Top Cyclades Islands Sailing Tours

Go on a half-day, small-group sailing adventure in the Aegean Sea. Select your preferred departure time—morning or afternoon—and set sail for Mykonos’ south coast or to the mythical birthplace of Apollo on the island of Delos. Relax at the beach, snorkel in beautiful turquoise water, and marvel at Delos’ ancient archaeological site. Enjoy lunch or dinner, wine, and hotel pickup and drop-off included in the tour price. Upgrade to a private boat for a personalized experience.

Experience the volcanic beauty of the Aegean without having to line up for selfies on land during a sunset catamaran cruise. Plus, sailing at golden hour reveals the scenery when it looks most stunning. You'll stop to bask on Santorini’s red- and white-sand beaches, snorkel, and soak in volcanic hot springs. With included hotel transport plus a fresh Greek barbecue and soft drinks, beer, and local wine served onboard, it's a decadent way to enjoy the island’s famous sights.

Escape the crowds on land and admire Mykonos from the water on a luxury catamaran cruise that takes you off the beaten path to Rhenia, an uninhabited island surrounded by crystalline waters and home to ancient Greek ruins. Enjoy free time to relax as you wish—swim in the crystal-clear waters, soak up the sun, and enjoy refreshing drinks on board. Note: the itinerary is subject to weather conditions and might be adjusted to explore the southern coast of Mykonos.

Set sail on an adventure that combines history and relaxation. Cruise from Mykonos to Rhenia, admiring the sea views along the way, then explore the ancient ruins of the Archaeological Site of Delos on a guided tour. Take the opportunity to swim or snorkel in Rhenia’s turquoise waters. Everything you need is included: a freshly prepared Greek lunch, beverages, snorkeling gear, and floatation devices.

Experience the Aegean in style on this sailing trip from Santorini aboard a luxury catamaran. Start by heading out to the volcanic area just off of Oia, with plenty of time to soak in the hot springs before moving on past the Venetian Lighthouse. Then stop at the White Beach to swim while the crew prepares a sumptuous barbecue of meats, seafood, salads, and local white wine. Set sail for Red Beach, where wrap up your experience with more swimming and cocktails.  The sunset sail follows the same itinerary in reverse.

Make the most out of your time in Santorini aboard this tranquil catamaran tour. Enjoy the splendid views from the boat as it sails around Santorini, and discover a side of the island many other visitors miss. Swim and snorkel in the blue sea and indulge in a delicious barbecue dinner prepared onboard, complemented with local drinks. You see the best of the island in one relaxing getaway.

Discover a side of Santorini that few other visitors get to experience—and make exploring beyond the mainland easy—on this half-day tour. Look forward to visiting Santorini's unique volcanic landscapes, and head to two islets accessible only by boat. Sail to Nea Kameni to hike up to the crater of the active volcano (entry tickets own expense), and to Palea Kameni, where you can soak in natural hot springs.

Join this boat trip to the South Pirate Caves, where you will enjoy some local white wine and seasonal fruit and snorkelling in the very famous blue lagoon on the Fira channel of Paros, crystaline turquoise water with extreme visibility!

Take a cruise out to the caldera of Santorini aboard a catamaran and spend some time checking out the island's colorful beaches with this tour. You'll have time to swim at Red Beach and soak in the hot springs at the caldera of Santorini, with time left over for swimming and an included lunch or dinner at Mesa Pigadia Beach.

Cruise around Santorini on this half-day catamaran tour departing from Vlihada Marina. Observe famed sights such as the Venetian Lighthouse, the Indian Rocks, the Red Beach, and the White Beach as you glide atop clear blue water. Enjoy a swimming and snorkeling excursion, then take in panoramic views of Thirasia Island and, if you've chosen an evening tour, sail past Oia during sunset—a must-do for any Santorini trip.

Santorini stuns at any angle, but its most magical destinations are often only reachable by water. Experience its rugged coastline and volcanic islands by boat on this catamaran cruise. Choose between daytime and sunset bookings; snorkel equipment is available for swim stops, and you'll enjoy a BBQ buffet lunch or dinner washed down with local white wine and soft drinks—as well as swimming to the Santorini Hot Springs.

Set sail for the ultimate escape with this Rhenia-Delos cruise, where you’ll leave the crowds of Mykonos behind for a day of serene adventure. Swim, sunbathe, and enjoy the lush beauty of Rhenia Island before indulging in a traditional Greek barbecue on board. Then, explore the mythic Delos Island—wander historic archaeological ruins (entry at your own cost) or relax on its peaceful beaches, the choice is yours.

With its rugged arches and caves, Kleftiko Beach is one of Milos’ star attractions. Skip the long hike down and up and see it from the water on this intimate cruise with swim stops en route—and snorkeling gear included so you can make the most of the crystal waters. An open bar gets the party spirit flowing, while an authentic Greek lunch keeps you energized.

With its caves and sea arches, Kleftiko Beach is one of Milos’ most in-demand locations. See it in style when you book this catamaran cruise, with meals, snacks, and drinks included plus snorkeling gear, fishing kit, pool noodles, and stand-up paddleboards (SUP) to entertain you. Choose between morning and sunset cruises, and upgrade to include transfers: You can also make lifetime memories with a private cruise just for your group.

Book your Santorini sailing tour to explore the volcano, hot springs, stunning views, and local flavors!

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers, as the boat tour begins at the port of disembarkation.

Milos is renowned for its stunning Aegean coastlines, but many of the island’s most spectacular sights are only reachable from the water. Spend the day out on the open sea during this full-day small-group sailing and snorkeling excursion, covering Milos’ western side. Tours include five get-down stops, from the volcanic sands of Kleftiko Beach to the bay of Agios Dimitrios. Top it off with Breakfast, alcoholic drinks, and a traditional Greek lunch.

Indulge in the ultimate day of fun in the sun on this full-day sailing trip to ancient Delos island, a UNESCO World Heritage Site. You also stop in scenic Rhenia Island for a refreshing swim and snorkeling session in sparkling, sun-dappled waters. A freshly prepared BBQ lunch is included, and you can upgrade to include door-to-door hotel transfers.

Our Santorini day cruise starts from the picturesque port of Vlychada, sailing onwards to explore the beauty of the Red Beach, White Beach, Indian Rocks, and the historic Venetian Akrotiri Lighthouse. Our first stop is at Mesa Pigadia Beach, nestled the island's southern reaches. Here, you can dive into the crystal-clear waters for a refreshing swim and some snorkelling fun. The real highlight of our journey lies ahead as we venture into the awe-inspiring Caldera. Our next stop? The renowned Hot Springs of the volcano, where you can enjoy a rejuvenating swim in the therapeutic waters. For our third stop, we offer you the chance to visit and swim in Thirasia, the island adjacent to Santorini. After your swim , indulge in our elaborate lunch with stunning views of the surrounding seascape. As we sail back to Vlychada, don't miss the perfect opportunity to capture the breath-taking beauty of the Caldera. The ideal conclusion to your cruise, offering you the best views of Santorini.

A full day of fun, culture and culinary discovery. Spend a perfect day out on the sea combining a relaxing sailing cruise, swimming and sunbathing at the secluded and pristine beaches of the uninhabited island of Rhenia with a visit to Delos island – one of the most important archaeological sites of Greek history and a UNESCO world heritage landmark.

Spend the day sailing around beautiful Santorini on a catamaran. Imbibe unlimited amounts of white wine, soft drinks, and water and indulge in a delicious barbecue prepared onboard the catamaran as you sail in the gorgeous blue waters of the sea off the shore of Santorini.

The island of Mykonos has many views that can only truly be appreciated from the water. On this half-day small-group cruise, hop aboard a catamaran and admire Mykonos’s whitewashed houses in the distance as you circle the island and visit nearby landmarks. After arriving at nearby Rhenia, dive into the crystal clear waters of a secluded cove for a refreshing swim.

Sail along the Milos coastline and take in views of Klima’s colorful ‘Sirmata’ houses as well as the villages of Skinopi, Areti, and Fourkovouni on this full-day catamaran cruise setting out from Adamantas. Explore geological marvels, such as the Arkoudes lava rocks, and jump into the warm ocean waters for a swim in secluded island bays.