Thousands of unique sailing holidays, organised by local skippers.
Alfredo C. 5 minutes ago
Martina R. 13 minutes ago
Alfredo C. 16 minutes ago
Elena M. 21 minutes ago
Elena M. 24 minutes ago
Corinne B. 37 minutes ago
Sunshine A. 
Santo S. 
Hartmut L. 
Alessandro D. 59 minutes ago
Ilaria M. 1 hour ago
Carlo F. 1 hour ago
Raffaella C. 1 hour ago
Raffaella C. 1 hour ago
Roberto & Giusy B. 1 hour ago
Alessandro F. 
Costanza S. 
PIETRO M. 
Top destinations.
Italy
1995 holidays
Greece
522 holidays
Northern Sardinia
398 holidays
Aeolian Islands
361 holidays
Tuscany
307 holidays
Pontine Islands
228 holidays
Croatia
226 holidays
Liguria
149 holidays
Sailsquare 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.
We're here to help you before, during and after your holiday.
You can contact our customer care team, or contact your skipper directly. We're all here to help offer support and guidance!
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