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!
106
experiences
106
experiences
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
11 departures available
July - October
Starting from
€550
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
9 departures available
July - October
Starting from
€550
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
6 departures available
July - November
Starting from
€650
€618
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
September
€1,050
Per person
4.7
Premium
Greece: Cyclades
6 days - 7 nights
One departure available
August
€2,947
€2,800
Per person
5.0
Super!
Greece: Ionian Islands
6 days - 7 nights
2 departures available
July
€790
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
2 departures available
August - September
Starting from
€955
Per person
5.0
Super!
Greece: Cyclades
7 days - 7 nights
7 departures available
August - October
Starting from
€1,080
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
6 departures available
July - October
Starting from
€585
€497
Per person
4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
July
€800
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
Per person
5.0
Super!
Greece: Dodecanese
7 days - 7 nights
2 departures available
September
Starting from
€650
Per person
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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 - Yacht sailing holidays & skippered tours in Greece
1767 reviews
From Rhodes to Kos: the fantastic South Dodecanese
07/1/2025
Patrizia F.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
06/30/2025
Gilberto B.
-
Italy
From Rhodes to Kos: the fantastic South Dodecanese
06/30/2025
Silvia A.
-
Italy
From the Dodecanese to the Cyclades: sailing off the beaten track!
06/30/2025
elisabetta m.
-
Italy
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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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