experiences

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 - November

Starting from

€550

Per person

5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

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

4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

4.8

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€790

€711

Per person

4.8

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

€1,100

€880

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

One departure available

October

€550

Per person

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

5.0

Super!

Paros-Naxos and Small Cyclades

Greece: Cyclades

5 days - 5 nights

One departure available

September

€900

Per person

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

€1,080

Per person

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

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

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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

1744 reviews

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

09/15/2025

Claudio S.

Italy

Unforgettable trip! Skipper and hostess were super skilled, kind and always available. Great food, stunning places, the magic of sailing and the best company on board. Couldn’t ask for more!

Sailing holiday with yoga and SUP in the Saronic islands

09/15/2025

Nina S.

Finland

Awesome week at sea. Elias knows all the best places to go to. It was just amazing to have this possibility to enjoy yoga, sailing, swimming, Greek food & culture in a relaxing & safe way with good company. I would definetily like to do this soon again.

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

09/14/2025

Madison T.

Canada

Wow wow wow. We had no idea what to expect when booking this trip, it exceeded every expectation. Alessandro is knowledgeable and kind, his passion for what he does shows. Carlo is sunshine in human form, the food he makes on board is incredible. Eros is the perfect addition to the boat. We felt so well taken care of the entire time. The weather was perfect early September with it being less hot than July/aug. The rooms in the boat are comfortable but it does get hot down there to sleep, I could see a usb fan being useful for sleeping. Do not hesitate to book this trip with sailing sunset.

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

09/14/2025

Giuseppe M.

Italy

Francis number 1. Reliable and aware skipper!

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