Top Cyclades Islands Sailing Tours

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.

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.

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.

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

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.

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.

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.

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.

Our semi-private Mykonos sunset cruise offers the perfect blend of luxury, relaxation, and breathtaking scenery. Sail along the island’s famous southern coast, passing iconic beaches like Psarou and Super Paradise, while enjoying refreshing swims in crystal-clear waters. Onboard, indulge in a freshly prepared Greek ΒΒQ meal, featuring delicacies, salad, and authentic local flavors, paired with refreshing drinks. As the sun begins to set, experience the magic of the Aegean sky transforming into shades of gold, pink, and purple, creating a truly unforgettable moment. With a premium catamaran, expert crew, and intimate atmosphere, this is more than just a boat tour, it’s a once-in-a-lifetime Mykonos sunset experience. Book now and let the Aegean’s beauty take your breath away! *Route may be adjusted by the captain based on weather conditions to ensure safety and comfort. This cruise operates using a fleet of two or more premium catamarans.

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.

Escape the summer heat and crowds on Santorini and explore the coastline and nearby islands with this small-group catamaran day cruise. Set sail from Vlychada Marina and skirt Red Beach before stopping to take a dip at Mesa Pigadia Beach. Continue on to Palea Kameni and Nea Kameni, where you’ll have time to swim, snorkel, and relax with a barbecue lunch on board before the return to port.

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 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.

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.

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.

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.

Enjoy a relaxed way to sightsee in Santorini, all thanks to this luxurious, half-day catamaran cruise. Upon departing from Vlychada, look forward to discovering the Red Beach, White Beach, Akrotiri Lighthouse, and other sightseeing highlights from the water’s edge. Along the way, make multiple stops for swimming and snorkeling—and enjoy a generous buffet lunch and drinks on board.

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.

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.

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.

Enjoy a night to remember in Santorini—and experience many of the island’s highlight attractions in just one excursion—on this luxurious sunset catamaran tour. Setting off from Vlychada, get ready to discover the Red Beach and Santorini’s volcanic caldera, and admire the sunset. In between, savor a traditional Greek meal complete with local wine, plus time to swim and snorkel at your own pace.

Enjoy a half-day cruise and discover the most beautiful places in Milos sailing on the West and South side of the island, exploring the caves of the famous old pirate bay of Kleftiko and discovering a part of the South side.