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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.

406

experiences

406

experiences

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

+48 travellers

have booked

Starting from

€99

Per person

4.6

Meditation & Sailing

Duration:

5 days - 5 nights

Italy:

Tuscany

+3 travellers

have booked

€480

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 in Capraia, the island with timeless sunsets

Duration:

2 days - 2 nights

Italy:

Tuscany

+17 travellers

have booked

Starting from

€225

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

4.3

Elba a sea of emotions - Stewardess on board - 3Cab/3Bagni

Duration:

3 days - 3 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€329

Per person

4.9

Vela Trekking e Mountain Bike

Duration:

3 days - 3 nights

Italy:

Aeolian Islands

Give this experience a try!

€265

Per person

4.5

Weekend di vela e Trekking all'Isola d'Elba

Duration:

2 days - 2 nights

Italy:

Tuscany

+2 travellers

have booked

€280

Per person

4.8

Sailing on Elba

Duration:

3 days - 3 nights

Italy:

Tuscany

+2 travellers

have booked

Starting from

€324

€360

Per person

4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

+4 travellers

have booked

Starting from

€240

Per person

Sailing in Ponza and Palmarola

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€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

126 reviews

Catamaran weekend: La Spezia, Portovevere, Lerici and Cinque Terre

05/6/2024

Paola d.

Italy

Esperienza superpositiva. Catamarano comodissimo e nuovissimo.. Molto gradita la prenotazione delle cene a terra da parte dello skipper Maurizio sempre disponibile e discreto. Grazie 😀

April 25th long weekend in Bastia

05/6/2024

Lisa V.

Italy

Bellissima esperienza. Lo Skipper Enrico oltre ad essere un ottimo uomo di mare ci ha deliziati di ottimi pranzetti e cene in barca.

25 April - 4 days sailing between La Maddalena and Bonifacio

05/3/2024

Bart S.

Spain

Excellent sailing trip in a comfortable boat with a great captain!! Grazie per tutto Leo & Crew!!!

Sailing, early sun and aperitif at sunset ... What else?

05/3/2024

Cristiana L.

Italy

Giornata stupenda! lo skipper Emanuele molto simpatico, alla mano e soprattutto molto preparato e affidabile. Abbiamo veleggiato con un bel vento, io sono interessata alla vela ed Emanuele mi ha spiegato tante cose, fatto fare delle manovre e riposto pazientemente a tutte le mie tante domande. Abbiamo anche fatto un bellissimo aperitivo all'ancora. Non posso che consigliare vivamente questa esperienza!

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