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Yacht sailing holidays & skippered tours in Italy

Discover more than 251 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

251

experiences

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5.0

Weekend getaway in Capraia

Duration:

2 days - 2 nights

Italy:

Tuscany

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+2 travellers

have booked

€350

Per person

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4.8

Week 2 June at the Egadi Islands between Nature, Relaxation & Fun

Duration:

6 days - 7 nights

Italy:

Aegadian islands

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+5 travellers

have booked

€495

Per person

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4.2

Relaxing weekend between Portovenere and the 5 Terre

Duration:

2 days - 2 nights

Italy:

Liguria

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+5 travellers

have booked

Starting from

€280

Per person

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4.9

A day of sailing in the Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

Give this experience a try!

€99

Per person

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4.8

Weekend cruise from Trieste in Slovenia

Duration:

2 days - 2 nights

Italy:

Venice and the Gulf of Trieste

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+4 travellers

have booked

Starting from

€250

Per person

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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

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4.7

Two hearts and a sailboat: discovering the Phlegrean Islands

Duration:

2 days - 2 nights

Italy:

Gulf of Naples

Give this experience a try!

€250

Per person

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4.8

Capri LightBlue e Positano BluSKy

Duration:

2 days - 2 nights

Italy:

Amalfi Coast

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+2 travellers

have booked

€249

Per person

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5.0

Weekend with wine tasting between Santa Margherita Ligure and Portofino

Duration:

2 days - 2 nights

Italy:

Liguria

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+21 travellers

have booked

Starting from

€289

€340

Per person

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5.0

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

Duration:

1 day - 0 nights

Italy:

Lake Garda

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+86 travellers

have booked

Starting from

€109

Per person

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5.0

W.E Golfo Dei Poeti-Portovenere-Rosse-Ferale

Duration:

2 days - 2 nights

Italy:

Liguria

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+51 travellers

have booked

€210

Per person

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4.8

Long weekend exploring the Aeolian Islands

Duration:

4 days - 3 nights

Italy:

Aeolian Islands

Give this experience a try!

€340

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.

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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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