Yacht sailing holidays & skippered tours in Greece
Discover more than 51 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
51
experiences
51
experiences
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€550
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€550
Per person
4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
August - September
Starting from
€600
€540
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
2 departures available
July - August
Starting from
€650
€618
Per person
4.9
Super!
Greece: Cyclades
13 days - 14 nights
One departure available
August
€2,050
Per person
4.7
Premium
Greece: Cyclades
6 days - 7 nights
One departure available
August
€2,947
€2,800
Per person
5.0
Super!
Greece: Cyclades
7 days - 7 nights
2 departures available
August - September
Starting from
€1,080
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
One departure available
August - September
€585
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August
Starting from
€955
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
August
Starting from
€800
€720
Per person
4.9
Super!
Greece: Ionian Islands
6 days - 7 nights
One departure available
August
€1,150
€950
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August
€1,050
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
Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.
Find out before you book who's waiting for you on board
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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
1752 reviews
Corfù Paxos Antipaxos
06/16/2025
Marie Claude H.
-
France
Fast sailing holiday in the Cyclades with gourmet cuisine on board
06/15/2025
Alberto L.
-
Italy
Cyclades and Microcyclades with a magnificent 15-meter boat
06/15/2025
Ester L.
-
Italy
Pack your suitcase and we'll take care of the rest!! Stewards on board!
06/15/2025
Diego D.
-
Austria
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