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Yacht sailing holidays & skippered tours in Italy

Discover more than 32 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

32

experiences

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4.9

Veleggiate e aperitivi all'Elba e isole vicine

Duration:

3 days - 2 nights

Italy:

Tuscany

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+6 travellers

have booked

Starting from

€333

Per person

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Sailing, swimming, snorkeling and relaxing along the coast in Castelsardo (SS)

Duration:

1 day - 0 nights

Italy:

Northern Sardinia

Give this experience a try!

€77

€85

Per person

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4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

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+19 travellers

have booked

€240

Per person

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4.9

Weekend at the Pontine Islands: Ponza and Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+3 travellers

have booked

Starting from

€260

Per person

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The hidden jewels of the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+30 travellers

have booked

€390

€410

Per person

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4.8

Seductive weekend on a sailing boat on the island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

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+36 travellers

have booked

€239

€265

Per person

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4.5

Weekend of sea and colors between Ischia, Procida and Vivara

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

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+15 travellers

have booked

€237

€249

Per person

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4.9

Basic sailing course on cabin cruisers

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€225

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!

€225

Per person

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5.0

Week-end de navigation entre Golfo Dei Poeti, Portovenere, Rosse et Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+49 travellers

have booked

€190

Per person

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Magical weekend on Giglio Island

Duration:

2 days - 2 nights

Italy:

Tuscany

Give this experience a try!

€252

€280

Per person

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5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

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+19 travellers

have booked

€180

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

10937 reviews

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Aeolian Islands - Sea, Sun and Relax - big and new Catamaran Lagoon 42

05/26/2024

Hervé L.

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France

Super accueil de Maurizio, qui nous a fait découvrir, dans une ambiance "entre amis" le cadre magique des iles éoliennes, de la dolce Vita sur Lipari au spectacle grandiose du Stromboli qui nous a gratifié de belles éruptions en directe live. Bateau nickel et programme riche d'activités.
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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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