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Wishing for a sailing holiday with your family? Time to make your dream come true.

166 available holidays

Discover real nature on a sailboat.

472 available holidays

All-Inclusive sailing holidays: just relax and enjoy life onboard.

183 available holidays

Discover your own holiday style. Browse and be inspired.

Top destinations.

Italy

1076 holidays

Tuscany

138 holidays

Aeolian Islands

200 holidays

Pontine Islands

76 holidays

Northern Sardinia - Maddalena Archipelago and the Costa Smeralda

200 holidays

Croatia

128 holidays

Liguria

111 holidays

Greece

388 holidays

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from the blog

5 Greek islands that few people know: discover them on a sailing boat!

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Sailsquare is the ultimate connection between skippers and travelers.

Skippers create holidays following their passions, the others will simply enjoy an unforgettable holiday.

Discover who is already on board before you leave!

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

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