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Sailboat yacht sailing holidays & tours in Greece

Discover more than 39 opportunities to get on board a Sailboat adventure in Greece. 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

7 departures available

August - October

Starting from

€1,300

€780

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

4 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

5 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

5 departures available

September - November

Starting from

€585

€527

Per person

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4.8

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

€600

€540

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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4.8

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!

From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

€950

Per person

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4.2

New

Dreamy Saronics: turquoise waters and relaxation just a stone's throw from Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€990

€842

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

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.

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

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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 - Sailboat yacht sailing holidays & tours in Greece

1911 reviews

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Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/24/2026

Walter B.

-

IT

Relaxation, fun, laughter and beautiful people. Dani, a prepared skipper who is always on point, and Alice, impeccable in coordinating the group: a perfect match. Thanks also to the special correspondents of Marmaglia TV!
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Different flotilla in Ionian Greece: nature, new friends and fun

08/24/2026

Gennaro P.

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IT

Safety, professionalism and big laughs. Bringing together people who don't know each other on a boat is never trivial, but Roberto and Antonio were exceptional. They were able to steer the boat with great skill and at the same time create a relaxed, fun (we laughed a lot) and inclusive atmosphere. Roberto manages every situation at sea with exemplary calm and competence, flanked by an impeccable Antonio who is always on point. A wonderful week that I will carry inside me for a long time. Thank you both very much!
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Different flotilla in Ionian Greece: nature, new friends and fun

08/24/2026

Marta S.

-

IT

Roberto Trinari and Mike, impeccable skipper and co-skipper and an integral part of our fantastic crew. After 5 min of acquaintance he seemed to be friends of a lifetime! Beautiful places and dream sea!!

Different flotilla in Ionian Greece: nature, new friends and fun

08/24/2026

Livia Paolina C.

-

IT

A week of fun and beautiful sea. The preparation, seriousness and immense sympathy of skipper Roberto Trinari and assistant skipper Antonio Testa helped to create a beautiful atmosphere on the boat.

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