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!
124
experiences
4.8
Super!
Greece: Ionian Islands
6 days - 7 nights
4 departures available
September - October
Starting from
€600
€540
Per person
4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
July
€1,000
Per person - min 2 pax
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€835
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€750
Per person
5.0
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
September
€650
Per person
5.0
Super!
Greece: Ionian Islands
6 days - 6 nights
One departure available
August - September
€900
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,080
Per person
4.9
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
July
€1,000
Per person - min 2 pax
5.0
Super!
Greece: Sporades
10 days - 10 nights
One departure available
August
€1,250
Per person
5.0
Super!
Greece: Ionian Islands
6 days - 6 nights
2 departures available
September
€900
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
8 departures available
August - November
Starting from
€1,000
Per person
Greece: Ionian Islands
7 days - 7 nights
3 departures available
July - October
Starting from
€779
Per person
Why book a holiday with Sailsquare?
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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.
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
1944 reviews
Corfu between bays, taverns and myths.
07/9/2026
Loredana L.
-
IT
Corfu between bays, taverns and myths.
07/8/2026
Farida B.
-
IT
Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays
07/7/2026
Giorgio R.
-
FR
Corfu between bays, taverns and myths.
07/6/2026
Stefano C.
-
IT
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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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