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Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

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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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5.0

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

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

€690

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

One departure available

September

€950

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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4.9

Super!

Four days in the Aeolian Islands from Capo D'Orlando

Italy: Aeolian Islands

4 days - 4 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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4.9

Relaxing weekend in the Aeolian Islands: Lipari, Vulcano and Salina

Italy: Aeolian Islands

3 days - 2 nights

7 departures available

September - October

€320

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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4.8

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€700

€630

Per person

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4.5

Sailing holiday with maximum comfort

Italy: Aeolian Islands

6 days - 7 nights

One departure available

September

€700

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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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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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.

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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 - Yacht sailing holidays & skippered tours in Italy

2250 reviews

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

09/8/2026

Stefania P.

A week on a catamaran in the Aeolian Islands that I will hardly forget! ⛵️🌊 Andrea, our skipper, and Arianna, our hostess, were just amazing. Andrea is a real guarantee: competent, quiet and solid, he knows the Aeolian Islands and their sea like the back of his hand. He took us to discover wonderful places making us feel always in excellent hands. Arianna was very attentive to everything and everyone, always present and available. It was enough for someone to pronounce the word "beer?" and Arianna had already uncorked and made cheese, olives and taralli appear. They definitely spoiled us even at the table: delicious fish, pasta, vegetables, salads, wine... We really didn't miss anything. We discovered the Aeolian Islands from a wonderful perspective: during the day from the sea, between bays, dives and incredible views, and in the evening going ashore for a walk, a granita or an aperitif. One of the moments that I will definitely take with me is Stromboli: the sea crossing at sunset and the spectacle of the Sciara del Fuoco seen from the catamaran were exciting and evocative, difficult to describe in words. To make this holiday even more special was also the group I was lucky enough to find. People who a week earlier were strangers and with whom, between laughter, life on a boat, aperitifs and shared moments, a beautiful understanding was created. I left for a week in the Aeolian Islands and came back with many more memories than I thought I would pack. ❤️ Thank you Andrea, Arianna and the whole group for making this experience so special. I would do it again tomorrow! Greetings from Paris 😉
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Aeolian Islands on a catamaran, professional skipper/hostess, what else?

09/8/2026

Rosita L.

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IT

Much more than just a holiday! An unforgettable experience where nothing is left to chance. Everything bordered on perfection, from the itinerary to the food (impeccable raw material and preparation, restaurant-like, if not better!), from the moments on board to those on land. Andrea is an expert navigator and a great connoisseur of the area, you can only trust him and rely on him to spend a dream week. To make everything even more relaxing the constant care of Arianna, the hostess, a discreet presence and attentive to everything, from morning to evening! Also unexpected was the wonderful group of people with whom I was lucky enough to share the experience. In short, expectations were very high and all were abundantly exceeded!
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Comfortably Aeolian Islands: Catamaran Cruise with Steward

09/7/2026

Barbara R.

-

IT

Days of pure relaxation, the skipper Giorgio and the cook Diego made us spend a fantastic week, pampering us and making us discover the wonders of these islands. Thanks guys!

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

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Sardinia

Costa Smeralda, Maddalena Archipelago and San Pietro Island are just some of the best destinations for a sailing or catamaran holiday in Sardinia.
Guide to the Sardinia on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
Guide to sailing vacations with children

Italy: the most beautiful places to sail

Tuscany (32)Pontine Islands (19)Aeolian Islands (15)Liguria (14)Aegadian islands (9)Northern Sardinia (8)Naples & Amalfi Coast (5)Sicily (4)Southern Sardinia (4)Lake Garda (3)

Italy: departures by month

october (52)november (4)december (1)january (1)february (1)march (1)april (3)may (4)june (5)july (5)

Other travel ideas

Sailboat (168)Whole boat with skipper (144)Cooking service onboard (67)Catamaran (51)All inclusive (38)Exotic destinations (20)Courses & regatta (16)Sport & wellness (11)Offshore (10)Day trips (7)

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