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!
59
experiences
59
experiences
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
August - October
Starting from
€550
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
August - October
Starting from
€550
Per person
5.0
Super!
Greece: Cyclades
7 days - 7 nights
3 departures available
September - October
€1,080
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
4 departures available
September - November
Starting from
€650
€618
Per person
5.0
Super!
Greece: Dodecanese
7 days - 7 nights
2 departures available
September
Starting from
€650
Per person
5.0
Super!
Greece: Cyclades
5 days - 5 nights
3 departures available
August - September
Starting from
€900
€810
Per person
5.0
Super!
Greece: Dodecanese
8 days - 8 nights
One departure available
September
€650
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August - September
€955
€790
Per person
4.8
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€955
Per person
5.0
Super!
Greece: Ionian Islands
6 days - 6 nights
One departure available
September
€900
Per person
5.0
Super!
Greece: Cyclades
7 days - 6 nights
One departure available
September
€750
Per person
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Get onboard solo, with your family or your friends
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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
1825 reviews
From Paros to Milos, the hidden gems of Cyclades
08/16/2025
lorenzo k.
-
Italy
South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca
08/13/2025
Damiano C.
Short trip around Paros and the small Cyclades
08/11/2025
Francesca B.
-
Italy
Secret Aegean with skipper and kitchen on board from Rhodes to Kos
08/10/2025
BARBARA C.
-
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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