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Yacht sailing holidays & skippered tours in Italy

Discover more than 106 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

106

experiences

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4.5

North Sardinia and South Corsica by catamaran with flybridge

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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87 travellers

Starting from

€799

€940

Per person

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4.2

Easter in Portofino - sailing between the Gulf of Poets and the Tiguillio

Duration:

3 days - 3 nights

Italy:

Liguria

Give this experience a try!

€332

€390

Per person

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4.5

Isole Egadi, Riserva dello Zingaro, San Vito Lo Capo - Hostess a bordo

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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5.0

Easter Sailing: Explore the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€495

€550

Per person

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5.0

April 25th and May 1st: sailing to the Egadi Islands from Palermo!

Duration:

5 days - 4 nights

Italy:

Aegadian islands

Give this experience a try!

€504

€560

Per person

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5.0

Route to the Egadi Islands: Wind, Flavors and Sea

Duration:

7 days - 7 nights

Italy:

Aegadian islands

Give this experience a try!

Starting from

€585

€650

Per person

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5.0

Aeolian Islands: between sea and authentic flavours

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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44 travellers

Starting from

€765

€850

Per person

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5.0

Super!

On board with the chef at the Egadi Islands

Duration:

7 days - 7 nights

Italy:

Aegadian islands

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56 travellers

Starting from

€675

€750

Per person

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4.9

Super!

Sunny weekend on Elba from Friday to Sunday

Duration:

3 days - 2 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€261

€290

Per person

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4.9

Super!

Easter sailing between the islands: Elba and Capraia

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€356

€395

Per person

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4.9

Super!

1st May of Gran Vela: Elba, Corsica and Capraia

Duration:

5 days - 4 nights

Italy:

Tuscany

Give this experience a try!

€428

€475

Per person

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4.9

Super!

2 June Sailing between the island of Giglio and Elba

Duration:

4 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€356

€395

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

12187 reviews

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Weekend of theoretical and practical course

12/8/2024

Fabio M.

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Italy

Gianpaolo è un bravissimo skipper, ha saputo coinvolgere tutto l'equipaggio. Utilissimi i suoi consigli
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Weekend of theoretical and practical course

11/27/2024

Matteo S.

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Italy

Gianpaolo è stato straordinario. Pozzo di conoscenza e di voglia (e pazienza) di condividerla in maniera efficace e pratica. Accogliente sia lui che la barca. Comodo anche arrivare al molo e parcheggiare eventuale mezzo di trasporto. La barca (per quella che è la mia poca esperienza in merito ancora) si è dimostrata molto adeguata alle applicazioni sia teoriche che pratiche e per imparare. Da rifare sicuramente, consiglio decisamente !!!
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Capraia and Totani, let's go!

11/10/2024

Pablo C.

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Italy

Ci siamo trovati molto bene con Ivo: skipper professionale, cuoco provetto e persona gioviale con tanto da raccontare! La sua barca è in ottime condizioni e ben pulita. Torneremmo volentieri in barca con lui.
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Capraia: squid, walking and sailing!

11/4/2024

camilla t.

-

Italy

Alessandro è stato molto carino, gentile e disponibile ! Consigliatissimo :)

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