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Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

experiences

4.9

Super!

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

21 departures available

May - October

Starting from

€950

Per person

4.8

Super!

Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

Italy: Northern Sardinia

6 days - 7 nights

14 departures available

June - September

Starting from

€625

Per person

4.8

Super!

Let's discover the Aeolian Islands together by sailing

Italy: Aeolian Islands

7 days - 7 nights

24 departures available

May - October

Starting from

€600

Per person

4.6

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

Italy: Northern Sardinia

6 days - 7 nights

19 departures available

May - October

Starting from

€600

€540

Per person

4.9

Super!

"Nel blu dipinto di blu" - Sailing cruise in Northern Corsica

Italy: Tuscany

7 days - 7 nights

10 departures available

June - September

Starting from

€680

Per person

4.9

Super!

Gulf of Poets and Cinque Terre

Italy: Liguria

2 days - 2 nights

One departure available

June

€360

Per person

4.9

Super!

Long weekend among the queens of the archipelago - Elba and Capraia

Italy: Tuscany

4 days - 3 nights

16 departures available

May - September

Starting from

€430

€409

Per person

5.0

Super!

In the Aeolian Islands with chef on board

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July

€1,000

Per person

4.8

Super!

Pontine Blue - Midweek Escape

Italy: Pontine Islands

4 days - 3 nights

17 departures available

April - July

Starting from

€210

Per person

4.9

Super!

On holiday with Dad to discover Elba and Capraia

Italy: Tuscany

5 days - 5 nights

4 departures available

June - September

€350

Per person

5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

6 departures available

June - September

Starting from

€800

€720

Per person

4.9

Super!

Life-changing experiences: Four days in the Pontine Islands with photographer on board

Italy: Pontine Islands

4 days - 3 nights

12 departures available

June - September

Starting from

€450

€428

Per person

Why book a holiday with Sailsquare?

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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.

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

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Private yacht sailing holidays with skipper in Italy

2590 reviews

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

11/5/2025

Marco F.

Switzerland

Matteo is a professional skipper and above all a pleasant person, who steers the boat and situations with lightness and experience. Luke [hidden] a well-maintained and decidedly comfortable and spacious boat. Nice opportunity and fantastic company / crew, not to be forgotten and to be seen again with pleasure in a next navigation, between sea aperitifs and laughter.

LET'S GO TO TOTANI - Festival in Capria

11/5/2025

Marco D.

Italy

Unforgettable and fun experience, very prepared skipper who tamed a sea that was not exactly docile. The fishing competition is beautiful and suggestive.

End of season weekend in the Aeolian Islands

11/3/2025

Collwyn Y.

Italy

I come from the North Sea but I now live the Italian Alps and I’ve been really missing the ocean. So, after much thinking, I decided to treat myself to a little sailing holiday in October. [hidden] (the boat) is cozy yet has every comfort and the hosts really make you feel like you’re being treated to an Italian family gateway. Giacomo and Laura go above and beyond to fit everyone's need and requests. They exceeded my expectations! Great company, great food and insane landscapes! Nothing quite like sleeping under the stars, lulled by the gentle rocking of the boat. Thank you, I hope next time I can bring my family from Scotland!

End of season weekend in the Aeolian Islands

11/3/2025

Gaia R.

Italy

Honestly, I had underestimated a sailing holiday in Sicily in October but instead it was unforgettable. The Aeolian Islands are even more beautiful in this period, being less crowded. Living them from the sea, guided by two local people, then, becomes a truly authentic experience! Thank you Giacomo and Thank you Laura, we will definitely be back this summer to be able to have even more fun with the longer 🌬️ days

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