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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!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

Per person

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5.0

Super!

We have known the Aeolian Islands for 20 years. - Live them with us.

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

October - November

€583

Per person

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4.9

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€1,450

€943

Per person

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4.5

The hidden jewels of the Aeolian Islands sailing from Palermo

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

September - November

Starting from

€475

€451

Per person

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4.9

Aeolian Islands - Large and new catamaran equipped with every comfort

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€1,030

€927

Per person

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3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

6 departures available

September - November

Starting from

€600

Per person

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4.1

Conquering the Aeolian Islands - Cook on board

Italy: Aeolian Islands

6 days - 7 nights

3 departures available

September - October

Starting from

€625

Per person

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4.9

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

Italy: Aeolian Islands

5 days - 4 nights

3 departures available

September - October

€590

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

6 departures available

September - November

Starting from

€433

Per person

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5.0

Sea, sailing and relaxation in the beautiful Aeolian archipelago

Italy: Aeolian Islands

4 days - 4 nights

4 departures available

September - October

€600

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

November

€650

€585

Per person

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5.0

We circumnavigate the Aeolian Islands starting from Vulcano

Italy: Aeolian Islands

6 days - 6 nights

4 departures available

September - October

Starting from

€550

Per person

Why book a holiday with Sailsquare?

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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

455 reviews

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

09/15/2025

Ilaria I.

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Italy

Top experience! Nicola, the skipper, is nice and super reliable, he took us to magnificent places, he was understanding to put up with us all, always available even with the kitchen, but never intrusive, and proposed an itinerary based on the weather that allowed us to see 6 islands, and allowing those who wanted to disembark on land and take turns in the village, or stay on the boat for those who, like me, prefer to enjoy the beauty of the roadstead. Very beautiful and spacious boat, as much as a sailboat can be, equipped with many small modernity and comforts. Even the group that was created with the other participants was beautiful and cohesive, leaving everyone their own freedoms. The journey to reach the Aeolian Islands and to return, starting from Livorno, was not the easiest and most direct, but it was really worth it, so don't be discouraged but leave and choose Nicola, a man of the sea and experience, and you will feel "safe". What to add if not one I hope "see you soon!" Thank you Nicola and your [hidden]!
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Aeolian Islands by catamaran, professional skipper/hostess, what else?

09/14/2025

Alessandro M.

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Italy

This is not a review but an invitation to participate in this fantastic adventure. Fabrizio is an incredible person and skipper, he knows every rock, anchorage and current of the Aeolian Islands and then cooks divinely. Arianna will pamper you, keeping the boat always clean and tidy. you will only have to think about which costume to wear! If you are lucky, like me, to find wonderful travel companions, it will be an unforgettable experience. 5 hearts, not stars!
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A week in the Aeolian Islands - 6 islands in seven days

09/14/2025

Philippe H.

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Belgium

Discovery of the Aeolian Islands with a friendly crew. Simple comfort and in line with our expectations. Cruise for lovers of the sea and extraordinary volcanic landscapes.
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Let's discover the Aeolian Islands together in Vela

09/13/2025

Antoine D.

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Canada

Very nice week aboard Mario's sailboat. The extraordinary landscapes and crystal clear water were there. Swimming every day, visiting the islands, each more charming than the next, and nights under the stars lulled to the rhythm of the waves. I recommend!

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