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Yacht sailing holidays & skippered tours in Italy

Discover more than 193 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

4 departures available

August - September

Starting from

€680

€590

Per person

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4.8

Super!

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

5 departures available

August - September

Starting from

€590

Per person

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4.6

Premium

Catamaran cruise in Sardinia & Corsica with chef - full board (per cabin)

Italy: Northern Sardinia

7 days - 7 nights

5 departures available

August - September

Starting from

€1,640

€1,558

Per person - min 2 pax

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

2 departures available

August - September

Starting from

€950

Per person

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4.6

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

Starting from

€1,260

€1,134

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

4 departures available

August - September

Starting from

€795

€716

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

5 departures available

August - September

Starting from

€600

€570

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

3 departures available

August - September

Starting from

€950

€855

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

3 departures available

August - September

Starting from

€689

Per person

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4.9

Super!

Sailing holiday in the turquoise blue waters of Corsica

Italy: Tuscany

7 days - 7 nights

One departure available

August

€890

Per person

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4.7

Weekend Elba or Capraia

Italy: Tuscany

2 days - 2 nights

3 departures available

August

Starting from

€300

€270

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

3 departures available

August - September

Starting from

€999

€949

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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 - Yacht sailing holidays & skippered tours in Italy

13839 reviews

June 2 long weekend between Capraia and Corsica - 2 boats

06/4/2026

Rebecca C.

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IT

It was a beautiful holiday, we sailed between Elba and Capraia and both Matteo and Alessio (the skippers of the two boats) were impeccable, really good and professional. On board I found a wonderful company that made these 4 days truly unforgettable! Super recommended experience
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Four days in the Pontine Islands

06/4/2026

Guido V.

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IT

Super experience with Dario!! I highly recommend it. Thank you Dario and see you next time
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Four days in the Pontine Islands

06/4/2026

miriam p.

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IT

Really nice experience. Dario is a helpful and kind person. We felt at ease on the boat right away. Will definitely recommend to other friends
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Capri Light Blue - Two boats in company!

06/4/2026

Christian C.

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IT

It's not the first trip I've made with SailSquare, but I can say without hesitation that this was one of the most beautiful experiences I've had so far. Gennaro is an extraordinary skipper and owner: he combines great technical expertise and deep sea experience with a rare ability to put everyone at ease. Always serene, helpful, never tense, always attentive to the safety and harmony of the group. He is one of those people who convey trust from the first moment and with whom it is pleasant to share time, conversations and emotions. Thanks to him we spent unforgettable days, sailing in total safety but above all in an atmosphere of authentic conviviality. On her boat you feel like guests, not customers: it is cared for in every detail, welcoming, full of comfort and attention that make you feel how much it is loved and lived by those who drive it. I take home wonderful views, new friendships and memories that will last a long time. A heartfelt thank you to Gennaro for the passion, culture, humanity and elegance with which he accompanied us in this experience. I really hope to be back on board his boat soon.

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