Top Cyclades Islands Sailing Tours

Most boat trips around Santorini are packed with people but this small-group cruise provides a more intimate sailing experience. Board your boat or catamaran and enjoy a relaxing day of swimming, snorkeling, and soaking up the warm Mediterranean sun. This excursion includes a delicious Greek barbecue lunch onboard paired with local wines and other refreshments.

Experience the joy of a full-day cruise to Delos and Rhania islands. Sail on a yacht in a small-group atmosphere, swim and snorkel in crystal clear waters, relax on beaches at the uninhabited Rhania Island, explore the ancient site of Delos Island, and savor a buffet of Greek delicacies. Lunch, all fees and taxes, beverages, and hotel pickup are all included.

Discover the wonders of Delos on a half-day tour from Mykonos, where ancient history comes alive. With an expert guide, uncover the fascinating stories behind the temples, sanctuaries, and artifacts, and explore hidden highlights that you might otherwise miss. This immersive experience ensures you leave with a deep appreciation of the island’s classical treasures.

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.

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.

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.

Admire a perspective of Santorini’s beaches, hot springs, and caldera that many visitors miss on this luxury or group catamaran cruise. Enjoy a stop to bathe in the warm springs of Palea Kameni, and snorkel or sightsee at the island's Red Beach. While aboard, sip local white wine and beer, and enjoy a delicious Greek meal prepared onboard. Finally, admire picture-perfect sunset views before the tour ends (if option selected).

Enjoy amazing moments in Milos island! An ideal cruise for you in order to see the most famous spots here in Milos such as Kleftiko the old famous pirate bay with the transparent waters! A short cruise that includes everything that you wish for your dreamy vacations. Swimming, snorkelling and for the end an amazing sunset!  You are free to explore the paradise!

Visit Volcano & Hot Springs by joining our most popular & low cost tour. An experience you don't want to miss! ideal for cruise travelers, as the boat tour begins at the port of disembarkation.

Santorini’s whitewashed houses and volcanic cliffs look their best from the water. Even if you only have a short time to spare, take in the views and discover the island’s geothermal wonders on this to-the-point trip by a traditional wooden caïque—from the same port that most cruise travelers arrive at. Visit Santorini Volcano and swim in the Santorini Hot Springs: Bring cash to pay the volcano entrance fee.

Some of Milos’ most beautiful spots can only be reached from the sea. Soak up the views in style on this small-group cruise by charming sailboat. Discover Kleftiko Beach’s sculptural formations, drop anchor at cliff-framed Gerakas beach, and swim in the turquoise waters of Poliegos, an uninhabited island. Your day includes breakfast, lunch, and drinks, including alcoholic beverages, for maximum comfort.

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.

If you’re seeking a luxurious way to see Santorini, look no further than this exclusive catamaran cruise—an extra-special way to explore one of Greece’s most picturesque islands. On a luxury sailing yacht, arguably the best mode of transport to explore Santorini, you’ll cruise to the Red Beach and stop at top swim and snorkel spots. Plus, unlimited alcoholic and soft drinks, hotel pickup and drop-off, and a Greek BBQ meal are included.

Santorini’s crowds can overwhelm during the busy summer season, so take a break from the throngs and marvel at the views of the coastline and surrounding islands with his private catamaran day cruise. Set sail from Ammoudi Bay and skirt Oia before crossing to Thirassia for a stop to swim. Continue on to Palea Kameni and Nea Kameni, dropping anchor to take a dip, snorkel, and enjoy a barbecue picnic on board before the return to port.

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.

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.

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 hidden gems of Santorini and cruise through the caldera, a must-do for any visit to the island. This morning or sunset cruise is operated by catamaran, offering a faster and more stable ride. Spend your time sipping on local wines and beer, indulge in a seafood and barbecue dinner, swim and snorkel in crystal-clear waters, and take a dip in the hot springs. The afternoon cruise ends with a famous Santorini sunset.

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.

Sail the sea near Santorini in style aboard your own private catamaran, on this relaxing excursion with 2-way hotel transfers. Spend the day swimming, snorkeling, and sunbathing amidst this Greek island’s most secluded beaches. You’ll also get to marvel at Santorini’s unique rock formations, swim in undersea hot springs, and enjoy a barbecue meal with wine, beer, and soft drinks. Choose between daytime and sunset cruises.

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.

Explore Santorini in style with this private sailing charter. You'll start with a visit to Red Beach for swimming and snorkeling before heading to the picturesque White Beach. Sail past the 19th-century Akrotiri Lighthouse without stopping, then swim and snorkel at the Nea Kameni Hot Springs in the caldera. The trip concludes with more snorkeling and swimming off Thirassia island. Hotel pickup and drop-off are included for your convenience.

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).

Discover a new perspective on the beaches, bays, and islands around Santorini—and enjoy a more personal sightseeing experience—on this small-group, half-day catamaran cruise. Jump offboard to swim and snorkel at the Red and White Beaches; take a dip in the volcanic hot springs; and tuck into a delicious BBQ lunch on-board. Pick between morning and afternoon departure times hotel pickup and drop-off is also included for your convenience.