness of the waterfront, it feels like stepping into one of Istanbul’s hidden rooms. Back above ground, the city opens up again around Hagia Sophia and Topkapi Palace, where the scale of the old imperial capital becomes easier to understand.

What makes the day especially enjoyable is the way the major sights are balanced with local texture. You’ll notice the smell of roasted chestnuts, the clink of tea glasses, the colors of tilework and carpets, the sound of vendors calling from nearby streets. Lunch is a chance to pause together, enjoy Turkish flavors, and let the morning’s impressions sink in.

The Grand Bazaar brings a lively finish to the day. Its covered lanes are full of movement and detail — lanterns, spices, leather, ceramics, gold, textiles, and conversations happening in every direction. You don’t need to buy anything to enjoy it; simply wandering here is part of the experience. By the time you return to the ship, you’ll have had a generous taste of Istanbul’s history, beauty, and personality, all within a day that feels full but not rushed.

Day 7 — Your day begins with a short ferry ride from Çanakkale to Eceabat, which gives the morning a relaxed and memorable start before you even get on the bike. You’ll cross the Dardanelles with the waterfront behind you and the Gallipoli Peninsula ahead, watching the coastline come closer as the day begins to take shape.

Once you roll out from Eceabat, the ride settles into a wonderful rhythm. The peninsula feels open and peaceful, with quiet roads, low hills, rural villages, and long views that shift between countryside and sea. October is a lovely time to ride here, with softer light, cooler air, and a more comfortable pace along the coast.

As you continue toward Alçıtepe, you’ll notice the simple charm of the area: village cafés, local life moving at an easy pace, and roads that let you experience Gallipoli slowly rather than rush through it. From there, the ride continues to the Çanakkale Memorial, a powerful place to pause above Morto Bay and take in both the view and the history of the peninsula.

After the memorial, you’ll ride back toward Eceabat, with the Dardanelles gradually returning to view. Cyclists who want a longer day can continue along the quieter western side of the peninsula, where the scenery feels more remote and the roads offer a deeper look at Gallipoli’s coastline and countryside.

Day 8 — The morning starts along the Chios waterfront, with the port behind you and the Aegean beside you, as the route heads north toward Vrontados. At Daskalopetra, you’ll stop near a place long associated with Homer, and whether you come for the mythology or simply the view, it’s a fitting way to begin a day on an island with such deep layers of history.

The ride’s most memorable stretch comes later, as you move into Kampos. This area feels almost made for cyclists: narrow lanes, old estate walls, citrus trees, small churches, and elegant houses that hint at the island’s former wealth without feeling staged.

You’ll notice how different it feels from the harbor — softer, greener, more private. It’s a lovely place to slow down, talk with other participants, and enjoy the kind of details you would miss from a bus window.

After a local refreshment stop, the route continues toward Karfas, where the beach and coastline bring the ride back to the Aegean.

Day 9 — Our cruise disembarks in Laurium, which sits along the southeastern coast of Attica, close to Cape Sounion, and highly convenient for departures from Athens International Airport. To make disembarkation easy, our included shuttle will take participants directly from the ship to Athens International Airport. From there, travelers flying home can proceed with their departures, while those who wish to continue exploring Greece have a convenient option: Athens Airport offers baggage storage in the arrivals area, allowing guests to leave their luggage securely before heading into Athens or onward to another Greek destination.

We’ve chartered La Belle de l’Adriatique for Santana’s 2027 Athens & Istanbul 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.