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!
18
experiences
4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
3 departures available
October
€2,350
Per person
4.8
Super!
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
2 departures available
October
€1,300
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
2 departures available
October - November
€585
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
2 departures available
October
€750
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
2 departures available
October
€570
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
3 departures available
October
€570
Per person
4.4
Premium
Greece: Saronic Islands and Athens area
7 days - 7 nights
26 departures available
May - October
Starting from
€1,305
€1,044
Per person - min 2 pax
4.2
Greece: Dodecanese
7 days - 7 nights
2 departures available
October
Starting from
€829
Per person
Greece: Ionian Islands
7 days - 7 nights
One departure available
October
€890
Per person
4.7
Greece: Saronic Islands and Athens area
7 days - 7 nights
4 departures available
October - November
€1,000
Per person
4.7
Greece: Saronic Islands and Athens area
7 days - 7 nights
5 departures available
October - November
€700
€665
Per person
4.2
Greece: Ionian Islands
7 days - 7 nights
2 departures available
October
Starting from
€779
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
2157 reviews
Corfu between bays, taverns and myths.
10/4/2026
Clara M.
-
ES
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
10/3/2026
Marina G.
-
IL
Corfù Paxos Antipaxos
10/2/2026
Ruta L.
-
LT
Fast Sailing Experience between Authentic Islands and Good Food
10/1/2026
Alexandra C.
-
CA
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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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