
Private yacht sailing holidays with skipper in the Cyclades
Visiting the Cyclades islands by hiring a sailboat will be one of the most beautiful experiences you can do. Choose between sailing, catamaran and gulet and let yourself be conquered by the contrast of the blue and white of Mykonos, Santorini, Paros and the Little Cyclades.
20
experiences

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
July - August
€900
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€835
Per person

4.8
Super!
Greece: Cyclades
7 days - 7 nights
7 departures available
August - November
Starting from
€1,000
Per person

5.0
New
Greece: Cyclades
7 days - 7 nights
One departure available
July
€1,050
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
August
€950
Per person
5.0
Super!
Greece: Cyclades
6 days - 6 nights
2 departures available
September
€1,000
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€1,080
Per person

5.0
Super!
Greece: Cyclades
6 days - 6 nights
One departure available
September - October
€950
Per person

4.9
Super!
Greece: Cyclades
7 days - 7 nights
One departure available
September
€750
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August - September
€1,025
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
August
€1,090
Per person

4.9
Super!
Greece: Cyclades
6 days - 7 nights
One departure available
September
€890
Per person
Why book a holiday with Sailsquare?
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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 - Private yacht sailing holidays with skipper in the Cyclades
85 reviews
The most spectacular islands of the Cyclades: from Athens to Milos
07/13/2026
Marcella F.
-
IT
From Mykonos to Milos
07/2/2026
Maximiliano S.
-
AR
In the heart of the Cyclades, from Milos to Athens (Lavrio)
07/2/2026
Christine H.
-
DE
From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen
06/24/2026
Cesare S.
-
IT
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