Top Cyclades Islands Sailing Tours

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.

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.

The Little Italy area of Mykonos can get crowded, but this Mykonos Sunset Cruise with Drinks from Tourlos takes you on the water, away from the tourists on land. Cruise the water and enjoy drinks and snacks as you take in views of the area. Your boat drops anchor right at sunset so you can fully enjoy the picturesque views of the setting sun over the ocean.

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.

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.

Our luxury catamaran combines space and style, crafted to offer you complete comfort. Whether you stretch out on a sunbed, unwind in a shaded lounge, or dance under the open sky, you'll always find your perfect spot. Soft, uplifting music sets a warm and joyful tone throughout the day. Between smiles and melodies, you'll enjoy Greek snacks, a light brunch, and a delicious lunch — all included. Espresso, tea, water, soft drinks, local Greek white wine and beer are available whenever you wish. For those seeking adventure, the sea becomes your playground. Try stand-up paddleboarding, explore underwater life with snorkeling gear, or simply drift on an inflatable noodle. And of course, our iconic pink flamingo float is always ready for your next unforgettable photo. Whether you're after excitement or gentle relaxation, there's something for everyone.

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.

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.

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.

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 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.

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.

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.

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.

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.

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

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.

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.

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.

Watch one of Santorini’s famous sunsets from aboard a sightseeing boat with this cruise expedition. You’ll visit the caldera and its hot springs before sailing on to the island of Thirasia, where you’ll have some free time to explore. Enjoy a detailed dinner including chicken fillet, mixed meatballs, greek salad, grilled vegetables, and wine as you sail back to Santorini.

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.

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.

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.