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Crewed yacht sailing holidays & tours in Greece

Get on board on a crewed sailing holiday in Greece for the most relaxed time ever.

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€550

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

€790

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

€790

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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4.7

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

8 departures available

August - October

Starting from

€1,100

€1,045

Per person

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€550

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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5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.9

Super!

Corfu - Lefkada ONE WAY: an exclusive adventure with hostess on board

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€464

Per person

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4.8

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August - September

Starting from

€1,150

€950

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€1,260

Per person - min 2 pax

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€2,100

€1,995

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Crewed yacht sailing holidays & tours in Greece

226 reviews

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Fast cruising Cicladi Occidentali

08/26/2025

Sergio B.

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Italy

Annalisa and Lorenzo are first and foremost two wonderful people. Then they are two very experienced sailors: they have sailed around the world; they know the waters of the Aegean by heart. Finally, they are also great as cooks: where do you find the barbecue on the boat and the freshly hand-pulled egg pasta below deck? Only from them! The bays where they took us were breathtaking.
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

08/25/2025

Laura C.

-

Italy

Beautiful week
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/24/2025

David C.

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Germany

Alessandro, the skipper, is not only highly prepared professionally, but also extremely polite and attentive to the needs of each passenger. We never had to cook, wash dishes or make ourselves a coffee: Carlo took care of everything with great care. It felt more like being in a floating hotel than on a sailboat. The itinerary is wonderful and well tested. Both Alessandro and his brother (skipper of the other boat that accompanied us throughout the trip) have known him for many years, and it shows. The dog Eros was also a very pleasant company, adding a special touch to the experience. Often in the evening, after a day spent in the water, we enjoyed relaxing walks on the islands visited, a perfect way to stretch our legs and experience the atmosphere of the place even more.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

08/20/2025

Gaia C.

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Italy

First experience on a sailing boat for us and we are very happy to have had it with Alessandro and Carlo. Alessandro is prepared, helpful and an extremely kind person. The places chosen for the tour and the organization in general made us feel always in excellent hands. Carlo's presence is a plus for sympathy and professionalism!

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