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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

Super!

Sailing weekend in Liguria

Italy: Liguria

2 days - 1 night

One departure available

September

€225

Per person

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5.0

Super!

Southern Sardinia on a beautiful 16m boat with a Professional Skipper

Italy: Southern Sardinia

7 days - 7 nights

4 departures available

September - October

€990

Per person

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4.8

Super!

LET'S GO TO TOTANI - Festival in Capria

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€420

Per person

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4.7

Long weekend of whale watching with a WWF guide between the Amalfi Coast, Ischia and Capri

Italy: Naples & Amalfi Coast

3 days - 3 nights

One departure available

September

€452

Per person

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4.9

Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

September - October

Starting from

€1,450

€943

Per person

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4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€300

Per person

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5.0

North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine

Italy: Northern Sardinia

6 days - 7 nights

One departure available

September

€900

Per person

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4.8

Cous cous Festival in San Vito lo Capo and the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

One departure available

September

€600

Per person

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4.8

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

One departure available

September

€360

€342

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

6 departures available

September - November

Starting from

€475

€451

Per person

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4.9

Weekend of relaxation and fun from Marina degli Aregai in Liguria

Italy: Liguria

2 days - 2 nights

2 departures available

September

€290

€275

Per person

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4.9

Aeolian Islands - Large and new catamaran equipped with every comfort

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€1,030

€927

Per person

Why book a holiday with Sailsquare?

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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 - Yacht sailing holidays & skippered tours in Italy

13617 reviews

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Midweek relaxing in the Pontine Islands

09/15/2025

Francesco M.

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Italy

The real value of this short cruise was the skipper Mirko, a seafarer of great experience, calm and pleasant company, who accompanied us with safety and fun to the most beautiful and characteristic corners of the Pontine Islands, always beautiful and that he knows deeply.
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The Wild Flotilla: dive into the wild nature of Tuscany and Corsica

09/15/2025

Giulia P.

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Italy

Four boats, two islands, a family: a few points to sum up one of the most beautiful holidays ever. Dinners at anchor under the stars, aperitifs at sunset, naps under the sun. But also coves and wild beaches, sperm whales and unexpected "wild". On board, a lot of sharing that, from the beginning, led us to bond with each other and to make us feel, right from the start, friends since always. A unique experience to experience the sea in a memorable way.
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Day trip with aperitif at sunset!

09/15/2025

Michela C.

-

Italy

For me and my daughter first experience on a sailing boat. Unfortunately the weather and the sea were not the best but thanks to Andrea, an experienced and professional skipper, it was a wonderful experience!
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Pontine Islands aboard a splendid 16-meter sailboat

09/15/2025

Giorgio R.

-

Italy

I would not recommend an experience on the Claudia boat. What was missing, first of all, was the feeling of freedom that a person seeks when choosing to sail. Leonardo is certainly a prepared skipper and very attached to his boat, but he did not seem suitable for the role of tourist skipper: he appeared too attentive to his own needs and not enough to those of his guests. From the beginning, he and his wife welcomed us with a list of prohibitions and rules, without any enthusiasm or desire to convey the joy of making us experience a beautiful holiday. They did not try to involve or create a group, and every time they set a limit or a prohibition they did so in a rigid manner, often accompanied by looks of mutual impatience that conveyed contempt rather than attention. Just a few practical examples: After each swim it was mandatory to change your swimsuit in the stern platform, preparing it in advance with a dry towel, and you could move from there only if completely dry. To smoke it was necessary to ask permission every time, and you could only do it in the stern platform/platform, and only if you "could no longer resist". At the simple request to open the awning we witnessed quarrels and screams. The passage by tender to the port of Ponza was explicitly denied despite the fact that we were at anchor in the port 50 meters from land, saying that he did not consider the idea of picking us up (without any of us having previously said he wanted to be late, otherwise it would have been understandable) and that there was a taxi boat for a fee. His wife Elena, if on the one hand cared a lot about the internal cleanliness of the boat (the bathrooms were in fact well cared for), on the other hand did not contribute to creating a relaxed atmosphere: she watched over every action done in the kitchen or below deck, rather than helping us feel at ease. What really left us stunned was the total lack of respect for the sea: several times we were asked to throw everything into the water – cigarette butts, napkins, fruit, toothpicks – and each time we refused. Such a request, from those who should love and protect the sea, we would never have expected. Although we were in an ideal context, we practically never sailed, except for about twenty minutes. To every request the answer was that there was "too much wind" or "too little wind", even when the conditions seemed favorable, there was no hurry and other boats sailed with their sails unfurled in the same direction. Finally, a very serious aspect was the failure to respect the maximum number of people on board: an extra seat was rented and I found myself sleeping in the dinette, despite having paid for a cabin. A few days earlier I had been asked to move to a bunk cabin, indicated on sailsquare as an additional 'skipper cabin', with the motivation of not creating a mixed cabin that could embarrass another guest. I had given partial availability to evaluate the spaces, being very high, and the real needs, but the management was incorrect and I felt "cheated". In reality, an additional place had been rented. To make the situation worse, Sailsquare's assistance proved to be completely insufficient and at times inquisitive. After several previous positive experiences, I wonder what is the point of relying on Sailsquare and not on other channels if, in times of real need, you do not receive any support. The Pontine Islands have very interesting scenery and a beautiful sea. The Ponzesi with whom we interacted seemed to us to be exquisite, welcoming and friendly people. Positive notes: The boat is very nice and comfortable for ten people (only the eleventh was missing a seat at the table). The management of fuel expenses was extremely correct with what was indicated and spent.

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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

Italy: departures by month

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