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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.

401

experiences

401

experiences

Dream Aeolian Islands

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

Starting from

€540

€600

Per person

4.9

In the blue between Sardinia and Corsica on a sailboat

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

+111 travellers

have booked

Starting from

€650

Per person

4.0

Exclusive cruise on the new Lagoon 42 of 2024

Duration:

6 days - 7 nights

Italy:

Northern Sardinia

+7 travellers

have booked

Starting from

€533

Per person

4.5

1 Week Professional Catamaran Training - Cagliari Sardinia

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

Starting from

€1,320

Per person

Day trip to discover the Zingaro Nature Reserve

Duration:

1 day - 0 nights

Italy:

Sicily

Give this experience a try!

€100

Per person

4.8

Sorrento Coast, Capri, Positano, Amalfi. Inclusive.

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

Give this experience a try!

Starting from

€550

Per person

4.8

An unforgettable sail to discover the Egadi Islands

Duration:

3 days - 4 nights

Italy:

Aegadian islands

+17 travellers

have booked

€350

Per person

5.0

Sailing, swimming and aperitif at sunset ... What else?

Duration:

1 day - 0 nights

Italy:

Lake Garda

+4 travellers

have booked

Starting from

€69

Per person

5.0

Weekend sailing in the Pontine Islands

Duration:

2 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€250

Per person

5.0

Elba Adventure

Duration:

3 days - 2 nights

Italy:

Tuscany

+3 travellers

have booked

€335

Per person

4.5

Weekend of sea and colors between Ischia, Procida and Vivara

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

+14 travellers

have booked

Starting from

€237

€249

Per person

4.9

Weekend on the Island of Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

+13 travellers

have booked

Starting from

€228

€240

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

122 reviews

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 .

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

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

Spring long deck by catamaran in Cinque Terre

04/30/2024

Ilaria L.

Switzerland

Bellissima esperienza!

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