header cover
logo

Log in

Yacht sailing holidays & skippered tours in the Aeolian Islands

A holiday in the Aeolian Islands: Vulcano, Lipari, Salina, Panarea, Stromboli, Alicudi, and Filicudi - seven volcanic islands to be discovered by sailboat. A unique experience in which you will navigate between craters, geysers, volcanic rock rivers.

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 - Yacht sailing holidays & skippered tours in the Aeolian Islands

2279 reviews

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/29/2026

Gloris M.

-

IT

We had a wonderful week. The skipper Fabrizio, always very kind, made us feel safe with great professionalism and tried to satisfy all our requests compatibly with the weather. The hostess Monica, always discreet and patient, knew how to take care of the guests without being intrusive. He prepared tasty dishes that helped make the holiday even more enjoyable. If we could we would leave immediately for another holiday with this crew!

Conquering the Aeolian Islands - Cook on board

09/28/2026

Andrea N.

-

IT

Despite the unstable weather, fantastic week. Thank you Sergio and Carmen.

The Aeolian Islands aboard a fantastic Catamaran with Stewardess

09/28/2026

Rocco C.

-

IT

We had a great time on board ! Beautiful locations and well-made 🥰 food Fabrizio is a very experienced and attentive skipper. Monique too, our hostess was great! Always available and cooking really well! The whole experience was wonderful both for the places and for the company! We will have other experiences with them!
avatar image

Conquering the Aeolian Islands - Cook on board

09/28/2026

Marco C.

-

IT

Very nice experience thanks to the seriousness of Sergio and Carmen who always made us sail safely despite the weather on some days was hostile, as well as creating a cheerful environment and a real boat holiday between the islands. We had a lot of laughs. The cuisine is excellent and rich, I already miss it. It was a week that, due to the richness of the moments lived, leaves the feeling of a much greater time spent. Even on land, Sergio and Carmen have always organized and recommended very fun, interesting and exciting activities. Thank you Sergio and thank you Carmen !!

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!

Guides & tips


Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
uide to sailing vacations with children

Aeolian Islands: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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