Top Cyclades Islands Sailing

Sail to the most unknown corners of stunning Cyclades Islands such as Kea, Kythnos, Syros and Serifos and walk in the footsteps of the ancients along beautiful trails, in this small group week-long sailing holiday. Choose one of the available departures and sail on top of the range boats which are navigated by qualified skippers eager to share their regional knowledge with you. Whether you’re an experienced sea and land adventurer or it’s your first time, you’ll enjoy a unique, multi-level experience in the Aegean Sea. Connect with like-minded travelers and learn the basics of sailing or simply kick back to bask in the sun whilst enjoying the caresses of the Aegean winds.

Sailing across the coastline, leaving behind us Milos bay, we will pass by the traditional fishing villages of Skinopi, Klima, Areti and Fourkovouni with the colourful little houses - called "Sirmata"- built by the sea side. Then, we will visit Arkoudes, a complex of lava rocks, which takes its name by its characteristic shape, a bear. Opening the sails, we are heading to the impressive Cape Vani and our first stop for swimming, the natural bay of Kalogries, ideal for diving from the catamaran in its transparent waters. Follows the stunning cave of Sikia, where we will enjoy the view and you will be able to see the characteristic hole in its roof as well as the entrance of the cave.

Our meeting point is at Adamas port at 10:00 a.m, where a van will be waiting to take you to Pollonia and start our cruise. If you are staying at Pollonia, you can join us directly at the dock at 10:15 a.m. After the cruise, we will disembark at Adamas and bring you back by van to Adamas. Leaving Pollonia at 10:30 a.m, we will sail towards Poliegos island, passing by the islands of Kimolos and Agios Eustathios. Our first stop for swimming will be the amazing bay of Galazia Nera, in Poliegos! There, the geological formations created a perfect setting for a lagoon, where the waters are extra transparent and even bluer than in any other place around Milos. You will have time to swim in this paradise and a nice snack will be waiting for you back on the boat.

Naxos, Iraklia & Schinousa on a sailing boat

Round of Antiparos & Despotiko on Athanasia sailing boat

Full Day Mini Cruise Mykonos "South Beaches" ORNOS, DRAGONISSI, FRANGIAS, PARADISE, TROPICANA BAR & KALAFATIS 9-hour excursion with guaranteed departures from 2 May to 31 October, every Monday, Wednesday and Saturday morning. Included in this excursion: • Sea transportation in a classic Greek boat. • Sailing to the most beautiful beaches in the south of the island, including "Paradise". • Picnic with snacks and the typical Greek aperitif "Ouzo". • Lunch with limited drinks.

Experience the Cyclades’ natural beauty and history on this luxury cruise to Rhenia and Delos islands. After a convenient hotel pickup, board a 112-foot (34-meter) yacht and sail for the picturesque, uninhabited island of Rhenia. Go snorkeling with complimentary gear and enjoy a delicious lunch with wine and beer—they’re included in the tour—before heading to the sacred ruins of Delos for a guided tour.

An off-the beaten-track experience enjoying a quick sailing ride along the coast of Mykonos. Take your on-board “Aperitivo” with drink of your choice and local Greek snacks while the sun drowns in the Aegean Sea. A cruise for adults only where you can discover, wearing your casual look, the real and natural beauties of the Island on sunset time.

Set the sails to the wind and explore the exclusive beauties of Mykonos on a sailing yacht with the onboard buffet of Greek flavors and complimentary wine, beers, and soft drinks. Enjoy a beach safari to the most beautiful and famous south-coast beaches. Relax and swim in a secluded bay of Rhenia Island. While sailing, see the archaeological site of Delos from the water.

Discover the beautiful Cyclades Islands the way they were meant to be seen—from the water! On this full-day yacht cruise from Mykonos, sail across the turquoise Aegean to the uninhabited islands of Rhenia and Delos, stopping to swim and snorkel at a pristine beach cove. Customize your day at sea with either a guided visit to the UNESCO-listed archaeological site at Delos or an extra swimming stop, and savor the good life with a light Greek lunch and refreshing drinks onboard.

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. 

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.

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.

If you’re seeking a luxurious way to see Santorini then look no further than this Viator 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 on, you’ll cruise to 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.

Cruise Santorini’s gorgeous coast aboard a sailing catamaran, enjoying the luxury and exclusivity of a private yacht as you swim, take mud baths, and use the boat’s snorkeling gear. With a captain and crew to tailor the experience to your group of up to 15 people, you’ll also enjoy a meal of fresh-grilled meat and vegetables, seafood, and traditional Mediterranean dishes that’s perfect for feasting on deck.

Explore the beaches, bays, and islands around Santorini on this catamaran cruise. Along the way, jump off 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. Hotel pickup and drop-off is included.

Santorini’s sandy beaches and glittering waters make an idyllic backdrop for a sailing adventure, but sharing a boat with dozens of other tourists can detract from the experience. This private 5-hour cruise is tailor-made for you, so you can enjoy swimming and snorkelling, soak in the hot springs, and admire landmarks such as Indian Rock and Akrotiri. A barbecue lunch and unlimited drinks are served on-board.

Spend the day sailing around beautiful Santorini on a catamaran. Imbibe unlimited amounts of white wine, soft drinks, and water and indulge in a delicious barbecue prepared onboard the catamaran as you sail in the gorgeous blue waters of the sea off the shore of Santorini.

Take to the Santorini seas for fishing, swimming and snorkeling in hidden bays and one-of-a-kind fishing destinations. Leave the crowds behind and enjoy the tranquility of these secluded spots on this private boat tour. Explore the Santorini coast and the Aegean Sea, and sail around the grand Nea Kameni volcano, with your own boat captain. Personalize your schedule based on what you want to do, whether you want to take photos of the island landscapes or simply catch the big one.

Our sailing trip from Paros leaves from Piso Livadi every day taking you sailing for a full day in an exclusive itinerary around the Small Cyclades island complex, weather permitting. As we leave Paros behind, we are heading towards the island of Irakleia, where a stop in a secluded cove will give you the change to snorkel around a WW2 wrecked plane. Schoinousa or Koufonissia are planned for our next stop, where after a swim in the turquoise colored waters you’ll be served lunch prepared by our crew. Later in the afternoon, a short swim stop off Naxos (southern coasts), where our final stop is. As an alternative route, when winds make crossing to Naxos tough, we set sail westward towards the sheltered coasts of Antiparos & Despotiko, which are some hidden gems around the Cyclades waiting to be explored. Our return is scheduled between 19:00-19:30, as sometimes weather dictates the speed and course.

Enjoy a romantic sunset sail in the Aegean Sea on this half-day pirate ship adventure from Ios. Board a classic wooden vessel at the island’s port and explore gorgeous bays, experience spectacular views, and sip a delicious signature cocktail prepared by the crew and included in the tour price. Return to port just in time to hit the island’s nightlife scene.   

Your crew will welcome you aboard your yacht the first day and, in the afternoon, we set sails for a unique 7day itinerary, taking you around the highlights of the Saronic gulf. Our daily schedule starts with a rich Greek breakfast onboard. We set morning sails heading picturable quite bays for swimming, drinks and snacks. Lunch with Mediterranean dishes, local specialties and wine is served on board. Afternoon sailing heading our next port. Free time to explore a new destination each day and spend the evenings your way. By the end of the trip, we aim to have offered an introduction to sailing and Yachting life, a unique way of holidaying, along with high-standard authentic Greek hospitality.

We chose a modern Catamaran with an experienced crew to sail you around the islands of this route, such as the less known Antiparos, Schoinoussa & Koufonissi, along with the larger and more famous islands of Naxos and Mykonos. Our sailing yacht may comfortably accommodate up to 8 guests, in 4 double bed cabins all with en-suite facilities and Air-Conditioned. Our daily schedule includes most of the days 2 swim stops, in the morning and another at around noon time, when lunch will be served and our schedule includes arriving early afternoon in each port, so you will have time to explore each destination. Our meals on board, include fresh seasonal ingredients bought & prepared on each day, and will give you an insight into a home-made Greek meal different each day. By the end of the trip, we aim to have offered an introduction to “yachtlife”, a totally different concept of holidaying, the exploration of our country from the sea, and of course high-standard authentic Greek hospitality.

Go on a half-day Sunset sailing adventure in the Aegean Sea. Visit the Mythical island of Delos. Relax at the beach, snorkel in the beautiful turquoise water. Enjoy lunch, dinner, wine, and hotel pickup and drop-off included in the tour price. - Sail and explore the islands of Rhenia and Delos. - Enjoy flexible departure times to suit your travel schedule and interests. - Kick back at picturesque Aegean beaches and check out Apollo’s birthplace - Make the most of limited time with convenient hotel pickup and drop-off.