Top Cyclades Islands Sailing

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.

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.

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.

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.

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.

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.

Experience the volcanic beauty of the Aegean without having to line up for selfies on land during a catamaran cruise. Stop to bask on Santorini’s red- and white-sand beaches, snorkel, and soak in volcanic hot springs. Choose to sail in the morning or at sunset when the scenery is washed in golden sun. 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.

The sea caves and swimming spots around Milos and Polyaigos are hard to reach without a boat and someone who knows the coastline. Cruise out for a full day of swimming, snorkeling, and exploring the old pirate coves, with the route and timing handled for you. Snacks, lunch, and drinks are all provided on board, so you can turn up and settle in while the crew runs the day.

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. Breakfast, lunch, and snacks are included.

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.

Get ready for an incredible Santorini Sunset Catamaran Cruise! Our adventure kicks off from the charming port of Vlychada , where we'll sail through the Aegean Sea. Along the way, we'll feast our eyes on famous spots like the Red Beach, White Beach, Indian Rocks, and the historic Venetian Akrotiri Lighthouse. Red Beach, or Mesa Pigadia Beach, is our first swim stop, where you can dive into the crystal-clear waters for a swim and snorkelling fun. Then, get ready for the highlight of the trip as we enter the breath-taking Caldera. We'll pause at the famous Hot Springs for a rejuvenating sulfur-rich water swim, followed by a visit to the nearby island of Theresia for more exploration and relaxation. Here you will treat your taste buds to a delicious Greek meal & Drinks while soaking up the panoramic views. As we sail back to Vlychada, unwind and soak in the magic of the most beautiful sunset, completing your Sunset Cruise with a serene and unforgettable experience in the Aegean sea.

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 swim stop is at Mesa Pigadia Beach or Red Beach. 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.

If you love the sea, if you seek to escape from the everyday routine, if you long for the intense emotions of nature, if you seek to broaden your horizons, then a catamaran sailing boat adventure is precisely what you want. Milos beauties are mostly hidden and unreachable by land. The catamaran will lead you to beautiful, pristine and isolated beaches, far from the hassle of the crowds. With this cruise, you will have the chance to discover most of the island coastlines and see the huge diversity of colours, caves and beaches Milos has to offer.

Milos is famed for its stunning volcanic coastlines, but the best views—and swimming spots—typically aren’t reachable by land. Spend the day out on the open water during this full-day private sailing cruise. Deluxe packages include lunch and drinks, plus get-down swimming or paddle-board stops at Kleftiko and Kalogries beaches.

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.

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.

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.

Spend the morning swimming, snorkelling and sunbathing on this 5-hour cruise from Santorini. Marvel at the volcanic landscapes at you cruise around the caldera, spot natural landmarks like The Indian and Nea Kameni island, and dive in to swim at Mesa Pigadia beach and Red beach. Along the way, cruise past Akrotiri lighthouse and Aspronisi island, take a dip in the volcanic hot springs, and tuck into a delicious BBQ lunch (included) on-board.

Santorini’s most dramatic beaches and volcanic coves are best reached by boat. This half-day catamaran cruise from Oia lets you explore the island’s coastline from the water, with stops for swimming and snorkeling along the way. Sail past scenic islands and beaches before settling in for a sunset meal—a BBQ dinner onboard, paired with local wine—as the caldera glows at dusk. Hotel pickup is included for added convenience.

Combine a visit to Santorini's caldera and hot springs with a trip out to the island of Thirasia with this cruise. You'll start at Nea Kameni, a volcanic island, where you'll have time to walk around the island and swim in its hot springs. You'll the cruise on to Thirasia, where you'll have enough time to have lunch and explore before sailing back to Santorini.

Reaching Mykonos’ hidden coves and neighboring islands can be tricky by land. This catamaran cruise lets you explore the Aegean from the water, with stops to swim and snorkel around Rhenia and historic Delos, or along the southern beaches of Mykonos. In between swims, relax on deck and enjoy a freshly prepared Greek meal served on board, with beer and wine included.