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Sailboat yacht sailing holidays & tours in Italy

Discover more than 61 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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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

17 departures available

June - October

Starting from

€660

Per person

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4.9

Super!

Squid Festival in Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€280

Per person

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4.8

Super!

Sea, wind, sailing, fun and relaxation Tuscan Archipelago and Corsica

Italy: Tuscany

6 days - 6 nights

13 departures available

June - September

Starting from

€990

Per person

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5.0

Super!

Daily sailing trips to Ortigia and Plemmirio

Italy: Sicily

1 day - 0 nights

11 departures available

October - November

€150

Per person

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4.8

Super!

A taste of the magnificent Island of Elba

Italy: Tuscany

2 days - 2 nights

4 departures available

October - November

€300

Per person

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4.8

Super!

Barefoot holiday between Elba and Capraia on a 15m boat - 2 boats in company

Italy: Tuscany

2 days - 2 nights

One departure available

October

€230

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

7 days - 7 nights

9 departures available

June - August

Starting from

€801

Per person

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4.9

Super!

Adventure weekend in the Egadi Islands

Italy: Aegadian islands

3 days - 2 nights

One departure available

October - November

€350

Per person

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4.8

Super!

All Inclusive: Procida, Capri, Positano, Amalfi, Cetara, Sorrento

Italy: Naples & Amalfi Coast

6 days - 6 nights

4 departures available

June - August

Starting from

€1,150

Per person

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5.0

Super!

Week in Ponza Palmarola and Ventotene COMODI – Max 4 people

Italy: Pontine Islands

6 days - 6 nights

6 departures available

July - August

Starting from

€1,028

€874

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

13 departures available

June - September

Starting from

€641

Per person

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4.8

Super!

Come and discover the Egadi Islands! Nature, relaxation and crystal clear waters

Italy: Aegadian islands

7 days - 7 nights

11 departures available

July - September

Starting from

€700

Per person

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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.

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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

13933 reviews

Squid Regatta

10/20/2026

Valentina M.

-

IT

Wonderful weekend with participation in the squid regatta that allowed us to appreciate Francesco's skills as a captain. It was fun to get involved in conducting! [hidden] is a gem of a boat: convenient spaces, clean and comfortable.
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It's time for sun and sea!

10/19/2026

Francesco G.

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IT

A special thanks goes to Carlo, exceptional owner and skipper, super welcoming, prepared and smart. He managed to make us feel immediately at ease by transmitting his passion for the sea and guaranteeing us a stay in total relaxation and safety. Very nice, comfortable and clean boat. Highly recommended experience for anyone who wants to unplug and experience the sea in an authentic way.

Magical Barcolana Weekend: the most famous regatta!

10/19/2026

LUIGI L.

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IT

Wonderful experience with a wonderful team. Strongly suggested
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Barcolana 58: a day at the most famous regatta in the world

10/18/2026

Laura P.

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IT

The Barcolana is an indescribable regatta, Antonio is an excellent captain attentive and precise, the crew a nice discovery, we can't wait to do it ❤️ again

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