Top Cyclades Islands Sailing Tours

Many of the sights near Mykonos can only be enjoyed from the water. Admire the island’s whitewashed houses in the distance as you sail through the Aegean Sea on this private half-day catamaran cruise. Enjoy a glass of wine as you sail by Baos Pirates Island, and dive into the crystal clear waters for a swim after dropping anchor in a cove off the coast of Rhenia.

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.

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.

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.

Explore the Aegean island of Milos on this sailing excursion. Enjoy a small group experience with up to 12 passengers that includes visits to Cape Vani, Kalogries Beach, and Agios Dimitrios bay. Check out the caves of Kleftiko and Sykia by dinghy, go swimming and snorkeling, and relax by the sea. Enjoy complimentary lunch, snacks, drinks, access to snorkeling equipment, and GoPro photos.

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.

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!

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.

Enjoy a relaxing day cruising in a catamaran along the southern coast of Mykonos and to beautiful Rhenia Island. Visit places that would take much longer to get to independently. Spending the half-day cruise admiring the views, lounging on the sundeck, swimming, snorkeling, stand-up paddle-boarding, and kayaking. A delicious 3-course meal will be served on board, and the catamaran is even equipped with indoor showers so you can freshen up.

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.

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.

Set sail on an unforgettable luxury cruise aboard a Jeanneau 57 sailing yacht and discover legendary Kleftiko, one of Milos’ most iconic natural wonders. Departing from Adamas Port, this experience blends relaxation, adventure, and local storytelling in true Cycladic style. Sail along the stunning coastline, passing colorful Klima and the impressive Sykia Cave before reaching Kleftiko’s dramatic white rock formations, sea caves, and crystal-clear turquoise waters. Once a pirate hideout, the area is rich in history and volcanic beauty, with fascinating stories shared by your skipper along the way. Anchor in secluded coves for swimming, snorkeling, and stand-up paddleboarding, with time to explore caves and arches from the water. Back on board, enjoy a freshly prepared Mediterranean meal with unlimited drinks as you relax in comfort. Designed for small groups and authentic island vibes, this cruise is perfect for couples, friends, and travelers seeking a refined yet fun sea adventure.

Sail the deep blue ocean and stop for a dip in the ocean on this full-day cruise setting out from Antiparos on the Greek island of Paros. Relax on a sunbed aboard the traditional wooden vessel, or head out into the water for a swim before tasting traditional local delicacies such as marinated fish, ouzo, or wine.

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.

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.

Experience a calm and romantic trip to the amazing sites of Santorini on a charming wooden sailing boat! The peaceful atmosphere and gentle rocking of the boat provide the perfect backdrop for an unforgettable getaway, allowing you to fully appreciate the beauty and tranquility of this iconic sunset and volcanic landscape.

Milos is famed for its stunning, otherworldly coastal scenery, including the lunar-like Sarakiniko Beach— but the most impressive views aren’t reachable by land. On this small-group sailing tour, explore the island’s remoter west coast—a side of Milos most travelers miss—as you explore by boat. Along the way, listen to your skipper explain the island’s history and unique geology.

Many of Paros’s most popular sights can only be explored by boat. On this full-day tour, hop aboard a boat in the village of Pounda and set sail into the vibrant waters of the Aegean Sea. Explore off the coast of Antiparos and navigate the Padieronissia island complex, stopping at several sites for a refreshing swim in the warm ocean.

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.

Visit top sights along Santorini’s rocky coastline as well as two neighboring islands during this full-day sailing excursion. Enjoy a guided tour of the Santorini volcano, take a soak in the sulfur-rich hot springs of Palea Kameni, swim near the island of Thirassia, and watch the sunset just under the stunning village of Oia over dinner and wine.

With its caves and sea arches, Kleftiko Beach is one of Milos’ most spectacular locations. See it from the best vantage point—on the water—when you join this half-day catamaran cruise with a photo opp by Sikia Beach’s cave and a swim stop at Kalogries Beach. A fresh-cooked meal keeps the hunger pangs away, while water, soft drinks, beer, and wine keep you hydrated. Snorkeling gear lets you see the seascapes up close.

Swim, snorkel, and explore old pirate hangouts on this full-day group cruise to Milos and Polyaigos. Snacks and lunch, plus all sorts of alcoholic and non-alcoholic drinks are provided, so you don’t have to bring them yourself. This is a full-day of activity and relaxation, where your guide and crew make sure you have a great day out. Note that hotel pickup and drop-off are not included.

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.