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Yacht sailing holidays & skippered tours in Italy

Discover more than 18 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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5.0

Super!

The Squid Festival in Capraia

Italy: Tuscany

2 days - 2 nights

One departure available

October - November

€350

Per person

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4.8

Super!

The sea and sailing in autumn: two days on Elba

Italy: Tuscany

2 days - 2 nights

2 departures available

November

€190

Per person

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4.9

Super!

Long weekend at the Capraia Squid Festival

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€350

Per person

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4.8

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

One departure available

November

€299

Per person

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5.0

Squid Festival 2025 on a sailing boat

Italy: Tuscany

3 days - 2 nights

One departure available

October - November

€390

€350

Per person

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5.0

A day sailing in the fantastic Gulf of Trieste

Italy: Venice and the Gulf of Trieste

1 day - 0 nights

One departure available

November

€99

Per person

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3.0

7 islands in comfort and convenience

Italy: Aeolian Islands

6 days - 6 nights

One departure available

November

€600

Per person

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Day Cruise- Tour Golfo Dei Poeti

Italy: Liguria

1 day - 0 nights

16 departures available

November

€86

Per person

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4.0

Sagra del totano a Capraia 2025

Italy: Tuscany

3 days - 3 nights

One departure available

October - November

€390

Per person

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A terrace overlooking the sea: a day to discover the Gulf of Naples

Italy: Naples & Amalfi Coast

1 day - 0 nights

One departure available

October

€110

Per person

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Daily sailing trip off the coast of beautiful Pisa

Italy: Tuscany

1 day - 0 nights

5 departures available

November

Starting from

€115

Per person

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5.0

Magical weekend on Giglio Island

Italy: Tuscany

2 days - 2 nights

5 departures available

October - November

Starting from

€220

€198

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

13747 reviews

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North-East Sardinia and South Corsica on a sailing boat with gourmet cuisine

10/25/2025

Teresa B.

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Germany

We were very lucky to spend 7 days with Bledar on his sailboat around Sardinia and Corsica and it was unforgettable! Every day, Bledar surprised us with new, freshly prepared culinary highlights - fresh, creative and prepared with a lot of love. He took care of us touchingly, left nothing to be desired and led us to the most beautiful bays, islands and snorkeling spots. We got to know wonderful people and thanks to his warm nature, everything felt like a vacation with friends. This week was the perfect mix of relaxation, adventure and enjoyment. It was the best holiday we have ever had. Thank you, dear Bledar, for this magical time! ❤️⛵️ Tuttepossible!
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Barcolana weekend in Trieste and surroundings.

10/24/2025

Marilisa V.

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Italy

Marino skipper of great experience and sympathy; Super event and experience just as much!
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Weekend in Capraia, the island with timeless sunsets

10/22/2025

D. D.

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Italy

Great weekend !! Sailing until the last breath, all with a good skipper and also crew
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Relaxing weekend between Portovenere and the 5 Terre

10/21/2025

Manuela S.

-

Italy

Fully satisfied Advice to live a unique experience.

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