Homepage cover
logo

Log in

Yacht sailing holidays & skippered tours in Italy

Discover more than 8 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

14807 reviews

avatar image

Unforgettable adventure in the Aeolian Islands

08/27/2026

Daniele R.

-

IT

An unfortunately very negative experience caused by a truly endless series of problems with the boat, such as: - boat refrigerator not working and replaced with one of the dimensions absolutely not suitable to accommodate 7 people, - faulty alternator that did not allow the battery to be recharged during motor navigation with substantial problems for all the electrical instrumentation on board -Gas cylinder finished after 2 days of navigation severely limiting us in the preparation of meals, which following recharging had already proved to be partially discharged and therefore not refilled from the last charter -Too superficial cleaning of the boat since the last charter Added to this is the lack of prior communication of the skipper change, with a person who did not speak Italian and which made general communication difficult while sailing with us, the skippers of the other boats and the port insiders, this lack of prior communication is really incomprehensible, was there a fear that people would cancel the experience? We got to get to most of the islands, but we didn't get to visit them as it should have been, because most of the time we spent in the ports fixing boat problems or waiting for technicians to do it. I think it would have been right for Gaetano to recognize and take responsibility for these inconveniences by reimbursing us at least part of the fee paid for this (non) holiday, instead he has always minimized every issue by demonstrating little intellectual honesty and little care of his customers. Unfortunately, a mention must also be made of Sailsquare, which, aware of the situation we were facing, left us at the mercy of the problems without offering us concrete and valid support. I leave only 3 stars to the destination because in fact we saw and enjoyed it very little, 1 star with our eyes closed for the skipper and the boat. Too bad.

Amazing Pontine Islands on a sailing boat

08/27/2026

Rita G.

-

IT

We spent 3 wonderful and unforgettable days. Carlo is a very good skipper with a great deal of experience and a lot of passion for sailing.
avatar image

Magical Pontine: full sail to discover the archipelago

08/27/2026

Enrico V.

-

IT

I would say that the experience did not go badly but my expectations were a little higher. The crew was excellent company and a nice group was created that was able to manage all the various difficult situations in the best possible way.
avatar image

Sailing in a trimaran to the rhythm of the wind

08/27/2026

gloria c.

-

IT

We had a great time, the skipper super attentive, very accurate and competent, very didactic experience, nothing to say, advice to all those who want to experience sailing because you can touch it with your hand

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