Homepage cover
logo

Log in

Yacht sailing holidays & skippered tours in Italy

Discover more than 1 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

14418 reviews

avatar image

Sailing cruise to the Pontine: wonders a stone's throw from Rome

08/7/2026

Manuel C.

-

IT

The Pontine on an Old Style sailboat are pure magic. The skipper was impeccable: professional, attentive and able to make us experience the sea to the fullest, including delicious dishes, postcard anchorages and tender rides in the most evocative caves of Palmarola, the weather conditions did not allow sailing, but the skipper managed the navigation with professionalism, making every move safe and pleasant. Too bad that the travel company described this fantastic week with unfounded claims and criticisms. But the experience, thanks to the skipper and the places, remains truly special.

Sailing cruise to La Maddalena, Costa Smeralda and South Corsica - convenient Olbia embarkation

08/6/2026

Antonio C.

-

IT

Competent, experienced and helpful skipper. Comfortable and spacious boat. Costa Smeralda even more beautiful by boat. Unforgettable experience

Weekend on the island of Elba: among dolphins, enchanting bays and relaxation

08/6/2026

Daniela L.

-

IT

Beautiful experience! A mini holiday full of unique landscapes, nature and new friendships. For most of the trips, the wind gave us the opportunity to use the sails. It takes a bit of adaptation to sharing spaces, but with a few tricks everything becomes manageable. A weekend to remember! Thank you Salvatore, you have passed on your passion for the sea and sailing.

Discover the Egadi Paradise by sailboat from San Vito Lo Capo

08/6/2026

Nadia C.

-

IT

A bit disappointing experience. Somewhat restrictive rules on the boat (such as taking a shower before entering the cockpit after swimming), obligation to dine on land at least three evenings. The holiday begins on Sunday afternoon because on Saturday after boarding you are stopped, on Sunday you lose the morning shopping for the galley. It ends on Friday at lunchtime because we have to return to port, by motor, because we have to refuel. For the rest, a couple of evenings only in the roadstead and two beautiful sails. Extremely clean boat

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