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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

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Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

7 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

5 days - 4 nights

3 departures available

September

€490

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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4.8

Super!

COUS COUS FEST: Un Week End di Mare, Vela, Cous Cous e Musica!

Italy: Sicily

4 days - 3 nights

2 departures available

September

€345

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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4.9

Super!

A weekend on the most beautiful island of the Tyrrhenian Sea - Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

September

€280

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!

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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4.8

Super!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

One departure available

September

€1,100

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

2 departures available

September

€950

Per person

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4.8

Super!

Elba, Tuscan archipelago or Corsica aboard a full opt catamaran.

Italy: Tuscany

7 days - 7 nights

3 departures available

September

Starting from

€850

Per person

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4.8

Super!

Cous Cous Festival tra le Egadi e San Vito Lo Capo in Catamarano

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€850

Per person

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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

14900 reviews

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Gulf of Poets

09/2/2026

Caterina G.

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IT

The itinerary is quite limited (thanks in our case also to the rough sea), so it can certainly be a good first experience on a sailing boat to experience life on board, but you should not expect to sail too much or see many different places. Price in my opinion a bit high for the proposed tour. Giovanni is however very nice, kind and helpful. Very nice and comfortable boat. Overall pleasant experience, but I don't think I would do it again.

Sardinia and Strait of Bonifacio on a 50-foot sailboat

09/2/2026

Huseyin G.

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TR

I joined the trip as a solo traveler and it was a lovely week on boat with our captain Gianluca and Italian company. The bays and coves we visited were just fantastic. This was my third time in Northern Sardinia and I just can’t get enough of it. For the first time I have seen the Corsica side (only the south, around Bonifacio) and the beaches there were equally amazing. I especially loved the lagoon between Piantarella beach and Ile Piana. You can literally walk from the beach to the nearby island in one of the most crystal clear turquoise water you can find. The planning in advance was great. The experience of our captain was clear, we did the shopping the first evening we all came together and we were ready the sail first thing in the morning. I was also lucky enough to have great Italian company who helped significantly with cooking. Thanks again, il capitano, Gianluca, and everyone else. I already look forward to my next Sardinia trip.
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Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

09/2/2026

Gloria R.

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IT

The Egadi islands are truly a paradise for those who love the sea, characterized by a largely unspoiled nature and a seabed still rich in fish and flora. The long swims we took in the wonderful coves of Favignana and Levanzo, also thanks to an extremely favorable weather and a very warm sea, we will hardly forget them. Unfortunately, I cannot say the same about the management and comfort on board, which, for the first time in over 10 years of sailing holidays, did not fully meet my and my husband's expectations and indeed risked compromising the success of the entire holiday. The most painful note concerned life on board, on this aspect I am sorry to deviate from the numerous positive reviews I have read and for which we had chosen to have this experience on a boat in the Egadi Islands with this skipper: the atmosphere on board was very rigid (at times even very quarrelsome with another crew member) and therefore heavily conditioned our freedom of movement and expression. The crew was treated only as guests, without any possibility of participating in the maneuvers or in the conduct of the same and without being able to receive convincing explanations on the change in the navigation program. The comfort of the boat was also penalized for some choices that created considerable inconvenience: - The tender, positioned on the bow and never used, effectively prevented the use of the only sunbathing space and blocked the porthole, making the forward cabins very hot due to lack of adequate ventilation. - The foam mattresses, without the stop to keep them together to be able to access the gullies below, separated continuously during the night, making rest extremely difficult. I hope that this feedback can be a useful starting point to improve the comfort and experience of the next crews who wish to visit the paradise of the Egadi Islands, which really deserve to be visited and experienced in total relaxation and harmony.
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Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

09/2/2026

Giulio M.

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IT

Really great boat experience! A special thanks to Giacomo, our skipper, who despite his young age proved to be extremely professional, prepared and attentive at all times. A skill that is anything but obvious, which has allowed us to live the week in total tranquility and safety. The mood of the holiday is also beautiful: pleasant, relaxed and well balanced, with the right mix of fun, relaxation and conviviality. An experience that I absolutely recommend and that I would gladly do again!

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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 (38)Aeolian Islands (20)Pontine Islands (19)Liguria (17)Aegadian islands (13)Naples & Amalfi Coast (10)Northern Sardinia (9)Sicily (4)Southern Sardinia (4)Lake Garda (3)

Italy: departures by month

october (50)november (4)december (1)january (1)february (1)march (1)april (3)may (4)june (5)july (4)

Other travel ideas

Sailboat (199)Whole boat with skipper (171)Cooking service onboard (74)Catamaran (55)All inclusive (40)Exotic destinations (23)Courses & regatta (15)Offshore (12)Sport & wellness (10)Day trips (7)

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