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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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5.0

Super!

We have known the Aeolian Islands for 20 years, live them with us!

Italy: Aeolian Islands

7 days - 7 nights

8 departures available

June - October

Starting from

€690

Per person

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4.9

Super!

Sailing & adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

June - October

Starting from

€700

Per person

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4.8

Super!

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

Italy: Aeolian Islands

6 days - 7 nights

5 departures available

August - September

Starting from

€583

€525

Per person

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5.0

Super!

Aeolian Islands in the name of sailing, fishing and relaxation

Italy: Aeolian Islands

3 days - 2 nights

9 departures available

June - August

Starting from

€390

€351

Per person

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4.5

Unforgettable adventure in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

13 departures available

July - November

Starting from

€540

€513

Per person

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4.8

Super!

A week of sea, volcanoes and fun in the Aeolian Islands

Italy: Aeolian Islands

7 days - 7 nights

6 departures available

July - September

Starting from

€690

€621

Per person

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4.8

Super!

From the Pontine to the Aeolian Islands - Adventure, Navigation, and Relaxation - One Way

Italy: Aeolian Islands

5 days - 6 nights

One departure available

July

€590

Per person

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4.9

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

14 departures available

July - November

Starting from

€600

€540

Per person

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5.0

Super!

Aeolian Islands: let yourself be pampered among volcanoes, sea and gourmet cuisine!

Italy: Aeolian Islands

6 days - 7 nights

8 departures available

September - October

Starting from

€800

€720

Per person

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4.8

Super!

From Lipari to Palermo: magical week on a catamaran with a hostess

Italy: Aeolian Islands

7 days - 7 nights

One departure available

August

€1,450

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

3 departures available

September

€945

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

9 departures available

June - October

Starting from

€640

€480

Per person

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Reviews - Yacht sailing holidays & skippered tours in the Aeolian Islands

2032 reviews

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

06/22/2026

Valeria T.

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IT

Beautiful week together with Emanuele (skipper) and Daniele (steward). Highly recommended.
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We have known the Aeolian Islands for 20 years, live them with us!

06/22/2026

Massimo B.

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IT

Fantastic experience with Sailsquare in the Aeolian Islands. The real added value of the holiday was our skipper, Pasquale. He didn't just take us to sea, but guided us step by step in the world of sailing and to discover each island, telling us many local anecdotes and stories. Pasquale knows all the fishermen and local characters perfectly, which made us live an authentic experience and outside the classic tourist circuits. His advice was not limited to the sea: he also personally guided us on shore excursions, such as on Vulcano and Stromboli.Special note of merit for the cuisine: we enjoyed excellent lunches on board with fresh fish, bought directly from the fishermen and cooked on the spot. Highly recommended!

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

06/21/2026

Barbara M.

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IT

We spent a super holiday visiting all the Aeolian Islands, captain Emanuele and skipper Daniele despite their young age were very professional, they delighted us with excellent menus always based on fish and sashimi and what can I say.... Aperitifs, wine, beer and gin galore. The catamaran very comfortable, well maintained and always clean. We hope to be able to take another holiday with them again! Guys keep it up!! 😘
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We have known the Aeolian Islands for 20 years, live them with us!

06/21/2026

Anna M.

-

IT

A week in the Aeolian Islands that went far beyond a simple holiday. An authentic experience made of crystal clear sea, breathtaking sunsets, good food and special people. A heartfelt thank you to Pasquale, an exceptional skipper, always available, empathetic and able to put everyone at ease from the first moment. His sympathy and deep knowledge of the Aeolian Islands allowed us to experience the islands in the truest way, discovering enchanting bays, hidden corners and local traditions. Life on the boat made everything even more magical: sharing this adventure with people met on board, who in a few days became travel and laughter companions, was one of the most beautiful aspects of the experience. I return home with my heart full of memories, emotions and new friendships. A trip that I recommend to anyone at least once in their life and that, without a doubt, I will repeat. The Aeolian Islands seen from the sea have something special that remains inside. 💙

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