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Unforgettable sailing vacations - mooring in hidden bay
Cyclades sailing trips - itineraries and maps

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Cyclades Sailing

Going on a Cyclades sailing trip is a lifetime adventure, that is sure to make you want to come back. Let us show you the wondrous, hidden bays with their crystal clear turquoise waters, hike the local footpaths with their unmatched views, marvel at the remnants of ancient civilizations dating as far back as 3000 B.C., experience the strong proud culture of modern day Greece, and let us tantalize your senses with the smells and tastes of the simple, yet wholly satisfying Greek cuisine.

Our skipper and host will keep you physically active (swimming, hiking, cycling, sailing), engaged, informed, and oh so relaxed the entire trip. Select your ideal package from our Greece sailing trips page.

You will experience the best of what the Cyclades have to offer. Each Cyclades sailing trip is slightly unique because sailing depends on the weather. Our knowledgeable skipper will work with the passenger group to choose the most suitable and fulfilling itinerary for everyone.

These are some of the islands the winds will take you to.


Amorgos: This stunning island has so much to offer that you will need a full day to hike its many scenic, ancient footpaths, and explore one of the most picturesque towns in all of the Cyclades with its maze-like narrow streets, 13th century church, monastery, and squares. You will explore its top attraction, the Monastery of the Virgin Mary (Panayia) Hozoviótissa, which is a 10th century cliffside monastery.  You cannot leave this island before you splash around its magnificent beaches, discover its caves, and gaze through its crystal clear aquarium-like waters.


Donousa: Explore this abundantly vegetated island’s wonders from the land and the sea. Donousa invites you to take its many local foot trails from town to town and when the heat gets too much, explore its natural caves and secluded beaches that are only accessible by sea. There is even a wreckage of a German WWII ship that’s yours to discover.


Folegandros: Dive into Folegandros’s gorgeous beaches and in the evening explore the traditional unadulterated Cycladic architecture and delicious cuisine of Hóra.


Ios: Explore the labyrinth of footpaths of the traditional hilltop old town and either as a group or on your own, discover the secluded beaches of Ios.  In the evening, enjoy as much or as little of the nightlife that breaks loose after dark.


Iraklia: Compare Saint John’s huge cave to Cyclops’s cave on this quiet island with emerald-colored water beaches, many footpaths, a cape that shelters wild sea birds, and WWII underwater airplane wreckage.


Koufonisia: Spend a magical night in Koufonisia under the stars and enjoy a delectable dinner at one of the best local restaurants. In the morning, enjoy the splendor of hiking the southern shore of Koufonisia to a breathtaking bay where the skipper will meet you with the boat. Welcome to paradise!


Milos and the neighboring island Kimolos: With 70 beaches, the volcanic island of Milos has an unrivalled natural beauty that can be explored from the turquoise waters that surround it. You’ll visit the breath taking Kléftiko (the iconic landscape that defines the Cyclades in so many travel books), work your way up the quiet west coast of the island, and marvel at the white rocky, lunar landscape of Sarakíniko. Late afternoon, on the island of Kimolos, we’ll explore the quaint, colorful sirmata (cave-like structures that used to store boats) and the little town, level with the water while we wait for the sunet and a feast.


Mykonos: One of the most popular destinations of our Cyclades sailing tours, Mykonos, according to Greek mythology, was formed from the petrified bodies of giants killed by Hercules and named after Apollo’s grandson. Stroll through the narrow marble streets with their whitewashed houses with colorful doors and window frames contrasted by its bougainvillea trees in purple bloom. Explore the many pedestrian shopping streets with hidden churches, cafés, restaurants, and nightclubs. Don’t forget to visit the lively waterfront restaurants and “Little Venice”. In the morning enjoy retracing your steps through the meandering streets of Mykonos before setting sail.


Naxos: Naxos, the largest island in the Cyclades, has something for everyone: sightseeing (including the gate to the ancient Temple of Apollo, the Temple of the Goddess Dimitra, and a Venetian castle), cycling along the miles of beaches on the southwest coast, bars, restaurants, and narrow shop lined streets.

Tip: Ask your skipper where to find the fancy drinks with sparklers. They make you feel like it’s your birthday and new years eve at the same time, every time.


Paros: This island has it all: sightseeing in the capital of Parikia (Venetian castle, church with 100 doors, an Orthodox baptistery, and monastery), Byzantine footpaths connecting traditional villages, breathtaking landscapes, canoeing / kayaking, tranquil beaches, free red and green clay natural spa, a picturesque fishing town with a vibrant nightlife, and a valley full of butterflies.

Schinoussa: Possibly named after a bushy plant found on this island, the schino, this quiet island offers scenic footpaths, beautiful beaches, caves, remains of a medieval castle, and a delicious, wholesome cuisine.

Serifos: Take in the breathtaking sunset views from what seems like the top of the world: the Church of Agios Konstantinos.  We’ll sped the night exploring the traditional mountain top village and its meandering walkways, ouzarias, and restaurants. A traditional fish or meat dinner is not to be missed in the tavernas on the beach by the port.


Sifnos: Take in the cosmopolitan, sandy beaches and seaside shops of Sifnos and a scrumptious light lunch.


Syros: Meaning the city of Hermes, the capital town of Ermoúpoli boasts neoclassical houses, unique shops, and beautiful squares. Take the stairs up to the medieval quarter of the Roman Catholic community and the fortress-like St George’s cathedral which offers breathtaking views of the island.

The best time to go on a Cyclades sailing trip, if you never sailed before, is during May, June and September. In July and August the winds can be strong, which is great for sailing but not so enjoyable if one suffers from sea sickness.


Reserve now, adventure awaits.

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