Yacht sailing holidays & skippered tours in Greece
Discover more than 28 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
28
experiences
28
experiences
4.5
Greece: Cyclades
4 days - 4 nights
3 departures available
October
€790
Per person
5.0
Greece: Peloponnese
7 days - 7 nights
3 departures available
October
Starting from
€795
Per person
4.3
Premium
Greece: Saronic Islands and Athens area
7 days - 7 nights
2 departures available
October
Starting from
€1,260
Per person - min 2 pax
Greece: Cyclades
7 days - 7 nights
One departure available
October
€580
Per person
Greece: Cyclades
7 days - 7 nights
One departure available
October
Starting from
€997
€798
Per person
4.7
Premium
Greece: Saronic Islands and Athens area
6 days - 7 nights
3 departures available
October
€2,100
€1,995
Per person
Greece: Cyclades
7 days - 7 nights
One departure available
October
Starting from
€1,020
€816
Per person
4.5
Greece: Cyclades
9 days - 9 nights
One departure available
October
€1,980
Per person
5.0
Greece: Ionian Islands
6 days - 6 nights
One departure available
October
€750
Per person
5.0
Greece: Ionian Islands
7 days - 7 nights
4 departures available
October - November
Starting from
€732
Per person
5.0
Greece: Peloponnese
7 days - 7 nights
3 departures available
October
Starting from
€795
Per person
4.3
Greece: Cyclades
6 days - 7 nights
5 departures available
September - November
Starting from
€690
Per person
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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
Find out more about the skipper and travellers who have already booked the holiday, to find out more about the
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
1788 reviews
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
07/14/2025
Claudia Z.
-
Italy
The alternative to the catamaran in the Sporades
07/14/2025
Pietro M.
-
Italy
Sailing and Hiking in the Cyclades
07/14/2025
Marco P.
-
Italy
The alternative to the catamaran in the Sporades
07/14/2025
Ginevra S.
-
Italy
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