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Sailboat yacht sailing holidays & tours in Italy

Discover more than 385 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!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

21 departures available

May - October

Starting from

€590

Per person

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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

14 departures available

June - September

Starting from

€680

Per person

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4.8

Super!

From Cagliari to Cannigione.. exploring the east coast of Sardinia

Italy: Southern Sardinia

6 days - 7 nights

One departure available

May

€550

Per person

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4.8

Super!

Sardinia and Corsica on a Classic Sailing Ship 4 cabins plus crew

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€550

€523

Per person

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4.7

Between the Pontine Islands and the Phlegraean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

7 departures available

July - September

Starting from

€795

€716

Per person

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4.7

Whale watching cruise with WWF guide for children 14-17 on an 18-meter schooner

Italy: Tuscany

6 days - 6 nights

4 departures available

June - August

Starting from

€1,052

€999

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

14 departures available

June - October

Starting from

€689

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

8 departures available

June - September

Starting from

€825

€743

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

3 departures available

July - August

Starting from

€890

Per person

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4.6

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

Italy: Northern Sardinia

6 days - 7 nights

16 departures available

May - October

Starting from

€650

€585

Per person

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4.7

In the blue of Capri and the infinity of the Amalfi Coast

Italy: Naples & Amalfi Coast

2 days - 2 nights

6 departures available

May - October

Starting from

€320

€272

Per person

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4.7

Whale watching cruise with WWF guide on an 18-meter schooner between Tuscany and Corsica

Italy: Tuscany

6 days - 6 nights

5 departures available

June - September

Starting from

€999

€949

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

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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

12700 reviews

May Day between Elba and Capraia

05/11/2026

Valeria C.

-

Italy

The weather helped us enjoy a fantastic navigation also thanks to the experience of the skipper Enrico and the comfort of the boat. Mixed crew sea... It could have gone very badly or very well and it went very well!
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Relaxing weekend in the Pontine Islands

05/11/2026

Flavia F.

-

Italy

Great experience! Stefano and Adriano welcomed us as great hosts in their beautiful "family boat". This made our holiday serene, pleasant and constructive p.s. with a group that we did not know before! All together they supported us in making the first sailing experience of our children aged 8 and 11 unforgettable... they would already like to come back! 😊 Thank you Antonietta and Remo, thank you Daniela and Paolo. Fair winds Commander!

1st May: Whale watching expedition with WWF guide on an 18-meter schooner

05/6/2026

rosanna b.

-

Italy

I am satisfied with the knowledge that Laura has transmitted to us about cetaceans, dolphins etc. the knowledge on where and how they live on what they feed and what we humans could do if we were human, to help them live better, the explanations were very simple but effective and clear Laura is very competent in the subject. Pleasant destinations for the search for cetaceans, hearing their chatter through the headphones was very pleasant. The crew helpful, the boat a little too spartan. overall it was a good experience.
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Weekend in the Pontine Islands

05/6/2026

Emanuele A.

-

Italy

Memorable experience. Fabio is an exceptional person... nice, easy-going, and expert in navigation and all the gems of the Pontine Islands. The crew, whom I did not know, was a great discovery, and a rare harmony was immediately created, thanks to the love for the sea that naturally united everyone. Definitely to be redone! Thank you Fabio, thank you sea!

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