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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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5.0

Super!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

One departure available

July

€790

Per person

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4.9

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

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5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

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5.0

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Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

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5.0

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We will depart from Kos to head to Mykonos with a very comfortable boat

Greece: Cyclades

7 days - 6 nights

One departure available

September

€750

Per person

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4.9

Super!

Astypalaia, Anafi and Santorini: the pearls of the Southern Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€990

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

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4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.9

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

€750

€713

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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5.0

Super!

Seven days in the blue on the trail of Ulysses

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,000

€950

Per person

Why book a holiday with Sailsquare?

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The world's largest marketplace for sailing holidays

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

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 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

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

1790 reviews

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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/18/2025

Nathalie B.

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France

All the will Suddenly he leaves Faced with the obvious All this is immensity And work for 10 hours Always make choices of the heart Apologizing for a mistake This too is immensity All reality is immensity How the dream will then dissolve From tomorrow a new immensity will begin again From tomorrow From tomorrow From tomorrow •• Andrea Lazlo de Simone . Immensity And so, the mermaids disguised themselves as a birthday Elvis, the sea played at being the ocean and sailing did not challenge the fury of a capricious eole! New Odyssey, on a new parallel. For a parenthesis ... 'insolent'. And everything was ... immensity! Σας ευχαριστώ . Καλό ταξίδι …
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/17/2025

Lucilla C.

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United Kingdom

A 5 star experience! Went with my partner and two friends, we were very lucky at clicking so well with the other two passengers and by the end of the week we had so much fun we decided to stay in touch. The places we visited were breathtaking, our skipper Alessandro was the warmest ever, he took good care of us and was always making sure we were comfortable. Five stars also to Carlo who was prepping us delicious food and making sure we didn't move a finger and enjoyed the holiday (despite our attempts to help!). They have SUPs that we were able to use, masks for snorkeling, we went looking for sea urchins and we saw plenty of fish (even barracudas!). The moments we went only with the sail and no enigne were magical. We will definitely do it again!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/14/2025

Claudia Z.

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Italy

Seven days, one boat, a thousand emotions We spent a wonderful week on a sailing boat exploring the beauties of Corfu and the nearby islands, guided by a skipper who was truly out of the ordinary: Andrea. It is evident that he deeply loves his job – competent, professional, capable of transmitting confidence and serenity even when the weather has decided to throw a tantrum. Two days of forced stop in port could have ruined the spirit of the trip, but Andrea was able to turn everything into an opportunity to discover, learn and relax. Always ready with a kind word, interesting information or a joke at the right time, he did much more than you would expect from a skipper, including top info about the restaurants! Also on board with us was Carlo, a discreet and attentive steward, who with his caring presence made life on board even more comfortable. The boat, spacious and comfortable, was our perfect floating retreat. And Mattias, the poodle on board? A sweet cuddle that conquered everyone, including the most insensitive to hairy faces. An added value was the proximity of the boat of Andrea's brother, Alessandro: this allowed us to get to know the participants of his boat and to share very pleasant moments together, including aperitifs, laughter and chats under the stars. If I really have to find a point on which to suggest an improvement but it is a constructive personal thought: it is the kitchen. With a little more focus on variety, ingredient quality, and presentation, the experience could really level up. Because, let's face it, customers are often won over even with just a well-thought-out dish! That said, it was a holiday full of excitement, beautiful scenery and great company. We would gladly do it again and I will over-recommend it to friends at home – maybe without wind, but always with Andrea at the helm!
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The alternative to the catamaran in the Sporades

07/14/2025

Pietro M.

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Italy

The sailing experience with Manuele was magical. He is a formidable captain, attentive to everything around him, always transmitting confidence and passion in everything he does. An exceptional chef who surprises you every day with his dishes. Being able to share this experience with him was a privilege that I wish for everyone. He made me fall in love with sailing, I will definitely come back with him for more adventures.

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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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