Sailboat yacht sailing holidays & tours in Cyclades
Discover more than 32 opportunities to get on board a Sailboat adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.
32
experiences
32
experiences
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
7 departures available
August - October
Starting from
€1,080
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€870
Per person
5.0
Super!
Greece: Cyclades
7 days - 6 nights
One departure available
September
€750
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
August
€990
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€955
Per person
4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€835
Per person
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
€790
€711
Per person
4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€800
Per person
Greece: Cyclades
5 days - 5 nights
2 departures available
August - September
Starting from
€900
€765
Per person
4.9
Greece: Cyclades
13 days - 14 nights
One departure available
August
€2,050
Per person
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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 - Sailboat yacht sailing holidays & tours in Cyclades
356 reviews
One way from the Cyclades to the Dodecanese on a magnificent 15-meter boat
06/29/2025
Gabriele A.
-
Italy
Secret Aegean with skipper and kitchen on board from Santorini to Kos
06/26/2025
Melissa C.
-
Italy
We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea
06/25/2025
Anna M.
-
Luxembourg
Secret Aegean with skipper and kitchen on board from Santorini to Kos
06/24/2025
gina c.
-
United States
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