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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.

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€750

€675

Per person

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4.9

Super!

Three days of adventure in the Aeolian Islands

Italy: Aeolian Islands

3 days - 3 nights

One departure available

September

€400

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September - October

Starting from

€680

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€700

€630

Per person

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4.9

Aeolian Islands in a big and new catamaran: sea, sun, relaxation

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

€980

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

4 departures available

September - 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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5.0

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

Italy: Aeolian Islands

2 days - 2 nights

3 departures available

September

€723

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€945

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

2 departures available

September

€800

Per person

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4.7

Aeolian Islands: well-being, taste and fun

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September

Starting from

€690

Per person - min 2 pax

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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

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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

669 reviews

Unforgettable adventure in the Aeolian Islands

09/7/2026

Elisabetta M.

First of all, for our choice as a group too much navigation from Palermo to the islands (2 days lost) the boat needs maintenance and accessories inside (from the 4th day we no longer sailed). Elizabeth

Aeolian Islands on a luxury sailing boat

09/6/2026

isabella d.

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IT

Exactly what I was looking for....absolutely positive experience

Aeolian Islands on a luxury sailing boat

09/6/2026

Palma A.

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IT

We spent a lovely week among magical places in a comfortable boat and above all in the company of an excellent staff ! Super recommended
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A week in the Aeolian Islands - 6 islands in seven days

09/6/2026

Giorgia Z.

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IT

Unforgettable experience and wonderful places, definitely worth coming back to. A group that soon found its balance. Extremely competent and passionate skipper who involved the group in decisions, offering valuable advice based on his experience of the sea and the islands. From day one he took care that the group was balanced and that everyone participated in the daily management of the activities, an approach based on respect for the rules and common sense that is fundamental in a sailing holiday. I appreciated honesty, clarity and passion, direct communication and without formalism, which brings out authenticity and maintain a collaborative atmosphere. Qualities that on a boat are worth much more than words of circumstance. See you soon [hidden], see you soon Nik!!

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