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Family sailing cruises yacht sailing holidays & tours in Italy

Discover more than 18 opportunities to get on board a Family sailing cruises 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

4 departures available

August

Starting from

€920

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

3 departures available

August - September

Starting from

€600

€570

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

One departure available

August - September

€1,041

Per person

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4.8

Super!

Long weekend among the wonders of Elba and Capraia

Italy: Tuscany

4 days - 3 nights

4 departures available

August - September

Starting from

€400

€360

Per person

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4.7

Long weekend of whale watching with WWF guide on an 18-meter schooner

Italy: Tuscany

3 days - 3 nights

2 departures available

September

Starting from

€452

€429

Per person

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4.7

Week between the Tuscan Islands and Northern Corsica

Italy: Tuscany

7 days - 6 nights

6 departures available

August - September

Starting from

€700

Per person

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5.0

Super!

Pure life in the Aeolian Islands: between volcanoes and crystal clear waters

Italy: Aeolian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€690

€613

Per person

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4.7

Whale watching cruise with WWF guide between Liguria and the French Riviera

Italy: Liguria

6 days - 6 nights

One departure available

July - August

€946

Per person

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4.8

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

7 departures available

August - October

Starting from

€750

€675

Per person

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4.7

Whale watching mini-cruise in the Pelagos Sanctuary with WWF guide

Italy: Liguria

4 days - 4 nights

2 departures available

September

€609

€579

Per person

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4.9

Super!

Midweek between Elba and Capraia

Italy: Tuscany

4 days - 4 nights

2 departures available

September

€400

Per person

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4.8

Super!

All in the family: 5 days between Elba and Capraia on a 17m boat - 2 boats in company

Italy: Tuscany

5 days - 4 nights

3 departures available

September

€490

€466

Per person

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Get onboard solo, with your family or your friends

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On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Family sailing cruises yacht sailing holidays & tours in Italy

418 reviews

Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

Francesca C.

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IT

It was an unforgettable experience, perfect from every point of view. The skipper is impeccable, an excellent cook and knows the sea and the Pontine islands perfectly. He is very nice and a person of heart. It is a trip that I recommend to anyone, even those who are at their first experience on a boat, like me. In addition, the places are magnificent and you will love them. Super recommended 😻
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

marco s.

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IT

If you have a city, a job and things waiting for you, don't go. Between sun, sea, food and the wonderful company of Antonio, with his kindness, generosity and stories you will never want to go home.
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Sailing cruise to the Pontine: wonders a stone's throw from Rome

07/22/2026

Luigi F.

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IT

We spent an unforgettable week with a varied but very nice crew! Antonio is a super skipper. He has passion, experience and is a great entertainer as well as an excellent chef. Always available he really made us discover the beauties of these wonderful islands. The boat is large, a bit dated but well maintained and always clean. Super recommended experience.

Cruise with WWF guide between Giglio, Giannutri and Montecristo

07/21/2026

Fabio U.

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IT

Nice experience with skipper and WWF guide above expectations. We had a very good time; We assign 5 stars to both, I speak in the plural because the members of my family have also expressed the same rating

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