header cover
sailsquare logo

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.

cover image
avatar image

5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

June - September

Starting from

€935

€748

Per person

cover image
avatar image

4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

June - November

Starting from

€530

€477

Per person

cover image
avatar image

5.0

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

June - November

Starting from

€650

€585

Per person

cover image
avatar image

5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

12 departures available

June - September

Starting from

€689

Per person

cover image
avatar image

5.0

Between seas and volcanoes, fall in love with the Aeolian Islands

Italy: Aeolian Islands

5 days - 4 nights

11 departures available

July - October

€590

Per person

cover image
avatar image

4.8

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

June - August

Starting from

€2,062

€1,340

Per person

cover image
avatar image

4.8

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

16 departures available

June - October

Starting from

€530

€504

Per person

cover image
avatar image

4.8

Magical Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - September

Starting from

€640

Per person

cover image
avatar image

4.8

Super!

Discovering the Aeolian Islands Between Nature, Relaxation and Fun

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€745

€671

Per person

cover image
avatar image

4.8

Enjoy: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 6 nights

9 departures available

June - October

Starting from

€530

€504

Per person

cover image
avatar image

4.8

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - August

Starting from

€910

€774

Per person - min 2 pax

cover image
avatar image

4.9

Super!

Aeolian Islands by catamaran, professional skipper/hostess, what else?

Italy: Aeolian Islands

6 days - 7 nights

4 departures available

August - September

Starting from

€870

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

1752 reviews

avatar placeholder

We have known the Aeolian Islands for 20 years, live them with us!

06/9/2025

Alice M.

-

Italy

Settimana alle Eolie con Pasquale: vela, aperitivi e “bagni di sale” . Abbiamo trascorso una settimana in barca a vela alle Isole Eolie con Pasquale, e l’esperienza è stata tanto rilassante quanto divertente. Eravamo solo in tre a bordo, il che ha reso il viaggio intimo, personale e davvero “su misura”. Indimenticabili il tramonto su Vulcano e la spettacolare sciara di fuoco dello Stromboli che abbiamo potuto ammirare in silenzio. Pasquale è un navigatore esperto e appassionato capace di guidarci con discrezione e competenza verso angoli nascosti e affascinanti. A bordo la convivenza è stata semplice e naturale: libere di goderci la barca, partecipare alla navigazione se volevamo, o semplicemente oziare tra un bagno e un aperitivo. Ognuno ha fatto la sua parte, tra cucina e pulizie, con leggerezza e spirito collaborativo e di condivisione. Sicuramente un viaggio da consigliare a chi ricerca un’esperienza di mare autentica! PS: Un abbraccio speciale al nostro compagno di bordo Pietro — esperto di mare e, soprattutto, di vita! — Alice & Alessandra
avatar image

Long weekend exploring the Aeolian Islands

06/5/2025

marc P.

-

Canada

Nous avons pris le forfait 3 nuits-4 jours dans les îles éoliennes, sur le beau voilier de Mario et nous avons adoré l'expérience. Malgré les différences de langue (français, anglais et italien), nous avons très bien su nous comprendre..Mario est patient et fait des efforts pour bien communiquer Mario a su nous accueillir et nous aider a s' installer a bord. Mario nous a fait découvrir les îles et nous a amener dans de superbes criques . On a participer à l'élaboration du trajet , selon nos goûts et nos attentes.. Toujours souriant , Mario nous fait découvrir sa passion et son experience pour la voile ( malheureusement pas beaucoup de vent lors de notre voyage🫤) Mais quand même sorti les voiles quelques fois. Quelle belle expérience ..je recommande a 100%...avec Mario, !!
avatar image

Long weekend exploring the Aeolian Islands

06/4/2025

Diane L.

-

France

Superbe croisière sur le bateau de Mario ! Nous avons passé un séjour hors du temps entre les îles éoliennes. Il nous apprend aussi bien la voile que l'italien ! Je recommande fortement ce séjour à bord du beau bâteau de Mario.
avatar placeholder

Sea, sailing and relaxation in the beautiful Aeolian archipelago

06/4/2025

Deborah R.

-

United States

We had a wonderful time! Captain Antonino showed us the beauty and majesty of the Aeolian Islands even better than we could’ve imagined. Our hostess Claudia spoiled us with delicious food at every meal. The trip was truly beyond expectations!

Customer Support

nightLifeGeneralInfo

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!

search

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