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!
102
experiences
102
experiences
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
September
€1,050
Per person
5.0
Super!
Greece: Cyclades
7 days - 6 nights
One departure available
September
€750
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
August
€990
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
August
€1,000
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€955
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
August
€1,000
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€835
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
October
€950
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
3 departures available
September - October
€750
€713
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€835
Per person
4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
July
€880
€836
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
August
€1,000
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
1772 reviews
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/6/2025
Dario B.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/6/2025
francesco f.
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/6/2025
Claudio S.
-
Italy
From Sicily to Greece crossing the Strait of Messina
07/6/2025
Barbara B.
-
Hungary
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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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