
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!
96
experiences

4.7
Greece: Cyclades
6 days - 7 nights
One departure available
August
€1,290
€1,190
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
10 departures available
August - October
Starting from
€1,400
€1,120
Per person

4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
8 departures available
August - October
Starting from
€2,500
€2,250
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
8 departures available
August - October
Starting from
€570
Per person

5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
10 departures available
August - October
Starting from
€570
Per person

4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
One departure available
August
€800
Per person

4.8
Super!
Greece: Cyclades
7 days - 7 nights
6 departures available
August - November
Starting from
€1,000
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
12 departures available
August - November
Starting from
€700
€665
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
4 departures available
July - August
Starting from
€1,800
€1,440
Per person

4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
One departure available
September
€650
Per person

5.0
Super!
Greece: Ionian Islands
6 days - 7 nights
One departure available
July - August
€1,900
Per person

4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
September - November
€585
€527
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
1967 reviews
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
07/25/2026
francesca b.
-
IT
Big and luxurious 60ft catamaran in Saronic Islands - best local experiences
07/25/2026
Matthias S.
-
IT
Catamaran week among the islands of Ionian Greece
07/24/2026
Francesco B.
-
IT
The most spectacular islands of the Cyclades: from Athens to Milos
07/23/2026
Frank W.
-
DE
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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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