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

5 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

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

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

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

4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

€750

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

4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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

5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

4.8

Super!

Come sail with us in the Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€600

Per person

4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€600

Per person

Why book a holiday with Sailsquare?

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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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Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

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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

1953 reviews

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

09/9/2026

Parmentier S.

We had a very pleasant time, a very nice captain and hostess, a super nice doggie, a very nice boat, wonderful weather and blue everywhere, the dream.

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

09/9/2026

Elisabetta M.

WONDERFUL: this word can give you an idea of what awaits you on a holiday like this. It was an unforgettable week, in the middle of the sea, with fantastic people I didn't know and an absolutely unique skipper! Alessandro is the skipper that everyone would like, punctual, a profound connoisseur of the sea, an excellent cook and an unforgettable storyteller! We were lulled by the sea, we ate delicious food and, last but not least, the comets kept us company! I would leave immediately... thanks also to my extraordinary travel companions!

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/8/2026

Cecile G.

Fantastic experience and week of sailing!

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/7/2026

Salvatore Giuseppe Antonio S.

Beautiful holiday with Gianfranco captain skipper always available and company for a wonderful tour of the islands in the name of relaxation, snorkeling and fun. Recommended for everyone

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