header cover

Courses & regatta yacht sailing holidays & tours in Italy

Discover more than 14 opportunities to get on board a Courses & regatta adventure in Italy. A unique experience with a local skipper, starting at €350 a week.

14

experiences

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 - Courses & regatta yacht sailing holidays & tours in Italy

527 reviews

avatar image

A weekend of sailing between Capraia and the island of Elba

04/24/2024

Angelo C.

-

Italy

Bellissima esperienza, bella gente con uno skipper top!
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 ..
avatar image

From the AEOLIAN to the PONTINE - Adventure, Navigation and Relaxation - One Way

09/29/2023

Maya P.

-

Italy

Professionalità simpatia serietà ma soprattutto un insegnante fantastico: chiarezza, disponibilità, e conoscenza trasmesse in ogni istante con spontanea semplicità con al primo posto sempre la sicurezza di tutti. Grazie cercavo una vacanza scuola me la immaginavo proprio così. Oggi mi porto a casa molte nozioni interessanti che non vedo l’ora di mettere in pratica di nuovo e approfondire, ma anche tanto relax e un soffio di vento nei capelli ??????????????????????

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!

Italy: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaAmerican ExpressApple pay

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