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Yacht sailing holidays & skippered tours in Italy

Discover more than 43 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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4.8

Super!

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

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€660

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

5 departures available

July - September

Starting from

€990

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

One departure available

August

Starting from

€1,150

Per person

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4.9

Super!

The Aeolian Islands, the sea and the slowing down of time; a week on a catamaran

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€1,450

€1,305

Per person

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5.0

Super!

Sailing cruise between the Maddalena archipelago and Corsica

Italy: Northern Sardinia

6 days - 6 nights

5 departures available

August - September

Starting from

€800

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

4 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

5 departures available

July - 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

5 departures available

July - September

Starting from

€700

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

5 departures available

July - September

Starting from

€850

€765

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

5 departures available

July - September

Starting from

€778

€700

Per person

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4.4

Premium

SARDINIA Paradise - Catamaran cruise with hostess FULL BOARD

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

July - September

Starting from

€1,525

€1,373

Per person - min 2 pax

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4.9

Day in the Gulf of Tigullio on a Sailing Boat

Italy: Liguria

1 day - 0 nights

5 departures available

July - August

€130

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.

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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 - Yacht sailing holidays & skippered tours in Italy

15149 reviews

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Feast of Santa Candida in Ventotene

11/9/2026

Gennaro A.

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IT

Pleasant holiday in an always suggestive setting. The feast of Santa Candida in Ventotene is a pleasant discovery and every year I gladly go back ...

It's time for sun and sea!

11/5/2026

francesca t.

-

IT

All very nice !! and Carlo... A very good sailor and a very kind and hospitable person !! Francesca
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Everyone in Totani towards Capraia: let's experience the Festival on a sailing boat!

11/3/2026

Paolo P.

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IT

Excellent experience, boat up to expectations, skipper attentive to the safety of the crew and always available to evaluate every request of the people on board. To repeat the adventure for other destinations.
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Squid Festival 2026! - Capraia Isola

11/3/2026

Andrea C.

-

IT

Good experience, too bad for the weather conditions not ideal.

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