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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.

392

experiences

392

experiences

4.6

Sicily on a Sailing Boat in the Egadi Islands

Duration:

6 days - 7 nights

Italy:

Aegadian islands

+4 travellers

have booked

Starting from

€499

Per person

5.0

All inclusive day trip sailing around the Golfo Paradiso - flex dates

Duration:

1 day - 0 nights

Italy:

Liguria

+20 travellers

have booked

Starting from

€126

€140

Per person

5.0

Aeolian Islands - Volcanoes, Sail & Trekking

Duration:

6 days - 7 nights

Italy:

Aeolian Islands

+4 travellers

have booked

€1,100

Per person

4.8

Little sailors grow up: 5 days sailing on the island of Elba

Duration:

4 days - 4 nights

Italy:

Tuscany

+3 travellers

have booked

€490

Per person

4.8

All in the Family: 5 days sailing on Elba on a comfortable 17m boat

Duration:

4 days - 4 nights

Italy:

Tuscany

+7 travellers

have booked

€490

Per person

The Aeolian Islands in an exclusive boat

Duration:

6 days - 6 nights

Italy:

Aeolian Islands

+4 travellers

have booked

Starting from

€650

Per person

4.5

Sailing on the Island of Elba

Duration:

3 days - 4 nights

Italy:

Tuscany

+2 travellers

have booked

€350

Per person

5.0

A fantastic day on a boat in the blue sea of Tuscany

Duration:

1 day - 0 nights

Italy:

Tuscany

Give this experience a try!

€130

Per person

5.0

A wonderful day.... on Lake Garda - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Lake Garda

+40 travellers

have booked

Starting from

€99

Per person

4.6

Meditation & Sailing

Duration:

5 days - 5 nights

Italy:

Tuscany

Give this experience a try!

€490

Per person

5.0

Trekking & Sailing Experience-Weekend lungo a Capraia in compagnia

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

€361

€380

Per person

5.0

Weekend sailing among the Pontine Islands

Duration:

3 days - 3 nights

Italy:

Pontine Islands

Give this experience a try!

Starting from

€360

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

120 reviews

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!

Spring long deck by catamaran in Cinque Terre

04/30/2024

Imma i.

Italy

Antonio, oltre ad essere uno skipper eccezionale, è anche una gran brava persona! Consiglio vivamente un viaggio con lui e la sua Cassiopea. Buon vento, Antonio!

Long weekend in Capraia and North Corsica

04/30/2024

Marcello O.

Italy

Bel giro tra Capraia e Corsica... e poi abbiamo visto anche le balene al largo della Corsica!!! Marco, lo skipper, dovrebbe scrivere un libro su tutte le sue esperienze vissute che ti racconta tra una bolina e un'altra... Alla prossima!

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