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Yacht sailing holidays & skippered tours in Greece

Discover more than 58 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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4.8

Super!

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

4 departures available

August - September

Starting from

€1,300

€1,040

Per person

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4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

August - October

Starting from

€2,700

€1,890

Per person

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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

€570

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

3 departures available

September - October

Starting from

€570

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€585

€527

Per person

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4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

€1,000

Per person

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4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - October

Starting from

€700

€665

Per person

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4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

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5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

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4.9

Super!

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€990

Per person

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4.8

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

August - October

Starting from

€900

Per person

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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

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

2003 reviews

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Sailing among the Islands of Ulysses. Stewardess on board

08/8/2026

Francescu G.

-

FR

A very pleasant trip. Hansel and Éléonore are adorable, knew how to make us discover magnificent coves, listen to the passengers and take into account everyone's desires. We highly recommend!!

Catamaran week among the islands of Ionian Greece

08/7/2026

Kristina S.

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DE

Nicolo is a wonderful person. He is a very experienced, passionate and thoughtful skipper who knows his sailing territory very well. He makes the crew feel like home on board. The boat is very comfortable and very well equipped. We saw the most beautiful spots in the Ionian Sea while spending lots of fun time with Nicolo and our lovely crew. Thank you for this amazing experience!

Sailing cruise in the Greek islands - The Saronic Islands

08/5/2026

Donatella M.

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IT

The sea, the sun, the wind are nothing without a good captain and Periklis has proven to be one in all circumstances and above all human expectations.
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Whale watching cruise with WWF guide in the Corfu archipelago

08/3/2026

Carlo P.

-

NL

It was what I wanted

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