Top Cyclades Islands Sailing Tours

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.

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.

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.

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.

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 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.

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!

Experience the best of Paros on a half-day boat tour to two of the island’s most breathtaking and unique locations! Swim and explore the mysterious Pirate’s Cave with its dramatic cliffs and legends, and unwind in the crystal blue waters of the Blue Lagoon. This unforgettable family friendly journey blends adventure, relaxation, and stunning natural landscapes. Designed for explorers, sea lovers, and those chasing the extraordinary – this tour is the ultimate island escape. Reserve your spot and let the Aegean work its magic! I

Enjoy the classic tour trusted by thousands of visitors to Santorini for decades. Ideal for cruise travelers, as the boat tour begins at the port of disembarkation. Relax on a wooden traditional Greek boat and visit the active volcano of Santorini, a unique geological park built of lava. Swim in the mud baths created by the many volcanic eruptions. visit traditional Thirassia that will take you back in time 30-40 years and swim in its deep blue waters. Returning you can take pictures from the unique landscape of the village of Oia with its white houses and blue domes from the boat. Is a value for money trip aimed at visitors and families who want to enjoy nature and landscapes and avoid the hustle and bustle of the city. Post unique landscapes and the crystal clear waters of the Caldera.

Experience one of the best Milos boat tours with a sailing cruise to Kleftiko along the island’s stunning west coast. Departing from Adamas, sail past volcanic landscapes, hidden coves and sea caves, with multiple stops for swimming and snorkeling in crystal-clear waters. Visit Kleftiko, swim at Kalogries Beach and explore Sykia Cave, some of Milos’ most iconic locations. Relax on deck and enjoy breakfast, lunch, drinks, seasonal fruits and traditional sweets served on board. With a small-group setting and experienced local crew, this sailing cruise offers a comfortable and unforgettable way to discover Milos. Highlights Full-day experience (10:00–17:00) Visit Kleftiko, Sykia Cave & Kalogries Beach Swimming, snorkeling and cave exploration Breakfast, lunch, drinks, fruits & sweets included Small-group experience with local crew Important Note: The itinerary is indicative and may be adjusted depending on weather, sea conditions, or for the safe operation of the cruise.

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.

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.

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.

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.

Take a break from the resort crowds and get offshore for a while on this chilled-out sailing excursion around Mykonos. Choose a trip to the beaches on the south coast of this idyllic island or head west to the Delos, an important island in Greek antiquity with plenty of ruins to explore. Either way, whether you’re swimming, snorkeling or discovering sites from Greek mythology, what you do is entirely up to you – there are no rigid schedules on this cruise.

Sail through the Greek water with the wind on your face on this small-group tour to delos and Rhenia Islands. You can help sail if you like, or leave it up to your crew. Your skipper will take care of all the logistics, so you can relax, swim, sip on a glass of wine, and enjoy your provided lunch on your sailboat.

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.

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.

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.

The opportunity to see all South beaches, soak up the sun, snorkel to crystal clear waters, and meet new people. The opportunity to explore the Aegean beauty. The opportunity to taste Mediterranean food and drink Greek wine. The uniqueness of the tour refers also to the professionalism of the captain and the crew, their smile, and their willingness to help you enjoy unforgettable moments on the island of the winds.

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.

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.