Top Cyclades Islands Sailing Tours - page 3

This daytime cruise provides a stress-free overview of Santorini’s natural and historic beauty, making it ideal for first-time visitors and travelers with limited time. Hop on the bus at the meeting point in your village, then join your traditional Greek caïque boat for a caldera cruise. You’ll scale Santorini Volcano (entrance at your own expense), swim in the Santorini Hot Springs, and enjoy free time on charismatic Thirasia island.

Join this group catamaran cruise that goes to both Milos and Poliegos, plus serves up a homemade menu with barbeque and drinks. You don’t need to organize anything. Just show up ready to swim in turquoise water, snorkel, hang out on the beaches, and maybe swim in natural hot springs. You can also check out a traditional fishing village, Kilma.

Skip the ferries and crowded tourist beaches; take a luxury catamaran out into the Aegean Sea instead. On this small-group cruise, sail along the picturesque south coast of Mykonos or set out for Delos, a UNESCO World Heritage Site and home to a large range of ruins, sculptures, and ancient mosaics. Spend most of the day relaxing on your own terms: swim, snorkel, sunbathe on the beach or explore the sites without anyone to rush you through it.

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.

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!

Enjoy a full day out on the open water during this small-group sailing excursion from Paros to Naxos. Dig into a tasty onboard lunch with alcoholic drinks 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.

Milos is renowned for its stunning Aegean coastlines, but many of the island’s most spectacular sights are only reachable from the water. Spend the day out on the open sea during this full-day small-group sailing and snorkeling excursion, covering Milos’ western side. Tours include five get-down stops, from the volcanic sands of Kleftiko Beach to the bay of Agios Dimitrios. Top it off with Breakfast, alcoholic drinks, and a traditional Greek lunch.

Enjoy a relaxing day cruising in a catamaran along the southern coast of Mykonos and to beautiful Rhenia Island. Visit places that would take much longer to get to independently. Spending the half-day cruise admiring the views, lounging on the sundeck, swimming, snorkeling, stand-up paddle-boarding, and kayaking. A delicious 3-course meal will be served on board, and the catamaran is even equipped with indoor showers so you can freshen up.

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.

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.

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.

Spend the morning swimming, snorkelling and sunbathing around Santorini on this 5-hour cruise. Along the way, see landmarks such as Indian Head Mountain and the Old Venetian Lighthouse; visit the Red and White Beaches; and take a dip in the Hot Springs. Tour includes hotel pickup and a delicious BBQ lunch on-board.

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.

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.

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.

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.

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.

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.

Get views of Santorini from aboard a catamaran during this boat excursion. Sip unlimited beer, wine, and soft drinks while taking in glimpses of the island's beaches and volcanic landscape. Make stops at the White Beach, soak in some local hot springs, go snorkeling, and watch the sun dip below the horizon in Oia. Barbecue meal and hotel pickup and drop-off included.

Santorini’s sunsets are famous the world over, and there’s few more indulgent ways to see one than from your own private sailing yacht. This 44-foot (13-meter) yacht has space for up to 10 travelers, while the friendly crew will provide not only free-flow beer, wine, water, and soft drinks, but a full dinner. See Red Beach, White Beach, and Palea Kameni before anchoring at Thirassia Island for your sunset feast.

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.

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.

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.

Take a break from the beach with this cruise around Santorini's volcanic islands. Sailing from spot to spot on a traditional Greek caïque boat, explore the volcano at Nea Kameni (entrance at own expense); relax in the sulfur hot springs off Palea Kameni; and enjoy free time to explore Thirasia. After your cruise, transfer to the village Oia to watch an Aegean sunset from Santorini’s cliff edge.