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Private yacht sailing holidays with skipper in Italy

Chartering a sailing boat in Italy will let you discover a new way of travelling new way of travelling in complete freedom. Choose between a catamaran or a sailing boat and embark with an experienced skipper to discover Tuscany, Sicily, Tuscany, Sicily, Sardinia and many other destinations.

339

experiences

339

experiences

4.8

Super!

Aeolian Islands New and Large 15 Meter Lagoon Catamaran with Stewardess

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

19 travellers

Starting from

€1,219

€1,875

Per person

Maddalena and South Corsica aboard a Catamaran with Hostess

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

8 travellers

€1,512

€1,890

Per person

4.8

Super!

Emerald Flotilla: La Maddalena Archipelago with Velasquez

Duration:

7 days - 7 nights

Italy:

Northern Sardinia

62 travellers

€990

€1,190

Per person

5.0

Super!

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

Escape to the Magical Blue of the Pontine Islands

Duration:

4 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

€353

€415

Per person

4.8

Super!

Lampedusa, Lampione e Linosa fra colori magici

Duration:

7 days - 7 nights

Italy:

Pantelleria and Lampedusa

34 travellers

€595

€700

Per person

4.6

Cruise to the Maddalena Archipelago and South Corsica

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

28 travellers

Starting from

€667

€785

Per person

5.0

Super!

1 May long weekend sailing with RICCARDO PROFESSIONAL SKIPPER COOK

Duration:

4 days - 4 nights

Italy:

Tuscany

5 travellers

€374

€440

Per person

5.0

Poetic Gulf of Poets

Duration:

3 days - 2 nights

Italy:

Liguria

12 travellers

Starting from

€170

€200

Per person

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

4.9

Super!

Long weekend on Elba: 4 days of sun and sailing

Duration:

3 days - 3 nights

Italy:

Tuscany

17 travellers

Starting from

€342

€380

Per person

4.3

Sailing holiday in the archipelago of La Maddalena and Costa Smeralda

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

2 travellers

Starting from

€720

€800

Per person

Why book a holiday with Sailsquare?

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

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 more about the skipper and travellers who have already booked the holiday, to find out more about the

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 - Private yacht sailing holidays with skipper in Italy

1279 reviews

Spring long weekends on a catamaran in the Cinque Terre

04/22/2025

Silvia D.

Italy

Antonio e sua moglie Nadia sono stati fantastici: simpatici, organizzati e molto accoglienti, oltre ad essere esperti naviganti. La barca è pulita e ordinata, tenuta con cura. Gli spazi interni ed esterni sono davvero confortevoli. Nonostante il tempo, siamo riusciti a sfruttare al meglio i momenti di bel tempo. È stata una vacanza meravigliosa, da rifare! Grazie Antonio e Nadia 😉 A presto. Silvia e Riccardo

First spring getaways in the company of the sea

04/22/2025

Francesca S.

Italy

Carlo è più che uno skipper, è un vero capitano! La barca è molto comoda, confortevole pulita e spaziosa, il nostro we nonostante il tempo un po’ impervio, è stato veramente piacevole e avventuroso! Ci siamo trovati benissimo

First spring getaways in the company of the sea

04/21/2025

Michele I.

Italy

Barca nuova bellissima. Skipper preparato e affidabile. Ha saputo creare l'ambiente giusto. Consigliato a tutti

Spring in the Cinque Terre

04/15/2025

Monica L.

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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