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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.

523

experiences

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Weekend Sailing in Capraia

Duration:

3 days - 3 nights

Italy:

Tuscany

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+3 travellers

have booked

Starting from

€400

Per person

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5.0

The boat all to yourself!

Duration:

3 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€425

Per person

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4.5

Weekend YOGA in barca a vela

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€370

Per person

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4.6

Spinnaker and Gennaker course: hoisting/lowering manoeuvres and adjustments

Duration:

2 days - 2 nights

Italy:

Liguria

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+3 travellers

have booked

€280

Per person

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5.0

Weekend getaway in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€350

Per person

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4.8

Week 2 June at the Egadi Islands between Nature, Relaxation & Fun

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+6 travellers

have booked

€495

Per person

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4.2

Relaxing weekend between Portovenere and the 5 Terre

Duration:

2 days - 2 nights

Italy:

Liguria

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+11 travellers

have booked

Starting from

€280

Per person

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4.9

A day of sailing in the Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€99

Per person

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4.8

Weekend cruise from Trieste in Slovenia

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

Starting from

€250

Per person

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4.7

Two hearts and a sailboat: discovering the Phlegrean Islands

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

Starting from

€225

Per person

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5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+84 travellers

have booked

Starting from

€109

Per person

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4.8

Capri LightBlue e Positano BluSKy

Duration:

2 days - 2 nights

Italy:

Amalfi Coast

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+2 travellers

have booked

€249

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

10936 reviews

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Weekend catamaran in Portovenere and Cinque Terre

05/21/2024

Ursula H.

-

Germany

Es waren zwei sehr schöne Tage, leider ohne Wind. Wunderschöne Städtchen und Strände, lecker essen. Sehr netter Skipper.
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Weekend of sea and colors between Ischia, Procida and Vivara

05/21/2024

Juri R.

-

Germany

Se sei ancora indeciso…PRENOTA! Visitare Procida e Ischia con Emiliano e Ida é molto di più di un semplice tour in barca a vela. Emiliano é un velista esperto che conosce bene le coste di Napoli e dintorni, con lui ti potrai sentire al sicuro sulla barca. Potrai decidere dove fermarti, se attraccare al porto per la notte o semplicemente visitare qualche isola e godere del buon cibo. Ad ogni modo non dovrai fare altro che rilassarti e goderti la magica atmosfera che si crea con i tuoi compagni di viaggio perché tanti aperitivi e risate al tramonto sono assicurati. E`stata davvero una bella esperienza, Emiliano e Ida sono fantastici e ci hanno fatti sentire come a casa. Grazie ragazzi per questo indimenticabile Weekend! Agnese e Juri.
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Weekend of sea and colors between Ischia, Procida and Vivara

05/21/2024

Annalisa S.

-

Italy

Disponibilità flessibilità amicizia. Emiliano uno skipper perfetto e Ida super. La barca è davvero grande comoda e pulita. Forniti di tutto lenzuola asciugamani e coperta ben lavati. Siamo stati benissimo a loro tutta la mia riconoscenza per un weekend rilassante e piacevole Raccomandatissimi!
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Weekend catamaran in Portovenere and Cinque Terre

05/21/2024

LAURA F.

-

Italy

Antonio è un ottimo skipper e un ottimo cuoco!

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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

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