Sailboat and catamaran: the guide to sailing with a skipper

Destinations, inspiration, and life on board: all you need to know about sailing holidays with a skipper

Contrary to popular myth, sailing holidays are not reserved only for the rich, well-connected, or veteran sailors - Sailsquare offers the opportunity to set sail with a skipper.
Sailing holidays are now accessible to all, a new way of holidaying is born.


Escape from the crowds, travel in the lesser-known areas, and live a unique holiday experience. We at Sailsquare have produced this sailing holiday guide to help travellers unlock the potential for their dream trip.

Sailsquare, the sharing economy sailing holiday platform

Sailsquare is Europe’s #1 for sailing holidays by sailboat and catamaran. The platform connects curious travellers, with more than 2,600 skippers around the world. Sailsquare lists a host of sailing holidays matching all different preferences and budgets, with weekend trips starting from €100, and week-long trips starting at €400.

With 95 destinations around the world, including: Greece, Croatia, Balearic Islands, Italy, Turkey, Caribbean, Seychelles, Thailand, Norway, Malta.