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Sailboat yacht sailing holidays & tours in Italy

Discover more than 96 opportunities to get on board a Sailboat adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

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5.0

Super!

Weekend at the Pontine Islands

Italy: Pontine Islands

3 days - 2 nights

6 departures available

September - October

Starting from

€337

Per person

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4.8

Super!

Let's discover the Aeolian Islands together in Vela

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€690

Per person

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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

4 departures available

October - November

€583

Per person

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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

One departure available

September

€689

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

6 departures available

September - October

Starting from

€337

Per person

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4.7

Weekend a Capraia, trekking e natura

Italy: Tuscany

3 days - 2 nights

3 departures available

October

€200

Per person

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4.7

COUS COUS FEST: A Weekend of Sea, Sailing, Cous Cous and Music!

Italy: Sicily

4 days - 3 nights

2 departures available

September

Starting from

€390

€351

Per person

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4.8

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

14 departures available

March - October

Starting from

€200

€180

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

4 departures available

September - October

Starting from

€220

Per person

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4.7

Lampedusa, Linosa and Lampione, islands on the high seas

Italy: Pantelleria and Lampedusa

6 days - 7 nights

One departure available

September - October

€850

Per person

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4.9

Super!

Traveling and dreaming in the Gulf of Poets - All Inclusive

Italy: Liguria

2 days - 1 night

2 departures available

September

€260

Per person

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4.8

Super!

Introductory sailing course

Italy: Liguria

2 days - 1 night

One departure available

September

€260

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 - Sailboat yacht sailing holidays & tours in Italy

12542 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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