
Yacht sailing holidays & skippered tours in Greece
The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!
71
experiences

4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
4 departures available
September - October
Starting from
€600
€540
Per person

5.0
Super!
Greece: Ionian Islands
6 days - 6 nights
One departure available
August - September
€900
Per person

5.0
Super!
Greece: Ionian Islands
6 days - 6 nights
10 departures available
August - November
Starting from
€1,099
Per person

4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
August
€1,200
Per person - min 2 pax

5.0
Super!
Greece: Ionian Islands
6 days - 6 nights
One departure available
September
€900
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
3 departures available
September - October
Starting from
€750
€713
Per person
5.0
Super!
Greece: Cyclades
6 days - 6 nights
2 departures available
September
€1,000
Per person

5.0
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
One departure available
September
€620
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August
€1,075
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,080
Per person

5.0
Super!
Greece: Sporades
7 days - 7 nights
One departure available
September
€620
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€800
Per person - min 2 pax
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.
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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
2007 reviews
Whale watching cruise with WWF guide in the Corfu archipelago
08/10/2026
Marco C.
-
IT
Sailing paradise in Greece on a big 50 ft boat: the best local experience
08/9/2026
Sofia Z.
-
BE
South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca
08/9/2026
Gloria G.
-
IT
Catamaran in the Saronic Islands: Hydra, Poros, Aegina and wild bays
08/9/2026
Silvia D.
-
IT
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Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat
Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat
Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat
Greece: the most beautiful places to sail
Greece: departures by month
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