experiences

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

6 departures available

September - October

Starting from

€1,300

€1,040

Per person

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€570

Per person

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

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

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

4.3

New

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

September - October

Starting from

€890

Per person

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

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

5.0

Super!

From Skiathos to Athens

Greece: Sporades

7 days - 7 nights

One departure available

September

€620

Per person

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

4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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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

1941 reviews

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

09/1/2026

CRISTINA G.

I thank Alessandro and Carlo for the wonderful holiday, as well as my travel companions with whom I had a very good time. Wonderful coves and very characteristic villages. Too bad there was no wind to be able to sail more. The boat is spotless and equipped with sup and tender always available.

Sailing cruise in the Greek islands - The Saronic Islands

08/31/2026

Silvia Maddalena V.

First sailing holiday with Sail Square to the Saronic Islands and it was a great experience. The platform is intuitive and the organization is working. A special thanks to our skipper, always flexible in complying with our requests on the routes and on the choice of sleeping at anchor, and patient in explaining the basics of navigation, making my first time on a boat unforgettable. A week of pure relaxation in wonderful places. Highly recommended!

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

08/31/2026

Giuseppina F.

Third flotilla experience with different sailing. After the Aeolian and Pontine Islands, Ionian Greece was also a wonderful holiday. A rich and dynamic itinerary. Fantastic group on board Tango I and super positive experience especially thanks to the great professionalism, availability and kindness of the Skipper Vincenzo and the coskipper Nina! Our added value!

Sailing among the Islands of Ulysses. Stewardess on board

08/31/2026

Chiara Alessandra P.

Great experience. Leonor is a magnificent commander and Hansel a great cook. We had fun 🐬

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