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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.

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5.0

Super!

Barcolana Weekend: experience the largest regatta in the world

Italy: Venice and the Gulf of Trieste

3 days - 2 nights

One departure available

October

€420

Per person

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5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

29 departures available

October - November

€150

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

4 departures available

October - November

€350

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

One departure available

October

€750

€675

Per person

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4.8

Super!

Experience the sea in October!

Italy: Tuscany

2 days - 2 nights

3 departures available

October

€200

Per person

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New

Cruise between the Maddalena archipelago and South Corsica

Italy: Northern Sardinia

7 days - 7 nights

One departure available

October

€585

Per person

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4.7

Squid Regatta

Italy: Tuscany

2 days - 2 nights

One departure available

October

€180

Per person

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5.0

It's time for sun and sea!

Italy: Liguria

2 days - 1 night

2 departures available

October

€320

Per person

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4.1

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

38 departures available

January - December

Starting from

€275

€248

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

October

€740

Per person

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5.0

Sailing, swimming and aperitif at sunset ... What else?

Italy: Lake Garda

1 day - 0 nights

5 departures available

October

Starting from

€59

Per person

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4.6

Relaxing weekend and sailing school

Italy: Tuscany

2 days - 1 night

One departure available

October

€220

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

3632 reviews

Aeolian Islands: between sea and authentic flavours

10/5/2026

Giorgia P.

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IT

Wonderful experience!! Well maintained boat; very comfortable to have a bathroom available in each cabin. The tour allowed us to visit enchanting places, swim in crystal clear waters and enjoy excellent fish dishes and exquisite desserts. Carlo, our skipper (Merchant Marine Officer) has put his skills and abilities at our disposal. End of September was a good choice, always sunny without ever sultriness, the right water temperature for wonderful baths. Happy and fun company, with Lorenzo I was able to share culinary secrets in the kitchen. With a bit of luck, we sailed for a stretch in the company of a pod of dolphins. A holiday to be repeated and recommended. Giorgia P.
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

10/5/2026

Michelle B.

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US

Mossimo and Valentina were superb! Incredible sailing, delicious food, taking us to stunning locations it far exceeded my expectations! I highly recommend sailing with them. Cheers! Michelle

Egadi paradise for sailing and snorkeling

10/4/2026

Luzia K.

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DE

Unfortunately, a wonderful week has come to an end. Mario is a great skipper and host. I can't even list all the bays where we swam in the crystal clear water. Gaia took very good care of us. Nice people, sun, absolutely relaxed.
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Aeolian Islands in a big and new catamaran: sea, sun, relaxation

10/4/2026

Loredana T.

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IT

A simply wonderful week, made even more special by the skipper who accompanied us and his beautiful catamaran. Maurizio is a very kind, respectful person, he is very helpful. He was able to create a beautiful balance between professionalism and conviviality, making us always feel at ease and allowing us to experience the sea with lightness and serenity. I couldn't have had a better skipper. Thank you for this wonderful week ❤️⛵️

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