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Yacht sailing holidays & skippered tours in Italy

Discover more than 83 sailing holidays in Italy. Book a spot onboard and live 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

One departure available

September

Starting from

€337

Per person

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5.0

Super!

Midweek relaxing in the Pontine Islands

Italy: Pontine Islands

4 days - 3 nights

3 departures available

September - October

Starting from

€337

Per person

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4.9

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

One departure available

September - October

€950

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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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

One departure available

September

€441

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

September

Starting from

€220

Per person

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4.9

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

September

Starting from

€200

€180

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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4.7

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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4.9

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

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4.8

Super!

Day trip with aperitif at sunset!

Italy: Liguria

1 day - 0 nights

One departure available

September

€65

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

13591 reviews

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Midweek relaxing in the Pontine Islands

09/13/2025

Alessandra S.

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Italy

Despite the not exactly nice weather, it was a holiday to remember for the beauty of the coves, gentle even in the absence of sun, for the baths and SUP excursions, for the wonderful Pontine islands, seen from several perspectives from the sea and visited on foot when possible, rich in history and energy, for the spot-on company from all over Italy and...... especially for Mirko, the perfect skipper. Tireless, patient, helpful, proactive, reassuring and, to great surprise, an expert cook. Never on alert, it instills constant security in the crew. Congratulations to the organization, to us, who worked as a team, and to Mirko, our favorite skipper. 🥰
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The Egadi Islands as you've never seen them on a 16-meter boat

09/13/2025

Rosario P.

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Italy

Unforgettable holiday
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4 days in the Pontine Islands (sailing school)

09/13/2025

Erica M.

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Italy

great experience, our skipper Michele turned out to be very professional, attentive and extremely helpful. Although the weather was not the best, he did everything to make this holiday unforgettable. The boat is very well maintained, it is clean and tidy. Even my 13 year old daughter who was at her first experience came back very satisfied and happy. A big thank you also to our group with whom we shared 4 days superr!
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4 days in the Pontine Islands (sailing school)

09/13/2025

Chiara C.

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Italy

I have just spent four unforgettable days sailing between the Pontine Islands with skipper Michele, and I can only share an overwhelming enthusiasm for this experience! Although time was not always on our side, Michele demonstrated an uncommon competence and passion, guiding us with mastery through the wonders of this archipelago. His ability to handle the boat and find the best spots allowed us to enjoy every moment, even when the weather tried to throw a spanner in the works. The Pontine Islands are a true paradise: crystal clear waters, hidden coves and breathtaking landscapes that make you forget everything else. The boat was comfortable, well maintained and perfect for this adventure, with cozy spaces that made us feel at home. The company on board? Simply fantastic! Laughter, chats and shared moments that made the trip even more special. But the real highlight? Dolphin encounters! Not one, but several magical moments in which these beautiful animals accompanied us, swimming next to the boat for a time that seemed endless. It was exciting, an experience that I will carry in my heart forever. Michele is not only an experienced skipper, but also a person who knows how to convey love for the sea and for these islands. I highly recommend this trip to anyone who wants to experience the sea in an authentic way, between nature, relaxation and unforgettable moments. Thank you, Michele, for making these four days a daydream! Definitely!

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