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Yacht sailing holidays & skippered tours in Italy

Discover more than 138 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

138

experiences

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4.9

Sailing excursion to Capri / Positano

Duration:

1 day - 0 nights

Italy:

Gulf of Naples

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+2 travellers

have booked

€160

Per person

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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

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Sea, Sail & Joy! Weekend a vela

Duration:

3 days - 2 nights

Italy:

Puglia

Give this experience a try!

€350

Per person

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4.3

Crociera 7 gg su maxi yacht vela 22 mt con skipper pontine e flegree

Duration:

6 days - 6 nights

Italy:

Pontine Islands

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+24 travellers

have booked

€1,090

Per person

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5.0

Weekend at the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+6 travellers

have booked

Starting from

€375

Per person

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5.0

Relaxing weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+45 travellers

have booked

Starting from

€325

Per person

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4.9

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+15 travellers

have booked

Starting from

€280

Per person

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4.5

Weekend in the Pontine Islands

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+10 travellers

have booked

Starting from

€280

Per person

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4.9

Life Changing Experiences - Isole Pontine

Duration:

3 days - 2 nights

Italy:

Pontine Islands

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+20 travellers

have booked

€420

Per person

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4.6

Ponza and its wonders

Duration:

3 days - 2 nights

Italy:

Pontine Islands

Give this experience a try!

€315

€350

Per person

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The hidden jewels of the Aeolian Islands

Duration:

7 days - 7 nights

Italy:

Aeolian Islands

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+27 travellers

have booked

€475

€500

Per person

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4.8

An afternoon on a boat in Alassio - ALL INCLUSIVE

Duration:

1 day - 0 nights

Italy:

Liguria

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+3 travellers

have booked

€85

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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 - Yacht sailing holidays & skippered tours in Italy

10929 reviews

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Let's discover the Aeolian Islands together by sailing

05/18/2024

Eros Giorgio M.

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Italy

Bellissime le Eolie, bella la combinazione vela ed escursioni, piacevole il gruppo e Mario un esperto ed affidabile velista.
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Weekend at the Pontine Islands: Ponza and Palmarola

05/18/2024

Giulio S.

-

Italy

Una tre giorni davvero bella. Tempo splendido, Ponza ancora con pochi turisti. Marco, oltre che uno skipper esperto, è una persona incredibile, generosa, amichevole e a Ponza conosce tanti luoghi e persone. Ci ha fatto passare momenti di relax, tra buon cibo, buona musica, belle foto scattate e tanti aneddoti. Pur essendo una persona che non fa amicizia velocemente mi sono trovato subito bene con lui e gli altri viaggiatori. Mi piacerebbe vedere le Eolie con lui. Lo consiglio!
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In the blue of Capri and the infinity of the Amalfi Coast

05/15/2024

simona b.

Esperienza stupenda! Grazie per la disponibilità e la simpatia ! A presto!
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An unforgettable sail to discover the Egadi Islands

05/14/2024

Marco B.

-

Switzerland

Bel giro, bella compagnia e ottimo equipaggio

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