Top Cyclades Islands Sailing Tours - page 3

Sailing around the Aegean Sea doesn’t have to break the bank. Instead of arranging a costly private charter, explore both the coastlines of Milos and the uninhabited island of Poliegos during this cost-effective, small-group excursion. Spend the day swimming, snorkeling, or paddle-boarding in secluded bays and caves—or simply relax on the crew-staffed boat with a drink in hand.

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.

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, protein shake, 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.

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.

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.

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.

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.

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 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.

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.

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, 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.

Explore the stunning volcanic coastline of Milos—and enjoy three swim stops plus a stop in Kleftiko—during this full-day sailing excursion. Enjoy close-up views of Milos' attractions, from the colorful fishing village of Klima to the rock formations of Cape Vani. Other highlights include a swim and snorkel stop at the ancient pirate hideout of Kleftiko, and swimming at Kalogries Beach and Agios Dimitrios.

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.

See the highlights of Santorini from the water's edge on this luxurious, half-day catamaran tour. Pick from morning or afternoon tour times and, following hotel pickup, you’ll be transferred to the port. Once aboard, set sail on a sightseeing tour, and see highlights including the Red Beach, White Beach, Santorini’s caldera, and more. This private tour also includes multiple swimming stops, a full meal on board, and unlimited drinks.

Enjoy a full day on the open water during this small-group sailing excursion from Paros to Naxos. Dig into a tasty onboard lunch with snacks and limited wine and beer included. Highlights include a snorkeling stop at a WWII-era wreck and multiple swimming stops in Schoinousa, Koufonissia, and coastal Naxos, depending on weather conditions.

Set sail aboard one of the most luxurious vessels in Santorini, the one-of-a-kind Ipanema 58 catamaran. On this tour, feel like a member of the jet-set as you cruise inside the caldera for a soak in volcanic hot springs, swim and snorkel at the island’s Red and White Beaches, and watch a famous Santorini sunset from the water (if later time selected). Relax on spacious deck lounges and be pampered by an attentive crew, who serve up a delicious Greek barbecue lunch.

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.

A peaceful romantic trip with the essence of a cruise to be unforgettable. Embark on this afternoon excursion!

Set the sails to the wind and explore the islands of Delos and Rhenia on a sailing yacht with the onboard buffet of Greek flavors and complimentary wine, beers, and soft drinks. Relax and swim in a secluded bay of Rhenia Island. We sail back to Mykonos, watching the breathtaking landscape of yellow, orange, and red colours as the sun goes down over the very blue Aegean Sea.

Experience Milos’ south coast and the white cliffs and coves of Kleftiko in style on this surprisingly affordable private sailboat charter, with a tender to get you right into the caves and shower and restroom too. Good for up to eight travelers, your package includes snacks, water, soft drinks and a bottle of wine, with a high-quality Bluetooth sound system for your favorite tracks: be sure to enable roaming.

Skip the crowded beaches and enjoy a leisurely private cruise along Santorini’s stunning rocky coastline. Private tours include a swimming stop off the coast of Nea Kameni—a tiny volcanic island that most visitors miss—and another swimming or snorkeling stop by Thirassia. Snorkeling equipment will be provided and tours end with a sampling of traditional Greek refreshments.

Step aboard our catamaran with Santorini Yachting Cruises, and join us for an incredible sailing adventure! Our Santorini day cruise sets sail from the picturesque port of Vlychada, weaving through the Aegean Sea with a first glimpse of the striking Red Beach, setting the stage for an exhilarating swim. As we navigate past the White Beach, the Indian Rocks and the iconic Venetian Lighthouse, our Sailing voyage unfolds. The highlight of our journey awaits as we enter the awe-inspiring Caldera, leading us to a stop at the renowned Hot Springs of the volcano for a rejuvenating swim. We conclude our adventure with a stop at Mesa Pigadia Beach in the island's southern reaches, where you can relish a delightful break for swimming and a traditional Greek lunch & drinks on the Catamaran. We then set sail back to Vlychada, offering you the perfect opportunity to capture the breath-taking beauty of the Caldera, enhancing the conclusion of your sailing journey with the best views of Santorini.

Take to the Santorini seas for fishing, swimming and snorkeling on this one-of-a-kind, private tour. Leave the crowds behind and enjoy the tranquility of these secluded spots. Explore the Santorini coast and the Aegean Sea, and sail around the grand Nea Kameni volcano, with your own captain. Personalize your schedule based on what you want to do—and do your best to make a big catch.

Make the most of your time in Santorini with a private yacht charter for exploring around the island. You can choose a morning or afternoon half-day tour, and you can coordinate your trip to enjoy the sunset if you like. Admire the views as you dine on a tasty Greek meal on board, and swim and snorkel in the clear seas in sheltered coves.