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Sailboat yacht sailing holidays & tours in Aeolian Islands

Discover more than 11 opportunities to get on board a Sailboat adventure in Aeolian Islands. A unique experience with a local skipper, starting at €350 a week.

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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

18 departures available

May - October

Starting from

€689

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

One departure available

October - November

€583

Per person

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4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

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

One departure available

October - November

€475

Per person

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3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

2 departures available

October - November

€600

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

15 departures available

July - October

Starting from

€590

Per person

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4.6

Aeolian Islands: wellness, taste, fun with fabulous cook on board

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

July - August

Starting from

€910

€865

Per person - min 2 pax

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5.0

EOLIE IN RELAX - Boat with 3 cabins and 3 bathrooms

Italy: Aeolian Islands

6 days - 7 nights

One departure available

October - November

€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

15 departures available

April - October

Starting from

€400

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

Per person

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5.0

We circumnavigate the Aeolian Islands starting from Vulcano

Italy: Aeolian Islands

6 days - 6 nights

One departure available

October

€550

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 - Sailboat yacht sailing holidays & tours in Aeolian Islands

1815 reviews

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Let's discover the Aeolian Islands together by sailing

09/28/2025

Alessandro N.

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Italy

Very positive experiences, well organized and well managed. Amazing location
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Between seas and volcanoes, fall in love with the Aeolian Islands

09/22/2025

Pierluigi O.

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Italy

Very nice and prepared skipper, super boat, itinerary studied in detail. Unique holiday
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A week in the Aeolian Islands - 6 islands in seven days

09/22/2025

Sergio V.

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Italy

Nicola cares a lot about the satisfaction of the crew to whom he dedicates all his attention and time. He cares, assists and bends over backwards for all aspects: itinerary, life on board and offboard. Sailing competence and safety at sea. Highly recommended!
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We have known the Aeolian Islands for 20 years, live them with us!

09/22/2025

Amalia G.

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Italy

A perfect week in the Aeolian Islands, thank you Pasquale for introducing us to these wonders!

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