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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.

405

experiences

405

experiences

4.8

Capri LightBlue e Positano BluSKy

Duration:

2 days - 2 nights

Italy:

Amalfi Coast

Give this experience a try!

€298

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

4.8

Sailing on Elba

Duration:

3 days - 3 nights

Italy:

Tuscany

+2 travellers

have booked

Starting from

€324

€360

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

4.9

Capraia under full sail / trekking on the island

Duration:

3 days - 2 nights

Italy:

Tuscany

+4 travellers

have booked

Starting from

€240

Per person

4.9

Between sunsets and aperitifs on a sailing boat

Duration:

7 days - 6 nights

Italy:

Tuscany

Give this experience a try!

Starting from

€400

Per person

4.5

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+5 travellers

have booked

Starting from

€269

Per person

4.9

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+15 travellers

have booked

Starting from

€269

Per person

5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+37 travellers

have booked

Starting from

€230

Per person

4.8

Weekend between Amalfi, Positano and Capri

Duration:

3 days - 2 nights

Italy:

Amalfi Coast

+18 travellers

have booked

€450

Per person

Mini-cruise to the Aeolian Islands

Duration:

3 days - 2 nights

Italy:

Aeolian Islands

Give this experience a try!

Starting from

€219

€230

Per person

4.9

Sailing weekend in Ponza and Palmarola!

Duration:

3 days - 2 nights

Italy:

Pontine Islands

+30 travellers

have booked

Starting from

€248

€275

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

124 reviews

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!

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

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