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!
61
experiences
4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
8 departures available
August - October
Starting from
€1,300
€910
Per person
4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
7 departures available
August - October
Starting from
€2,500
€2,250
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
5 departures available
September - October
Starting from
€570
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
7 departures available
August - October
Starting from
€570
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
September - November
Starting from
€585
€527
Per person
4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
September
€650
Per person
4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
3 departures available
August - October
Starting from
€900
Per person
4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
3 departures available
September - October
Starting from
€600
€540
Per person
5.0
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
September
€650
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
3 departures available
September - October
€750
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
2 departures available
August - September
Starting from
€1,125
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
2036 reviews
Different flotilla in Ionian Greece: nature, new friends and fun
08/18/2026
Flavia U.
-
IT
Luxury catamaran cruise in the Cyclades
08/18/2026
Paolo F.
-
CH
Sailing cruise in the Greek islands - The Saronic Islands
08/18/2026
Catherine B.
-
FR
From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat
08/18/2026
Alix R.
-
FR
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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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