header cover

Yacht sailing holidays & skippered tours in Italy

Discover more than 99 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

99

experiences

cover image
avatar image

4.8

Vang Sheeting and TRIM on a state-of-the-art sailboat

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

Starting from

€140

Per person

cover image
avatar image

5.0

Sailing to the 5 Terre and Portovenere - Pearls of Liguria

Duration:

2 days - 2 nights

Italy:

Liguria

Give this experience a try!

€250

Per person

cover image
avatar image

5.0

Sailing day in the Ligurian nature, boarding from Varazze

Duration:

1 day - 0 nights

Italy:

Liguria

avatar image

chiara c.

has booked

€95

Per person

cover image
avatar image

5.0

A day sailing in the fantastic Gulf of Trieste

Duration:

1 day - 0 nights

Italy:

Venice and the Gulf of Trieste

avatar image
avatar placeholder
avatar placeholder

+4 travellers

have booked

Starting from

€95

Per person

cover image
avatar image

5.0

Spring on Lake Garda

Duration:

1 day - 0 nights

Italy:

Lake Garda

avatar placeholder
avatar placeholder
avatar placeholder

+23 travellers

have booked

€99

Per person

cover image
avatar image

5.0

An all-inclusive day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

avatar placeholder
avatar placeholder
avatar placeholder

+3 travellers

have booked

€180

Per person

cover image
avatar image

4.8

Scopello, San Vito and Egadi: friends, good food sailing

Duration:

6 days - 7 nights

Italy:

Aegadian islands

avatar image
avatar placeholder
avatar placeholder

+10 travellers

have booked

€523

€550

Per person

cover image
avatar image

4.5

1 Week Professional Catamaran Training - Cagliari Sardinia

Duration:

7 days - 7 nights

Italy:

Southern Sardinia

Give this experience a try!

€1,320

Per person

cover image
avatar image
Intro sail Liguria

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€160

Per person

cover image
avatar image

4.9

Day on Lake Maggiore

Duration:

1 day - 0 nights

Italy:

Lake Maggiore

Give this experience a try!

€130

Per person

cover image
avatar image

5.0

Luxury sailing in the Gulf of Poets

Duration:

1 day - 0 nights

Italy:

Liguria

avatar image
avatar placeholder
avatar placeholder

+6 travellers

have booked

€90

Per person

cover image
avatar image

5.0

Day on a sailing boat

Duration:

1 day - 0 nights

Italy:

Liguria

Give this experience a try!

€100

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

10891 reviews

avatar placeholder

Luxury sailing in the Gulf of Poets

04/15/2024

Antonio C.

-

Italy

Giornata splendida, mare e barca perfetti, altissimo valore aggiunto l’equipaggio, simpatico gentile preparato ma soprattutto disponibile, e Costanza ottima cuoca, esperienza fantastica, da ripetere!!
avatar placeholder

Veleggiata verso il farò di Cecina con Aperitivo a bordo

04/11/2024

maurizio r.

-

Italy

Grazie per la bella domenica di relax in barca Maurizio e Giuliana
avatar image

Moorings and manoeuvres course - Night Navigation and Signals - Anchorages

04/10/2024

Stefano P.

-

Italy

Corso vela, efficace, utilissimo, sintetico essenziale in una parola strepitoso. Skipper istruttore preparato, simpatico ed all'altezza del ruolo.
avatar image

A weekend of sailing between Capraia and the island of Elba

03/20/2024

davide C.

-

Italy

Enrico è un comandante che sa mettervi a proprio agio in un equilibrio di libertà e professionalità . Se vi piace oltre al vento il buon cibo siete sulla barca giusta ..

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964