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Yacht sailing holidays & skippered tours in Italy

Discover more than 426 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

426

experiences

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4.8

Super!

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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13 travellers

Starting from

€1,219

€1,875

Per person

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Maddalena and South Corsica aboard a Catamaran with Hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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2 travellers

Starting from

€1,512

€1,890

Per person

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4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

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51 travellers

€990

€1,190

Per person

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5.0

Settimana in barca a vela tra Toscana e Corsica

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€1,275

€1,500

Per person

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4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

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34 travellers

€595

€700

Per person

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4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

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28 travellers

Starting from

€667

€785

Per person

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5.0

Super!

To the Tremiti for the spring long weekends

Duration:

4 days - 3 nights

Italy:

Tremiti Islands

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4 travellers

€319

€375

Per person

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5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

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6 travellers

Starting from

€170

€200

Per person

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4.5

May Day on a Sailing Boat between Procida, Ischia and Ventotene

Duration:

4 days - 4 nights

Italy:

Pontine Islands

Give this experience a try!

€378

€420

Per person

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4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

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12 travellers

€419

€465

Per person

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4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

Give this experience a try!

Starting from

€720

€800

Per person

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4.8

Super!

Large Luxury Catamaran with Hostess - Discovering the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

Give this experience a try!

€1,251

€1,390

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

12195 reviews

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Spring in the Cinque Terre

04/15/2025

Monica L.

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Italy

E' stata un'esperienza fantastica! Chiara e Andrea ci hanno viziati e coccolati! E Silla è bellissima e superconfortevole! Consigliatissimo!
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Capri LightBlue and Positano BluSKy

04/14/2025

Stella A.

-

Argentina

Muy gentil Genaro
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Day trip with aperitif at sunset!

04/14/2025

Sandrine P.

-

Italy

Salve Sarebbe utile: - segnalare per chi si sposta con i trasporti pubblici e deve organizzare la trasferta, l'indirizzo preciso dell'ormeggio, In questo caso da Genova Prà e non Genova in modo generico, Non é stato molto carino iscriversi e scoprire DOPO che l'ormeggio non era proprio dove se lo eravamo immaginato. - aprire il gruppo WhatsApp un pò prima per magari dare l'opportunità a tutti di sentirsi ed eventualmente organizzarsi tra di noi se lo skipper non è particolarmente loquace. Barca ed equipaggio ok Per una prima esperienza con SailsSquare, ad aprile, in Liguria, meteo cosi cosi. Magari era ancora un pò prestino ma non dipende da nessuno.
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Relaxing weekend between Portovenere and the 5 Terre

04/11/2025

Fabio B.

-

Italy

molto bello! Renato disponibile a condividere la sua esperienza

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