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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.

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4.5

Sailing holiday with maximum comfort

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

September

€700

Per person

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

9 departures available

August - October

Starting from

€607

Per person

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4.8

Sailing and Trekking in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€730

Per person

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4.7

Sailing to Sicily: 4 days of sea, comfort and adventure

Italy: Aeolian Islands

4 days - 4 nights

One departure available

August

€375

Per person

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5.0

3 days in the wild Aeolian Islands - All inclusive & flexible dates

Italy: Aeolian Islands

2 days - 2 nights

5 departures available

August - September

Starting from

€723

€650

Per person

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5.0

Aeolian Islands on a sailing boat: a tailor-made holiday with an exclusive boat

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

August - September

Starting from

€800

Per person

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4.6

Aeolian Islands: well-being, taste and fun

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

August - September

Starting from

€690

Per person - min 2 pax

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Aeolian Islands by sailboat: 6 days between volcanoes and clear waters

Italy: Aeolian Islands

6 days - 6 nights

One departure available

August

€6,950

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€950

Per person

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4.9

Aeolian Islands on a luxury sailing boat

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€700

Per person

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4.2

Authentic Aeolian Islands on a sailboat: between local flavors and crystal clear sea

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€700

€620

Per person

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Aeolian Week

Italy: Aeolian Islands

7 days - 6 nights

5 departures available

August - September

Starting from

€750

Per person

Why book a holiday with Sailsquare?

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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

2083 reviews

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Aeolian Islands with hostess/cook BOAT 16.5 mt exclusive x6 people

08/4/2026

chiara s.

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IT

The holiday you need! Spectacular landscapes, wonderful people, amazing cuisine! All surrounded by water, sun and wind! Congratulations on the passion and love you have for the boat, the kitchen and the life you live! You can feel everything! Unforgettable moments!
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Comfortably Aeolian Islands: Catamaran Cruise with Steward

08/3/2026

Bolina S.

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FR

Magnificent crew, helpful, attentive, smiling, competent, efficient, superb landscapes and unforgettable villages, unforgettable memories, thank you for any top catamaran
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Aeolian Islands with hostess/cook BOAT 16.5 mt exclusive x6 people

08/3/2026

Stefania Q.

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IT

The trip with Marco and Valentina on [hidden] is a real journey experiencing the sailboat. They have an attitude of openness and availability given, in addition to professionalism and experience, by the desire to convey their love for the sea in complete relaxation. With great patience they understand who gets on board and the needs of each one. Valentina cooks excellently and respecting local products. You feel good on [hidden], thank you!
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Sail to the Aeolian Islands with an experienced crew on a catamaran!

08/3/2026

Roberta D.

-

IT

One of the most beautiful cruises ever done! The skipper Andrea (together with the stewart Daniele) have really thought of the cruise in the best way to make us enjoy the Aeolian Islands. We toured the most beautiful coves, enjoyed fabulous meals (created with a moving attention to the quality of raw materials) on a very comfortable cat and real attention to the wishes of the guests. In short, I would leave tomorrow (but also in an hour)! Highly recommended!

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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

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