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Yacht sailing holidays & skippered tours in Greece

Discover more than 19 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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

2 departures available

October

Starting from

€550

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

October

Starting from

€550

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

€1,080

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October - November

Starting from

€650

€618

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

3 departures available

October

Starting from

€1,100

€1,045

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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4.8

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

€750

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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5.0

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

2 departures available

October

€990

Per person

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4.5

CYCLADIC ESCAPE - Active Holidays: 5 days Sailing & Exploring Unknown Greece  

Greece: Cyclades

4 days - 4 nights

One departure available

October

€790

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

One departure available

October

Starting from

€1,260

Per person - min 2 pax

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Autumn Gems of Cyclades away from the crowds on 51 ft yacht

Greece: Cyclades

7 days - 7 nights

One departure available

October

€580

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 - Yacht sailing holidays & skippered tours in Greece

1827 reviews

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

08/17/2025

Andrea C.

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Italy

It was an extremely pleasant holiday, discovering the wild nature of the islands and the crystal clear waters of the bays where we stopped. Francesco the skipper is very professional and competent and was also a great travel companion, always very helpful and always put us at ease. It was nice to be able to sail at any time when wind and weather allowed it.
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/17/2025

Maxime M.

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Italy

What a wonderful week with Aga, Greg and the other travellers. Magnificent landscapes of course but also and above all a great crew who made us discover the less touristy places, delighted us with an exceptional cuisine and the boat is beautiful and very comfortable. Only positive. We will be back for sure!
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From Paros to Milos, the hidden gems of Cyclades

08/16/2025

lorenzo k.

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Italy

Perfect skipper both from a professional and human point of view. Super recommended
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

08/13/2025

Damiano C.

Positive experience for the beauty of the places. Above all, a special appreciation for skipper Francesco [hidden]. Experienced, safe, competent and always available with discretion to understand the needs of guests.

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