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Yacht sailing holidays & skippered tours in Italy

Discover more than 29 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

29

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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4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

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+4 travellers

have booked

€240

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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+20 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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+8 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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+14 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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W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+37 travellers

have booked

€190

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

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

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+14 travellers

have booked

€180

Per person

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4.8

Let's discover the Aeolian Islands together by sailing

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+23 travellers

have booked

€730

Per person

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4.9

A week in the Aeolian Islands - 6 islands in 7 days

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

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+8 travellers

have booked

€450

€500

Per person

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4.0

All-inclusive Sardinia & Corsica Cruise (per cabin)

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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+108 travellers

have booked

Starting from

€1,701

€1,790

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

10905 reviews

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May 1st on Elba - Stewardess on board -3 Cab./ 3 Bathrooms

05/2/2024

susanna s.

-

Italy

una splendida vacanza . Fabio e Angela gentilissimi mi hanno offerto ogni confort a bordo e insegnato i primi rudimenti della vela .
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25 April - Whale watching expedition with WWF researcher in Liguria

05/2/2024

Rossella D.

-

Italy

Esperienza complessivamente decisamente positiva, nonostante le importanti difficoltà causate dalle pessime condizioni meteorologiche. L'estrema professionalità dello skipper e delle guide di whale watching, insieme al grande affiatamento e collaborazione che si è creato con tutto l'equipaggio, hanno fatto in modo che l'intera esperienza si vivesse nel migliore dei modi, in totale armonia, portando a casa anche grandi soddisfazioni di avvistamento di delfini, balenottere e tartarughe! Un'esperienza davvero indimenticabile, grazie di cuore!
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LONG WEEKEND 25 April barefoot: 4 days between Capraia and the island of Elba

05/1/2024

Simone D.

-

Switzerland

Prima esperienza in barca a vela , Matteo oltre che essere una bellissima persona è veramente un capitano navigato che sa metterti subito a tuo agio ! Consigliato sia a giovani che famiglie ! Tutto veramente top
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Long weekend in Capraia and North Corsica

04/30/2024

Licio M.

-

Italy

Marco è uno skipper super professionale e accogliente.con l equipaggio. Barca pulita e in ordine. Grazie a Marco e a tutto l equipaggio, super simpatici

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