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Sailboat yacht sailing holidays & tours in Italy

Discover more than 293 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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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Italy: Pontine Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€719

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

5 departures available

July - September

Starting from

€650

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Italy: Northern Sardinia

7 days - 7 nights

2 departures available

August

€1,190

Per person

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5.0

Super!

North and south Sardinia of Corsica sailing

Italy: Northern Sardinia

7 days - 7 nights

3 departures available

July - August

Starting from

€900

€810

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

2 departures available

August - October

Starting from

€200

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

2 departures available

August - September

Starting from

€793

€714

Per person

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4.7

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

Italy: Northern Sardinia

6 days - 7 nights

9 departures available

July - September

Starting from

€650

Per person

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4.9

Super!

Week of sea, nature and fun in the Egadi Islands!

Italy: Aegadian islands

7 days - 7 nights

7 departures available

July - September

Starting from

€690

€621

Per person

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4.8

Super!

Sardinia and Strait of Bonifacio on a 50-foot sailboat

Italy: Northern Sardinia

6 days - 7 nights

3 departures available

July - August

Starting from

€780

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in seven days

Italy: Aeolian Islands

7 days - 7 nights

9 departures available

August - November

Starting from

€530

€477

Per person

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5.0

Super!

Aeolian Islands - A week on a sailing boat with skipper and assistant

Italy: Aeolian Islands

7 days - 7 nights

3 departures available

July - August

Starting from

€935

€748

Per person

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5.0

Super!

Weekend Elba o Capraia

Italy: Tuscany

2 days - 2 nights

6 departures available

July - September

Starting from

€293

€264

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 - Sailboat yacht sailing holidays & tours in Italy

11464 reviews

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Weekend a Capraia, trekking e natura

07/5/2025

Sonia G.

-

Italy

Non ero mai salita su una barca... e stata la mia prima volta... devi dure che è stata un esperienza bellissima... un weekend indimenticabile.. che porterò sempre nel mio cuore.... lo skipper Francesco una persona formidabile....simpatico...gentile.... ..disponibile... e soprattutto molto bravo anche in cucina... ci ha sorpreso con i suoi primi veramente molto buoni... Sicuramente un esperienza da ripetere...
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On board with the chef at the Egadi Islands

07/5/2025

Francesca S.

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Italy

Bellissima esperienza, al solito! Ottimo capitano - chef bella barca con la prua coperta con cuscini per il sole. Tempo bello anche se a volte molto caldo. Belle le isole con sempre qualcosa da scoprire.
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Daily sailing in the Tavolara Marine Park

07/5/2025

Chiara C.

-

Italy

È stata una giornata bellissima! Ada e Valerio sono due persone superaccoglienti e molto molto interessanti, oltre che due skipper coi fiocchi, con tantissimi anni e tantissime miglia di esperienza. La barca è un gioiello! Grazie!
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Daily sailing in the Tavolara Marine Park

07/5/2025

Claudio C.

Ada e Valerio sono delle persone splendide. Aperte, ospitali, entusiaste della vita e del mondo che ci ospita. La giornata è stata attiva e coinvolgente (sono dei velisti esperti disponibilissimi a condividere competenze ed esperienze), interessante, piacevole. Mille grazie con un abbraccio, anche alla loro scattante e comoda [hidden].

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