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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.

391

experiences

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4.8

Super!

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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19 travellers

Starting from

€1,219

€1,875

Per person

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Maddalena and South Corsica aboard a Catamaran with Hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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7 travellers

Starting from

€1,512

€1,890

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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62 travellers

€990

€1,190

Per person

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5.0

Super!

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,275

€1,500

Per person

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Escape to the Magical Blue of the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€353

€415

Per person

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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28 travellers

Starting from

€667

€785

Per person

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5.0

Super!

1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

Duration:

4 days - 4 nights

Italy:

Tuscany

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5 travellers

€374

€440

Per person

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5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

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12 travellers

Starting from

€170

€200

Per person

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4.5

May Day on a Sailing Boat between Procida, Ischia and Ventotene

Duration:

4 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€378

€420

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

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17 travellers

Starting from

€342

€380

Per person

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4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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2 travellers

Starting from

€720

€800

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

12198 reviews

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Spring long weekends on a catamaran in the Cinque Terre

04/22/2025

Silvia D.

-

Italy

Antonio e sua moglie Nadia sono stati fantastici: simpatici, organizzati e molto accoglienti, oltre ad essere esperti naviganti. La barca è pulita e ordinata, tenuta con cura. Gli spazi interni ed esterni sono davvero confortevoli. Nonostante il tempo, siamo riusciti a sfruttare al meglio i momenti di bel tempo. È stata una vacanza meravigliosa, da rifare! Grazie Antonio e Nadia 😉 A presto. Silvia e Riccardo
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First spring getaways in the company of the sea

04/22/2025

Francesca S.

-

Italy

Carlo è più che uno skipper, è un vero capitano! La barca è molto comoda, confortevole pulita e spaziosa, il nostro we nonostante il tempo un po’ impervio, è stato veramente piacevole e avventuroso! Ci siamo trovati benissimo
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First spring getaways in the company of the sea

04/21/2025

Michele I.

-

Italy

Barca nuova bellissima. Skipper preparato e affidabile. Ha saputo creare l'ambiente giusto. Consigliato a tutti
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Spring in the Cinque Terre

04/15/2025

Monica L.

-

Italy

E' stata un'esperienza fantastica! Chiara e Andrea ci hanno viziati e coccolati! E Silla è bellissima e superconfortevole! Consigliatissimo!

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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

Other travel ideas

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