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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!

ENJOY: in the blue painted blue of the Aeolian Islands

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€690

€529

Per person

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4.9

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

4 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

5 departures available

September - November

€583

Per person

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4.8

Sail to the Aeolian Islands with an experienced crew on a catamaran!

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

September

Starting from

€950

€760

Per person - min 2 pax

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5.0

Super!

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

Italy: Aeolian Islands

7 days - 7 nights

One departure available

September

€583

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - November

Starting from

€650

€585

Per person

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4.9

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

Italy: Aeolian Islands

6 days - 7 nights

2 departures available

August - September

Starting from

€870

Per person

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4.9

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

One departure available

August - September

€900

Per person

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4.9

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

4 departures available

September - October

€800

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

8 departures available

September - November

Starting from

€475

€451

Per person

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4.8

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

Italy: Aeolian Islands

5 days - 4 nights

4 departures available

September - October

€590

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

5 departures available

August - October

Starting from

€1,450

€943

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

412 reviews

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Different Flotilla: Party and new friends in the Aeolian Islands

08/30/2025

Marco T.

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Italy

Excellent organization, comfortable catamaran. The boat life is beautiful.
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Different Flotilla: Party and new friends in the Aeolian Islands

08/30/2025

Francesca R.

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Italy

My experience was perfect from every point of view. The group was incredible, so congratulations to those who chose the pairings of our Nereo catamaran!! Top skippers, nice, prepared, helpful and perfectly in line with the group!
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Different Flotilla: Party and new friends in the Aeolian Islands

08/30/2025

Cristian M.

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Italy

Fantastic holiday and experience for those who want to approach the world of sailing. Skipper Bruno and co-skipper Cinzia were really super both in terms of management and company. As ideas for improvement for the Aeolian tour, I would say that we could increase the moments of going ashore to visit the islands more.
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Different Flotilla: Party and new friends in the Aeolian Islands

08/30/2025

Sailor

Awesome experience... wonderful places.. Perfect organization and fantastic group! Roberto and Niccolò are the skippers that everyone would like for their professionalism, kindness and sympathy

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