Top Cyclades Islands Sailing Tours

Combine a visit to Santorini's caldera and hot springs with a trip out to the island of Thirasia with this cruise. You'll start at Nea Kameni, a volcanic island, where you'll have time to walk around the island and swim in its hot springs. You'll the cruise on to Thirasia, where you'll have enough time to have lunch and explore before sailing back to Santorini.

Get off Santorini’s main island and explore the volcanic islets around it, which are home to unique volcanic landscapes. Visit two islets accessible only by boat. Sail to Nea Kameni to hike up to the crater of the active volcano (own expense) and to Palea Kameni, where you can soak in naturally-heated pools.

Experience the volcanic beauty of the Aegean and an unforgettable Santorini sunset on this afternoon catamaran cruise. Travel in style and comfort aboard a luxury catamaran, stopping to bask on Santorini’s red and white sand beaches, snorkel among crystalline waters, and soak in volcanic hot springs. With included hotel transport plus a fresh Greek barbecue and unlimited soft drinks, beer, and local wine served onboard, it's a decadent way to enjoy the island’s famous sights.

Escape the crowds on land and admire Mykonos from the water on a luxury catamaran cruise that takes you off the beaten path to Rhenia, an uninhabited island surrounded by crystalline waters and home to ancient Greek ruins. You’ll have free time to spend as you please, either exploring the island, swimming, or soaking up the sun—you choose. Itinerary is subject to weather conditions and might be adjusted to ensure safe cruising of passengers. The alternative route normally visits the famous Mykonian southern coast instead of Rhenia.

Escape busy Mykonos for a day—and discover two of the region’s highlight islands—on this paradisiacal sailing tour. Following morning departure, head to Rhenia Island to swim, sunbathe, and explore the scenery at leisure. After a traditional Greek barbecue lunch on board, continue to Delos Island, said to be Apollo’s birthplace. Depending on your interests, visit its archaeological site (entry own expense) or the island’s tranquil beaches.

Indulge in the ultimate day of fun in the sun on this all-inclusive, 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.

Go on a half-day 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, dinner, wine, and hotel pickup and drop-off included in the tour price.     

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.

Make the most out of your time in Santorini aboard this relaxing and tranquil sunset sail on a catamaran. Enjoy the splendid views from the catamaran as it sails around Santorini. Swim and snorkel in the blue sea and indulge in a delicious barbecue dinner prepared onboard. Imbibe unlimited drinks such as local wine and water.

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.

Set sail on the bright blue Aegean with this unforgettable catamaran cruise from Mykonos. Swim and snorkel in the crystalline coves around the islands of Rheina and mythical Delos, or visit the pristine southern beaches of Mykonos. Drop anchor for a delicious, multicourse Greek meal cooked up right on board, accompanied by unlimited beer and wine from an open bar.

Santorini Volcano sits on its own islet some way off the coast of Santorini. There are no water taxis or ferries, so a tour is the only way to visit, and tickets often sell out far in advance. Don’t miss your chance to sail into the caldera, swim in the undersea hot springs, walk along the volcano ridge, and discover the volcano’s history and geology: Entry is at your expense.

Experience Santorini’s scenery, hot springs, and beaches on a cruise with onboard dinner and glass of wine included. After pickup from your hotel, settle onto your cruise boat, and sail around the caldera and island’s shores. Along the way, bathe in the Nea Kamini hot springs; explore the beaches; and savor a delicious 2-course Greek dinner while floating on the water as the sun sets.

Explore Santorini’s stunning caldera on this cruise with pickup from the Port of Athinios. You’ll see the  active crater on the lava island Nea Kameni and dip your feet in the hot springs of Palea Kameni. On Thirassia, you’ll have free time to swim at the beach, have a waterside lunch at your own expense, or simply explore the Village of Manolas.

Visit the surrounding islands of Santorini aboard a morning cruise. Head to Nea Kameni to see a volcanic crater, swim in the warm waters of the lava island of Palea Kameni, and enjoy some free time to explore Thirasia—which was once part of Santorini. Your final stop of the day is the beautiful village of Oia, where you can enjoy stunning views of the surrounding area from the castle.

Explore the Aegean island of Milos on this sailing excursion. Enjoy a small group experience that includes visits to Cape Vani, Kalogries Beach, and Agios Dimitrios bay. Check out the caves of Kleftiko and Sykia by dinghy, go swimming and snorkeling, and relax by the sea. Enjoy complimentary lunch, snacks, drinks, access to snorkeling equipment, and GoPro photos.

Ride the ferry from Mykonos to Delos with a local guide who shares expert knowledge about the UNESCO World Heritage–listed island. Unveil the drama of Delos during this half-day walking tour through the excavated ruins of its main archaeological site. See the Terrace of the Lions, House of Dionysus, Archaeological Museum of Delos and more as you learn about the sacred isle’s place in Ancient Greek history. Meet at the port or upgrade to include pickup from Mykonos hotels.

Cruise around Santorini on this half-day catamaran tour departing from Vlihada Marina. Observe famed sights such as the Venetian Lighthouse, the Indian Rocks, the Red Beach and the White Beach as you glide atop clear blue water. Enjoy a swimming and snorkeling excursion, then take in panoramic views of the Aegean Sea and the small neighboring Cyclades Islands during the return trip. During the trip indulge in a buffet-style BBQ meal and sip drinks from the open bar on board.

Experience some of the top attractions around Santorini on this boating adventure. After a convenient hotel pickup, enjoy activities that include sailing across Santorini’s caldera to Palea Kameni and Thirasia, marveling at Santorini’s scenic beauty on the way to Nea Kameni, relaxing in thermal pools, and upgrading for a sunset excursion in Oia.

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.

Take a cruise out to the caldera of Santorini aboard a catamaran and spend some time checking out the island's colorful beaches with this tour. You'll have time to swim at Red Beach and soak in the hot springs at the caldera of Santorini, with time left over for swimming and an included lunch or dinner at Mesa Pigadia Beach.

Cruise the waters off Santorini during this 5-hour boat journey. Step aboard the luxury catamaran and relax in one of the comfortable seating areas as you sail out of Amoudi port. Stop first at the volcano to take a dip in the hot springs or indulge in a mudbath. Sail past one of the oldest lighthouses in Greece, Akrotiri, then go to the Red and White beaches area. Swim, relax and enjoy a traditional Greek barbecue meal. Food, snorkeling equipment, open bar and round-trip hotel transportation are provided. This Viator exclusive tour is not available anywhere else. 

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.