header cover
sailsquare logo

Private yacht sailing holidays with skipper in the Aeolian Islands

Discover the magic of sailing holidays in the Aeolian Islands! Hire a whole boat: a new way of traveling with your loved one, your friends or your family. Find your dream adventure among thousands of holidays from the Mediterranean to the Caribbeans.

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

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

cover image
avatar image

4.9

Super!

An Aeolian adventure: sailing, nature and relaxation in the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

June - August

Starting from

€750

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 - Private yacht sailing holidays with skipper in the Aeolian Islands

250 reviews

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!
avatar placeholder

Sea, sailing and relaxation in the beautiful Aeolian archipelago

05/4/2025

Alexia D.

-

France

Super séjour avec Antonino ! Il est très sympa, à notre écoute et très arrangeant ! On a visité les îles de Vulcano, Salina et Panarea. Le rythme était adapté à nous : on a bien pu profiter du voilier et des îles sur lesquelles on a randonné et/ou on s'est promené. Le voilier est très fonctionnel,nous avons cuisiné à bord certains jours. On s'est senti comme à la maison et avons partagé de bons moments avec Antonino. Une superbe façon de voyager : on recommande vivement !

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!

-

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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