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Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

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4.9

The magic of the Egadi Islands aboard a brand new catamaran

Italy: Aegadian islands

7 days - 7 nights

3 departures available

August - October

Starting from

€950

Per person

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4.7

Maddalena Archipelago, southern Corsica: wonderful Sardinia

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

September - October

Starting from

€700

Per person

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4.8

Super!

Barefoot holiday: 2 boats between Tuscany and Corsica with professional skipper

Italy: Tuscany

6 days - 7 nights

One departure available

August

€1,100

Per person

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4.7

Feast of Santa Candida in Ventotene

Italy: Pontine Islands

3 days - 3 nights

One departure available

September

€420

€378

Per person

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5.0

Super!

Learn to sail in Liguria: First level sailing course

Italy: Liguria

2 days - 1 night

One departure available

October

€220

Per person

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4.8

Super!

Week end in Costa Azzurra

Italy: Liguria

2 days - 2 nights

One departure available

August - September

€360

€324

Per person

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5.0

Super!

Sailing week North Sardinia and South Corsica

Italy: Northern Sardinia

6 days - 6 nights

One departure available

August - September

€950

Per person

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4.8

Super!

Aeolian Islands: between sea and authentic flavours

Italy: Aeolian Islands

7 days - 7 nights

5 departures available

September - October

Starting from

€750

€675

Per person

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4.9

Super!

Gulf of Poets

Italy: Liguria

3 days - 2 nights

One departure available

September

€280

Per person

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5.0

Super!

Long Weekend Santa Candida - Ventotene

Italy: Pontine Islands

5 days - 4 nights

One departure available

September

€550

Per person

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5.0

Tuscany and Corsica: sailing sun adventure good food energy and well-being

Italy: Tuscany

3 days - 3 nights

3 departures available

August - September

Starting from

€350

Per person

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4.8

Super!

Fabulous Egadi Islands by catamaran - Stewardess on board

Italy: Aegadian islands

6 days - 7 nights

One departure available

September

€1,100

Per person

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

Reviews - Private yacht sailing holidays with skipper in Italy

3271 reviews

Gargano National Park and Marine Protected Area of the Tremiti Islands

08/22/2026

Antonella B.

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IT

This 5-day sailing experience with Marco was a pleasant discovery and I would recommend it to anyone. Not only do you visit beautiful places in themselves, the Tremiti islands and the Gargano, but they are experienced in an authentic way: full but relaxed, far from the usual experiences. Spending a night in the roadstead, observing the starry sky together, surrounded by a splendid white cove dominated by the forest of the Gargano park, where the wind and the sea determined the destination: this is for me the essence of this trip. Marco is a multifaceted person, who has filled our hearts and heads with experiences, knowledge and emotions, making us feel at ease and always safe; It was a pleasure to share this holiday with him and the rest of the crew! ☺️
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Island of Elba and South Corsica fantastic week

08/22/2026

Myriam C.

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IT

I would have liked to go a little sailing instead of always motoring! For the rest wonderful places, fun and nice people, captain a little too rigid with the crew!
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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms

08/22/2026

Emanuele P.

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IT

Beautiful experience, supercompetent skipper (Luca and Tommaso) who ensured most of the sailing even when many boats remained in port or roadstead. Program respected greatly. Beautiful crew and level kitchen and assistance. Absolutely to recommend

Flotilla Smeralda: La Maddalena Archipelago with Velasquez - MEN'S SEATS ONLY

08/22/2026

Luca A.

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IT

Hello, Congratulations for the organization and management of the entire week. The destinations were very beautiful, the company on my boat Virgo and also on all the others that made up the flotilla was very pleasant. The management of the initial expense on the first day (for galley) needs to be deepened and reviewed. Anyway, congratulations. Greetings Luca .

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