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Choose your sailing holiday among thousands of unique experiences.

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Travel solo or in group and discover your next sail mates.

Our favorites.

Discover other 241 available holidays now!

Weekend d'autunno in barca: veleggiate, tramonti mozzafiato e serate sotto le stelle.

58 available holidays

Scegli una destinazione esotica per il tuo Capodanno in barca a vela: Carabi o Tailandia?

4 available holidays

L'estate va avanti, trova il tuo weekend in barca a vela!

18 available holidays
Discover your own holiday style. Browse through all inspirations.

Top destinations.

Tuscany

47 holidays

Italy

172 holidays

Liguria

65 holidays

Caribbean

23 holidays

Pontine Islands

7 holidays

Venice and Trieste Gulf

14 holidays

Greece

15 holidays

Croatia

1 holidays

Discover all destinations.
from the blog

Sailing holidays: embrace a peaceful state of mind

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We are the first common ground between skippers and travelers.

Skippers create holidays based on their passions, the others are just busy enjoying their holiday.

Discover who is already on board before leaving!

Meet on Sailsquare, get to know each other on the boat and get home with a lot of new friends.

Do you need help, before, after or during the holiday?

You can contact our customer care or directly the skipper who created the holiday. We're here for you!

Still uncertain? Give us some details, we are looking forward to help you finding your perfect holiday! Fill in the form!