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

14790 reviews

Sardinia and Corsica on comfortable 15-metre boat with private bathroom in cabin

08/26/2026

David P.

-

FR

An exceptional experience on Andrea and Sarah's boat! A very well equipped boat; skippers who know the region like the back of their hand and who take us to the best places at the best times. In addition, they create a relaxed, serene and friendly atmosphere on their boat. We spent a week of happiness with our family with our 2 children (4 and 8 years old) and recommend with our eyes closed!
avatar image

Aeolian Islands: between sea and authentic flavours

08/26/2026

Emanuele O.

-

IT

Fantastic experience, first time sailing for a week and it was very enjoyable. The charm and landscapes of the Aeolian Islands certainly make the difference. We sailed with the skipper Carlo, experienced and competent. Unfortunately, due to the low wind, we only sailed once. But this does not depend on anyone. Definitely recommended experience and that I would do again.

The Mediterranean Flotilla: Capri, Ischia, Procida and the Pontine Islands - ONLY MEN SEATS

08/26/2026

Anna M.

-

IT

The experience overall was positive as a good atmosphere was created on board among the participants. However, there were several aspects that did not satisfy me and for which I do not think I will book another trip with Sailsquare, much less with the organizer LAFLOTTIGLIA.IT. First of all, I was looking for a flotilla experience, which for what was my knowledge of the term, meant a sailing cruise with a significant number of boats. My expectation was 5-6 boats, not 3. I had chosen this package because I had already had an experience with 3 boats and I was looking for something more aggregating, with greater participation. This aspect unfortunately combined with the fact that, despite some offer from the skipper to join another boat, most of the time they spent their time alone. We have also heard rumors from other participants of a misalignment between skippers that may have influenced the aggregation. Another negative aspect concerns the fact that the organizer LAFLOTTIGLIA.IT created the Whatsapp group, then disappeared. I tried to contact him by phone and via whatsapp and, despite the constant views of group chats, he did not consider it necessary to respond to one of his customers. The first night on the boat was traumatic for all the participants as it was impossible to fall asleep due to the very high presence of mosquitoes, due to the lack of disinfestation of a river near the Marina of Castellammare di Stabia. For weather reasons, we spent the first night in this marina and, since the last night in the marina (Friday evening) was scheduled in the program, we decided (all the participants of the 3 boats without exception) to find an alternative accommodation for that last night which, I repeat, was scheduled to be spent on the boat. I personally asked the organizer LAFLOTTIGLIA.IT and Sailsquare to recognize us a contribution for the night in the hotel that we paid for as we believed that the conditions offered by the organization, well aware of the situation in the marina, were not acceptable and that it was not correct to postpone the matter to a "simple presence of mosquitoes foreseeable on a sailing trip", This response, received by Sailsquare and not by the organizer as it was not reachable, was not considered acceptable as the incident was anything but ordinary. It also seemed to us a very unsmart choice, commercially speaking, reputationally, not to meet us as the conditions of the marina were certainly known to the organizer, therefore, if the organizer consciously chooses to have his passengers/travelers face this discomfort (I'm not talking about the first night but the last one that was scheduled in the program), something makes me think that he had a convenience starting from that marina. As for our skipper, I have no particular comments to make, he was a helpful and friendly person even if there were some communication problems during the holiday, specifically when we were talking about the itinerary to follow or the options available for the day / evening, which were always resolved peacefully although with tones sometimes a little too "heated" for my standards.
avatar image

A week with friends in the Pontine Mountains - embarkation from Procida

08/26/2026

Martina M.

-

IT

A truly unforgettable week on the boat! Much of the credit goes to our skipper Umberto who immediately managed to put us at ease with his sympathy, availability and professionalism. He was much more than just a skipper: always present, attentive to our needs and able to create a special atmosphere on board, making us feel immediately at home. A special mention also goes to his skills as a chef! He delighted us with really delicious dishes, prepared with care and passion. Thanks to him we experienced a week of sea, relaxation, laughter, good food and many moments that we will take with us. An exceptional skipper, a special person and... Not a bad chef! If we were to leave tomorrow, we would have no doubts about who to choose!

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