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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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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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4.8

Super!

All-Inclusive Sailing: Capri, Positano, Amalfi

Italy: Naples & Amalfi Coast

3 days - 2 nights

One departure available

September

€790

Per person

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5.0

Super!

Barcolana 58: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€280

Per person

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4.8

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€700

Per person

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4.8

Super!

Midweek weekend in Elba: sea, scents, colors

Italy: Tuscany

2 days - 2 nights

2 departures available

September

€200

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

4 departures available

September - October

Starting from

€230

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

4 days - 4 nights

2 departures available

September

Starting from

€490

€440

Per person

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5.0

Super!

Giglio or Elba the pearls of the Tuscan archipelago

Italy: Tuscany

2 days - 2 nights

3 departures available

October - November

€250

Per person

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5.0

New

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

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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4.7

Voices of the Pelagos: artistic-scientific whale watching expedition with WWF guide

Italy: Tuscany

4 days - 4 nights

One departure available

October

€453

Per person

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4.8

Super!

Five days barefoot between Tuscany and Corsica

Italy: Tuscany

5 days - 4 nights

One departure available

September

€490

€440

Per person

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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

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

14980 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 😉

Gulf of Poets

09/8/2026

Silvia R.

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IT

The skipper Giovanni welcomed us on board impeccably. He was courteous, helpful and involved us in the different moments of life on the boat. The view of the Gulf was much appreciated but the short journeys do not allow you to take full advantage of the sail (even if Giovanni promptly organized sailings).
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Capri, Ischia and Amalfi Coast by catamaran with hostess and cook

09/8/2026

Valentina A.

-

IT

We really enjoyed our time. The boat was brand new and super spacious, with very large rooms. Air conditioning, especially during such a hot summer, was really essential. The skipper Alessio was always very kind and willing to meet our needs, as well as the two girls of the crew, who took care of the cleaning, the kitchen and also the maneuvers. The food was also great and having someone take care of the galley, cooking and cleaning is a luxury that really makes a difference on a boat. We liked the Amalfi Coast, even if honestly it did not particularly excite us. In our opinion, this type of holiday could be enhanced even more by itineraries such as Sardinia or Greece, which we also know from experience. The only advice I would give to Alessio is to provide a briefing with the basic information before departure, especially to help those who have never taken a boat holiday. For the rest, really positive experience!

Weekend in the Pontine Islands

09/8/2026

Alessandro Z.

-

IT

Fabio is a precise, attentive, helpful skipper and puts you at ease. Really a nice experience.

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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 (16)Liguria (14)Aegadian islands (9)Northern Sardinia (8)Naples & Amalfi Coast (5)Southern Sardinia (4)Sicily (4)Lake Garda (3)

Italy: departures by month

october (53)november (4)december (1)january (1)february (1)march (1)april (3)may (4)june (5)july (5)

Other travel ideas

Sailboat (169)Whole boat with skipper (145)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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