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Sailboat yacht sailing holidays & tours in Italy

Discover more than 331 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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5.0

Super!

On board with the chef at the Egadi Islands

Italy: Aegadian islands

7 days - 7 nights

4 departures available

June - September

Starting from

€800

€720

Per person

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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

€759

€683

Per person

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5.0

Super!

Cruise Elba, North Corsica, Capraia PROFESSIONAL SKIPPER COOK

Italy: Tuscany

6 days - 7 nights

4 departures available

June - September

Starting from

€793

€714

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

11 departures available

June - September

Starting from

€650

Per person

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4.9

Super!

Poetic Gulf of Poets

Italy: Liguria

3 days - 2 nights

11 departures available

August - October

Starting from

€220

€187

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

5 departures available

June - September

Starting from

€935

€748

Per person

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5.0

Super!

Blu Pontino - Evasione infrasettimanale

Italy: Pontine Islands

4 days - 3 nights

2 departures available

August - October

Starting from

€180

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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4.7

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

Italy: Northern Sardinia

6 days - 7 nights

12 departures available

June - September

Starting from

€650

Per person

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5.0

Super!

North and south Sardinia of Corsica sailing

Italy: Northern Sardinia

7 days - 7 nights

9 departures available

July - September

Starting from

€750

€713

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

12 departures available

June - November

Starting from

€530

€477

Per person

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4.9

Taste of the sea between the island of Capraia and Northern Corsica

Italy: Tuscany

7 days - 7 nights

3 departures available

July - August

Starting from

€700

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

11325 reviews

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Life-changing experiences: Four days in the Pontine Islands

06/13/2025

Cristiano P.

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Italy

Fantastico. Esperienza meravigliosa. Divertente, bella, ho solo aggettivi positivi
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

armando a.

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Switzerland

È stata una bellissima esperienza con Antonio! Posti fantastici! Sarebbe stato ancora più bello navigare solo con le vele ma purtroppo le condizioni meteo e dell' equipaggio non lo permettevano. Da rifare sicuramente ;)
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Weekend at the Pontine a stone's throw from Rome

06/12/2025

Daniela B.

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Italy

Una barca d’epoca curata e amata, uno skipper di esperienza con competenze e grandi doti da intrattenitore (anche ottimo cuoco), un equipaggio piacevole e rispettoso e isole che ti rubano il cuore. Questo in sintesi il nostro we con Antonio e la sua barca, ma non possiamo ridurre a poche righe il nostro weekend. Antonio è un vero “lupo di mare” e grazie alle sue competenze ci ha raccontato storie di mare, di uomini, di isole, di uccelli migratori, di palme e di antichi romani. Le sue capacità come restauratore di barche d’epoca si apprezzano vivendo sulla sua barca che mantiene immutato il fascino di un tempo. Abbiamo visitato calette e grotte accompagnate dallo skipper che con il tender ci ha portato dove la comoda barca da 15m non poteva arrivare, dormito in rada e veleggiato quando il tempo lo consentiva. Un’esperienza da ripetere che ci ha rapito il cuore.
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Prime fughe primaverili in compagnia del mare

06/10/2025

federica c.

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Switzerland

Peccato non ci siano più di 5 stelle! Esperienza profonda con totale immersione nel mare, nel vento e nella curiosità di scoprire una passione come quella della vela. Stelia non è solo una barca stupenda ed elegante ma anche una maestra. Carlo non è solo uno skipper ma un coach calmo paziente e pieno di passioni capace di trasmettere tutta la sua esperienza ma soprattutto lasciartene sperimentare un po’. Con proposte di tante iniziative interessanti per proteggere il nostro mare a cui senza dubbio prenderò parte. Consiglio assolutamente, tornerò senza dubbio e valutazione top.

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