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Yacht sailing holidays & skippered tours in Italy

Discover the beauty of Italy and treat yourself to a sailing holiday of relaxation, fun, and unique landscapes. Sail around the beautiful islands of Sicily and Sardinia, discover the Lipari, Pontine and Aegadian Islands by boat or anchor in the romantic bays of Tuscany or Cinque Terres.

396

experiences

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4.6

Flottiglia Different: Party e nuovi amici alle isole Eolie

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+133 travellers

have booked

Starting from

€999

€1,175

Per person

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4.7

The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands

Duration:

7 days - 7 nights

Italy:

Naples & Amalfi Coast

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+45 travellers

have booked

Starting from

€1,253

Per person

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4.9

Super!

Beautiful bays between North Sardinia and South Corsica on a catamaran

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+85 travellers

have booked

€998

€1,050

Per person

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4.9

Super!

A week of sea, nature and fun in the Pontine Islands!

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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+67 travellers

have booked

Starting from

€621

€690

Per person

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4.8

Super!

Wandering on a sailboat, sailing in the Tuscan Archipelago

Duration:

7 days - 7 nights

Italy:

Tuscany

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+40 travellers

have booked

Starting from

€590

€850

Per person

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4.7

The Wild Flotilla: dive into the wilderness of Tuscany

Duration:

7 days - 7 nights

Italy:

Tuscany

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+31 travellers

have booked

€990

€1,190

Per person

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4.7

Whale watching cruise with WWF in Liguria between Portofino and Cinque Terre

Duration:

6 days - 6 nights

Italy:

Liguria

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+49 travellers

have booked

Starting from

€749

Per person

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4.9

Super!

A week in the Aeolian Islands - 6 islands in 7 days

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+53 travellers

have booked

Starting from

€450

€500

Per person

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4.6

Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

Duration:

7 days - 7 nights

Italy:

Pontine Islands

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+52 travellers

have booked

Starting from

€799

€900

Per person

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4.7

Whale watching cruise with WWF researcher between Elba, Capraia and North Corsica

Duration:

6 days - 7 nights

Italy:

Tuscany

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+31 travellers

have booked

Starting from

€940

€989

Per person

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5.0

Super!

Tuscan Archipelago and Northern Corsica

Duration:

7 days - 7 nights

Italy:

Tuscany

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+22 travellers

have booked

€800

Per person

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4.9

Super!

Velasquez Flotilla: Northern Sardinia and La Maddalena Archipelago

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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+17 travellers

have booked

Starting from

€990

€1,100

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

11240 reviews

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Sardinia and Corsica on a 17-metre sailboat with 4 cabins and 4 bathrooms plus crew

07/20/2024

edoardo m.

-

Italy

Naviga con Luca: un'avventura indimenticabile in barca a vela! 5 stelle su 5 Ho avuto la fortuna di vivere un'esperienza indimenticabile in barca a vela con Luca, un comandante esperto e appassionato che mi ha guidato alla scoperta dell'arcipelago della Maddalena e della Corsica del Sud. Cosa mi è piaciuto: L'itinerario mozzafiato: 1. abbiamo navigato tra isole paradisiache e calette incontaminate, godendo di paesaggi mozzafiato. 2. La passione e l'esperienza di Luca: un vero maestro di vela, capace di trasmettere la sua passione per il mare e di far vivere un'esperienza unica ai suoi ospiti. 3. La possibilità di imparare le tecniche di vela: ho avuto modo di imparare alcune nozioni base di navigazione e di provare a condurre la barca sotto la guida esperta di Luca. 4. I momenti di relax e convivialità: a bordo della Nayaca si è creata un'atmosfera amichevole e conviviale, perfetta per godersi appieno la vacanza. 5. L'impegno sociale di Luca: il suo progetto sostiene la cultura del mare e la vela, promuovendo valori importanti come il rispetto per l'ambiente e la valorizzazione del territorio. Cosa non mi è piaciuto: 6. Nulla, è stata un'esperienza davvero perfetta! Consiglio vivamente questa esperienza a tutti coloro che amano il mare, la vela e la natura.
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Maddalena Archipelago, southern Corsica: wonderful Sardinia

07/20/2024

maria rosaria anna C.

-

Italy

Vacanza PAZZESCA !! Luoghi meravigliosi , compagnia meravigliosa , simpatica e molto stimolante. Massimo è un vero skipper oltre ad essere super simpatico e gioviale e la cucina ed il sarcasmo di halby sono eccezionali. La traversata in barca vela è stata un’esperienza unica!! Una vera figata
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Holiday and sailing school between the Tuscan archipelago and Corsica

07/20/2024

roberto c.

-

Italy

Consiglio Diego a tutti, sia agli appassionati di vela che ai vacanzieri.
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Between the Pontine Islands and the Phlegrean Islands by Sailing Boat

07/20/2024

Maria Elena P.

-

Italy

Non posso che lasciare 5 stelle. Gruppo simpatico e skipper eccezionale, il migliore delle mie precedenti 8 esperienze in barca a vela. Super disponibile, affabile simpatico. La società inoltre il primo giorno ci ha omaggiato di una simpatica maglietta . Che dire? Arrivederci al prossimo anno

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Guides & tips


Italy

Tuscany, Sardinia, the Aeolian Islands and Liguria are just some of the most beautiful destinations for a sailing or catamaran holiday, let's discover them all!
Guide to Italy on a sailing boat

Tuscany

The island of Elba, Capraia, Il Giglio and Giannutri are just some of the best destinations for a sailing or catamaran vacation in Tuscany.
Guide to the Tuscany on a sailing boat

Aeolian Islands

Stromboli, Vulcano and Lipari are just some of the best destinations for a sailing or catamaran vacation in Sardinia.
Guide to the Aeolian Islands on a sailing boat

Sardinia

Costa Smeralda, Maddalena Archipelago and San Pietro Island are just some of the best destinations for a sailing or catamaran holiday in Sardinia.
Guide to the Sardinia on a sailing boat

Capri, Ischia and Procida

Enchanted landscapes and elegant haunts, thermal springs and seabeds full of surprises, simplicity and glamour: there is more than one reason to choose these timeless islands as a destination for a yachting holiday in stages.
Guide to Capri, Ischia and Procida on a sailing boat

Amalfi Coast

Positano, Amalfi and Cetara are just some of the best destinations for a sailing or catamaran holiday in the Gulf of Naples.
Guide to the Amalfi Coast on a sailing boat

WWF Whale watching cruises

A close-to-nature sailing cruise that integrates unrepeatable emotions and new scientific knowledge, perfect for true lovers of the sea, ready to have fun, wonder and delve into the magical world of cetaceans.
Guide to the WWF Cruises

Catamaran vacations

An alternative to the sailboat, the catamaran is an ideal choice for those who do not want to give up comfort and convenience and for a first vacation at sea.
Guide to the catamaran vacations

Flotilla holiday

A perfect vacation for singles (and others) to experience sailing, meet new friends and multiply the fun.
Guide to the flotilla holidays

Singles and solo travellers

Set out alone and return enriched by an unparalleled baggage of freedom, new friendships and lasting bonds. It is on a sailboat that an adventure as a solo traveler turns into a unique sharing experience.
Guide to solo travellers sailing holidays

Sailing vacations for families

To leave with one's family and return home enriched by an unparalleled baggage of adventure, bonds and indelible memories.
What to know before you go sailing with your family?

Sailing with children

Have you ever wondered if there is a vacation that is both the best for children and parents? The answer is yes, and it is indeed on a sailboat!
Guide to sailing vacations with children

Italy: the most beautiful places to sail

Italy: departures by month

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