header cover
logo

Log in

Crewed yacht sailing holidays & tours in the Aeolian Islands

Get on board on a crewed sailing holiday in Corse for the most relaxed time ever.

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Crewed yacht sailing holidays & tours in the Aeolian Islands

221 reviews

Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/9/2026

Vincenzo F.

-

IT

Fantastic week. Perfect organization, hospitality and kindness are guaranteed. Giorgio and Diego excellent "hosts".
avatar image

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

09/8/2026

Stefania P.

A week on a catamaran in the Aeolian Islands that I will hardly forget! ⛵️🌊 Andrea, our skipper, and Arianna, our hostess, were just amazing. Andrea is a real guarantee: competent, quiet and solid, he knows the Aeolian Islands and their sea like the back of his hand. He took us to discover wonderful places making us feel always in excellent hands. Arianna was very attentive to everything and everyone, always present and available. It was enough for someone to pronounce the word "beer?" and Arianna had already uncorked and made cheese, olives and taralli appear. They definitely spoiled us even at the table: delicious fish, pasta, vegetables, salads, wine... We really didn't miss anything. We discovered the Aeolian Islands from a wonderful perspective: during the day from the sea, between bays, dives and incredible views, and in the evening going ashore for a walk, a granita or an aperitif. One of the moments that I will definitely take with me is Stromboli: the sea crossing at sunset and the spectacle of the Sciara del Fuoco seen from the catamaran were exciting and evocative, difficult to describe in words. To make this holiday even more special was also the group I was lucky enough to find. People who a week earlier were strangers and with whom, between laughter, life on a boat, aperitifs and shared moments, a beautiful understanding was created. I left for a week in the Aeolian Islands and came back with many more memories than I thought I would pack. ❤️ Thank you Andrea, Arianna and the whole group for making this experience so special. I would do it again tomorrow! Greetings from Paris 😉
avatar image

Aeolian Islands on a catamaran, professional skipper/hostess, what else?

09/8/2026

Rosita L.

-

IT

Much more than just a holiday! An unforgettable experience where nothing is left to chance. Everything bordered on perfection, from the itinerary to the food (impeccable raw material and preparation, restaurant-like, if not better!), from the moments on board to those on land. Andrea is an expert navigator and a great connoisseur of the area, you can only trust him and rely on him to spend a dream week. To make everything even more relaxing the constant care of Arianna, the hostess, a discreet presence and attentive to everything, from morning to evening! Also unexpected was the wonderful group of people with whom I was lucky enough to share the experience. In short, expectations were very high and all were abundantly exceeded!
avatar image

Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/7/2026

Barbara R.

-

IT

Days of pure relaxation, the skipper Giorgio and the cook Diego made us spend a fantastic week, pampering us and making us discover the wonders of these islands. Thanks guys!

Customer Support

customer support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964