Homepage cover
logo

Log in

Yacht sailing holidays & skippered tours in Italy

Discover more than 2 sailing holidays in Italy. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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 - Yacht sailing holidays & skippered tours in Italy

13934 reviews

avatar image

A week sailing in the most beautiful places in the world

06/20/2026

Daniele M.

-

IT

It was a great holiday! We immediately felt like family. Giusy is a magician in the kitchen and Piero was an exceptional master skipper. The games in Burraco and Farkle have reached unattainable levels of competitiveness. It is difficult to describe in a few lines the whole week spent together, but we can say that they are 2 special people.

"Nel Blu dipinto di Blu" - midweek in Ponza, Palmarola and Ventotene

06/20/2026

Fabio F.

-

IT

Everything above expectations, beautiful islands, beautiful boat, exceptional captain. to be repeated absolutely.

Midweek relaxing in the Pontine Islands

06/20/2026

MARINA C.

-

IT

Thank you Mirko everything perfect!
avatar image

4 weekdays in the Pontine Islands

06/20/2026

simona s.

-

IT

Stefano is an excellent captain. Admired the mooring maneuver in Nettuno, not very easy. Also always calm, kind, nice. Even with the crew it went quite well. The only regret is almost always the engine, but it's no one's fault, especially if you have a busy schedule to respect because those who signed up want to do that. I need experience to understand that in the next short period I will look for only one Ponza, so you can choose the coves where to go according to where the wind blows and really sail. Until next time, Stefano

Customer Support

customer support

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!

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

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964