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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

4 departures available

September - October

Starting from

€600

€540

Per person

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5.0

Super!

Kefalonia to Corfu

Greece: Ionian Islands

6 days - 6 nights

One departure available

August - September

€900

Per person

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5.0

Super!

Catamaran week among the islands of Ionian Greece

Greece: Ionian Islands

6 days - 6 nights

10 departures available

August - November

Starting from

€1,099

Per person

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4.9

Super!

Rhodes Kalymnos South Dodecanese on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,200

Per person - min 2 pax

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5.0

Super!

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

September

€900

Per person

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€750

€713

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,075

Per person

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4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,080

Per person

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5.0

Super!

From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Greece

2007 reviews

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Whale watching cruise with WWF guide in the Corfu archipelago

08/10/2026

Marco C.

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IT

It was a fantastic experience. Very nice. WWF skipper and guide simply wonderful. Certainly to be repeated. Thank you Thank you Thank you
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Sailing paradise in Greece on a big 50 ft boat: the best local experience

08/9/2026

Sofia Z.

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BE

Great sailing and holiday experience with amazing skipper and hostess.

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

08/9/2026

Gloria G.

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IT

As a first sailing experience, everything was perfect exceeding expectations. Frank was an excellent skipper, he welcomed us on his boat with extreme professionalism and sympathy, he knew how to listen to our needs and made us discover wonderful places. We highly recommend this experience. fair winds!

Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays

08/9/2026

Silvia D.

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IT

I was lucky enough to sail in the crystal clear and windy waters of Greece with Andrea and from the first moment I appreciated his great desire to transmit and share his knowledge of the sea and "skippering". Safety, professionalism and attention to any need made this experience truly special. Andrea manages to make you feel at home even in the middle of the sea, transmitting tranquility, passion and competence. The choice of destinations and itinerary proposals also made the difference, allowing us to discover wonderful places and experience the sea in an authentic way. But the real difference, in experiences like this, is made by the people: Andrea and the 8 travel companions have helped to create a fantastic group, made up of sharing, laughter, new friendships and moments that I will take with me. A holiday that was not simply a catamaran holiday, but an experience to live and remember. Absolutely to be repeated! 💙⛵️🇬🇷

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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

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