Yacht sailing holidays & skippered tours in Greece
Discover more than 59 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.
59
experiences
59
experiences
5.0
Super!
Greece: Ionian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€550
Per person
4.9
Super!
Greece: Ionian Islands
7 days - 7 nights
4 departures available
August - October
Starting from
€550
Per person
4.9
Super!
Greece: Saronic Islands and Athens area
7 days - 7 nights
2 departures available
September
Starting from
€650
€618
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August - September
€955
Per person
5.0
Super!
Greece: Cyclades
7 days - 7 nights
4 departures available
August - October
Starting from
€1,080
Per person
4.8
Super!
Greece: Saronic Islands and Athens area
6 days - 6 nights
4 departures available
August - October
Starting from
€585
€497
Per person
4.8
Greece: Ionian Islands
7 days - 7 nights
3 departures available
August - September
Starting from
€600
€540
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
Per person
5.0
Super!
Greece: Dodecanese
7 days - 7 nights
2 departures available
September
Starting from
€650
Per person
5.0
Super!
Greece: Dodecanese
7 days - 6 nights
One departure available
September
€1,050
Per person
5.0
Super!
Greece: Cyclades
7 days - 6 nights
One departure available
September
€750
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€955
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
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
1776 reviews
Pack your suitcase and we'll take care of the rest!! Stewards on board!
07/7/2025
Diana U.
-
Italy
From the Dodecanese to the Cyclades: sailing off the beaten track!
07/7/2025
Farida B.
-
Italy
From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat
07/7/2025
Maddalena D.
-
Italy
Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?
07/7/2025
Virginia B.
-
Italy
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