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Yacht sailing holidays & skippered tours in Italy

Discover more than 228 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

228

experiences

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5.0

Weekend in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

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+13 travellers

have booked

€275

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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+5 travellers

have booked

€595

Per person

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4.8

Weekend 2 June in the colours of Elba on board a classic Ketch

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€240

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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+5 travellers

have booked

Starting from

€280

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

Give this experience a try!

Starting from

€250

Per person

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5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

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!

€250

Per person

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W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+37 travellers

have booked

€210

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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+40 travellers

have booked

Starting from

€109

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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5.0

Weekend with wine tasting between Santa Margherita Ligure and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

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+18 travellers

have booked

Starting from

€289

€340

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

10897 reviews

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Spring long deck by catamaran in Cinque Terre

04/29/2024

Marco S.

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Italy

Grande Antonio! È stato un piacere fare questa esperienza con lui. Ci ha coccolato per tutto il viaggio con la sua cucina buonissima. Persona super disponibile, divertente e piena di risorse. Barca favolosa. Ottima compagnia. Che dire… è stato tutto meraviglioso.
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Long weekend of April 25 in Elba, Corsica and Capraia

04/29/2024

Paolo G.

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Italy

Bellissima esperienza all’isola d’Elba, che non conoscevo e ho cominciato ad amare. Paolo è semplicemente fantastico! Divertente e sicuro nel condurre la barca, tutto ciò che si cerca in uno skipper. Ha saputo conciliare le esigenze di tutti, ci ha fatto andare a vela ma anche rilassare, sempre in sicurezza. Nel mangiare e fare aperitivi è un fuoriclasse! Un ponte del 25 aprile da ricordare!
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Long weekend of April 25 in Elba, Corsica and Capraia

04/29/2024

Laurent M.

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France

seul Francais a bord ne parlant pas italien avec des co-equipiers italiens, mais passionné de voile et voulant apprendre l'italien, le Capitaine Paolo a ete genialissime pour aider a m'integrer avec toutes les langues qu'il parle, supers sessions de voiles, tres belles etapes dans les marinas, et dolce vita avec tout l'équipage: j'ai adoré ces 4 jours et je repars avec toute une bande de nouveaux amis italiens !!! Paolo, je reviens des que je peux !!! Ciao a tutti amici !!!
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A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!

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