Yacht sailing holidays & skippered tours in Greece
Discover more than 54 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
54
experiences
54
experiences
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
August - October
Starting from
€550
Per person
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
August - September
Starting from
€550
Per person
4.8
Super!
Greece: Ionian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€600
€540
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
3 departures available
September - October
Starting from
€650
€618
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
September
€1,050
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
4 departures available
August - October
€585
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
Starting from
€955
Per person
5.0
Super!
Greece: Cyclades
7 days - 7 nights
5 departures available
August - October
Starting from
€1,080
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
August - September
Starting from
€750
€638
Per person
5.0
Super!
Greece: Dodecanese
7 days - 7 nights
One departure available
September
€650
Per person
5.0
Super!
Greece: Cyclades
7 days - 6 nights
One departure available
September
€1,050
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
1748 reviews
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
06/11/2025
Gemma M.
-
Italy
Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades
06/7/2025
Denis P.
-
Italy
Corfu to Athens via the exciting Corinth Canal
06/7/2025
Irene A.
-
Italy
Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades
06/6/2025
Alessandra C.
-
United States
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