Thousands of unique sailing holidays, organised by local skippers.
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Top destinations.
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1710 holidays
Greece
625 holidays
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341 holidays
Aeolian Islands
284 holidays
Croatia
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Northern Sardinia
190 holidays
Pontine Islands
190 holidays
Liguria
131 holidays
Island hopping in Greece on a sailboat – like a pro: a letter from two experts
read allSailsquare offers an ultimate connection between skippers and travellers.
Skippers create holidays following their passion, travellers will be able to simply enjoy an unforgettable holiday.
Discover who is already on board before you set sail!
Introduce yourself on Sailsquare, get to know each other on board, go home with new friends.
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