Top Cyclades Islands Sailing Tours - page 2

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.

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.

That semi private sailing tour is a family friendly sunset tour, due its small number of maximum participants and allows you to enjoy The idyllic Parikia Sunset under relaxing music , while swimming as you passing through some of nicest sea locations. Our experienced captain will choose the most protected areas from winds and occasionally might change the route of trip, in order to be more enjoyable- as safety comes first . She is so polite and ready to provide details about passing through locations or sea stops. Snorkelling equipment is available and swimming allowed in all sea stops. Prepare your camera and get ready to fall in love one more time!! A minimum participation of 4 people is required; otherwise, the activity may be cancelled.

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.

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.

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.

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.

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!

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.

Staring from Piso Livadi port, located at the South East coast of Paros we offer a half day sailing cruise, tailored for the traveller who wants to get the maximum of his stay on Paros. Choose a cruise in the morning or afternoon (with sunset atmosphere) Highlights are the famous BLUE LAGOON and the sea caves of Tripiti. Greek dishes are served to enjoy mediterranean flavors and complete your experience

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.

Sailing across the coastline, we will pass by the traditional fishing villages of Skinopi, Klima with the colorful little houses – called “Sirmata”- built by the seaside, Areti and Fourkovouni.

Then, we will visit Arkoudes, a complex of lava rocks, which takes its name from its characteristic shape, of a bear. 

Opening the sails, we are heading to the impressive Cape Vani and our first stop for a swim, the natural bay of Kalogries. Follows the stunning cave of Sikia, where we will be able to see the characteristic hole in its roof as well as the entrance of the cave. 
 The famous old pirate bay of Kleftiko is the next stop, where our crew will guide you to explore it ! 

Next will visit beach of Gerakas and its hot springs. 
 Then we will head to the largest uninhabited island of the Cyclades, Polyaigos. There we will swim in the "Blue Waters", an area with amazing turquoise waters. 
Last stop for photography is Glaronisia (three volcanic islands).

Experience Milos’ south coast and the white cliffs and coves of Kleftiko in style on this surprisingly affordable private sailboat charter. Enjoy unlimited bottled water, soft drinks including Coca-Cola and Fanta, a bottle of chilled white wine, and snacks, with a tender to get you right into the caves and shower and restroom on board. Good for up to eight travelers, with a high-quality Bluetooth sound system for your favorite tracks.

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.

Enjoy a bucket-list-worthy experience on this half-day Santorini sailing tour. Step aboard the luxury catamaran and relax in one of the comfortable seating areas. Stop to take a dip in the island's hot springs, sail past one of the oldest lighthouses in Greece, and visit the Red and White beaches. Swim, relax and enjoy a traditional Greek barbecue on board. Snorkeling equipment, an open bar, and round-trip hotel transportation are all included.

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.

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.

Experience the magic of Milos on a luxury catamaran cruise designed for total comfort and adventure. Your journey begins at Adamantas, sailing first to the otherworldly lunar landscape of Sarakiniko for breathtaking photos of its famous white rocks. Next, dive into the electric blue waters of Galazia Nera on Polyegos Island, a hidden paradise known for its striking turquoise color. We continue to the tranquil Spathi Beach for a relaxing swim and a freshly prepared Greek lunch featuring organic, local ingredients. Afterwards, we reach the legendary Kleftiko, a former pirate hideout with towering cliffs and sea caves. Here, the sea becomes your playground – enjoy snorkeling, stand-up paddleboarding, or relaxing on our iconic pink flamingo. The return journey is equally spectacular. Capture photos of the majestic Sykia Cave and dramatic Cape Vani before sailing past the colorful "syrmata" boat garages of Klima village. With an open bar, professional crew, and elegant atmosphere.

Leave the crowds on Mykonos behind and catch the wind with this sailing cruise to two nearby Aegean islands. Set sail from Tourlos Bay to the UNESCO-listed island of Delos to explore the ancient Greek ruins at your own pace. Then head to the island of Rhenia, with a stop to swim and snorkel in the crystalline waters. Relax over lunch on board, served with wine, beer, and soft drinks.

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

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.

With its volcanic origins, dramatic scenery, and turquoise waters, Milos is one of Greece’s most spectacular islands—and this full-day yacht tour offers the perfect way to discover its highlights. Hop aboard your vessel at Adamas, and set sail. Admire colorful rock formations, visit numerous beaches (including Kleftiko Beach), enjoy meals and beverages, have free time to swim and snorkel, explore Poliegos Island, and more.

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.

Many Santorini sailing tours can be overcrowded—but this small-group excursion offers a more personal way to explore the island. Set sail on the Aegean Sea from Vlychada Marina, and look out for key sights from the Red Beach and Palea Kameni to the Akrotiri Lighthouse. Along the way, drop anchor to swim and snorkel in the clear water, enjoy a freshly prepared meal, and admire the sunset over the caldera.