Sailsquare | N°1 in Europe for sailing and catamaran holidays

Andrea A.

Provider type:

Organisation

City:

Sicily

Member since:

2026

Gallery

Show all

About us

We love sharing the magic of sailing through the Aeolian Islands. Departing from Portorosa Marina in Sicily, these sailing holidays and cabin charters take you across one of the most beautiful archipelagos in the Mediterranean.

Each trip is designed to let you discover the islands at a relaxed pace — sailing between volcanic landscapes, swimming in crystal-clear waters, exploring small island villages, and enjoying sunsets from the deck of a comfortable sailing yacht.

Whether you’re traveling solo, with friends, or looking to meet other sea lovers, these experiences combine adventure, nature, and the simple pleasure of life at sea, with a focus on creating a welcoming atmosphere onboard and unforgettable memories while exploring the Aeolian Islands by sail.

My boats

Type

Sailboat

Length

14.94 m.

Toilets

Cabins

12+

Show all

Travel with peace of mind

Total transparency

Want to avoid surprises? Find out before you book who your skipper and fellow travellers will be. Do you have questions or doubts? Send a message to the skipper!

Flexible cancellation

Cancel within 30 days of departure for any reason and receive a full refund. Want even more? Purchase the extension to cancel your booking until your departure.

Constant support

Our dedicated multilingual support team is always ready to assist you, before and during your holiday, and is always in touch with the skippers we work with.