Sailsquare | N°1 in Europe for sailing and catamaran holidays

Matteo R.

Provider type:

Organisation

City:

Parma

Member since:

2015

2483 Sailsquare travellers have been on board my experiences

My experiences

4.8

Squid Festival: let's close the season on a high note! - on board a 17mt boat

Italy: Tuscany

2 days - 2 nights

2 departures available

October - November

€300

Per person

4.8

Vacanza a piedi nudi: Weekend tra Elba e Capraia su barca 15m

Italy: Tuscany

2 days - 2 nights

2 departures available

September - October

Starting from

€240

Per person

4.8

Barefoot holiday: Weekend on Elba on a 17m boat

Italy: Tuscany

2 days - 2 nights

2 departures available

September - October

Starting from

€260

Per person

Gallery

20+

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About us

"I like sailing, it allows me to live a dimension that suits my personality", I also like to do fest, in my holidays I don't need antidepressants or mineral salts but white wine and anchovies. See you on board!

My sailing areas

Tuscany

Italy

Northern Sardinia

Italy

Corsica

France

Liguria

Italy

Tuscany

Italy

Northern Sardinia

Italy

Corsica

France

Liguria

Italy

My boats

Type

Sailboat

Length

16 m.

Toilets

Cabins

11+

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Travel with peace of mind

Total transparency

Want to avoid surprises? Find out before you book who your skipper and fellow travellers will be. Do you have questions or doubts? Send a message to the skipper!

Flexible cancellation

Cancel within 30 days of departure for any reason and receive a full refund. Want even more? Purchase the extension to cancel your booking until your departure.

Constant support

Our dedicated multilingual support team is always ready to assist you, before and during your holiday, and is always in touch with the skippers we work with.

Reviews

4.8/5

out of

224

reviews

Skipper

Boat

Destination

Vacanza a piedi nudi: Weekend tra Elba e Capraia su barca 15m

09/10/2025

Stefania D.

Italy

Perfect weekend! On the boat with us was the skipper Sergio, who made the weekend more than enjoyable. Always available to answer our questions and curiosities, able to choose the ideal route to be able to also afford sailing. The group then did the rest. All ready to lend a hand and get involved. It was the first time on a sailing boat and the weekend went far beyond expectations

Vacation between Tuscany and Corsica on a magnificent 17m boat

09/8/2025

Giuliana C.

Italy

Good morning, the weather according to the skipper did not allow me to get to Corsica, so I saw places that I already knew, The skipper presented himself very well initially and then disappointed more and more every day. Fortunately I made friends with some of the guests and this lightened the situation.

Corsica and Tuscany in flotilla, boats of 16 and 17 meters.

09/3/2025

David B.

Italy

Matteo is a very very competent, helpful and kind person. Without adding who knows what speeches, he is a person who can be totally trusted and with whom it is a pleasure to navigate. I can only recommend him, I will definitely return to the sea with him. Thank you!

Corsica and Tuscany in flotilla, boats of 16 and 17 meters.

09/2/2025

Annalisa M.

Italy

Very fun and engaging experience, unfortunately due to bad weather we could not make the crossing to get to Corsica and we stayed near the Island of Elba and Capraia. However, despite this inconvenience, the balance of the holiday was very positive, the group was well assorted and the skipper was very kind and helpful towards our needs. I therefore recommend Matteo and his team if you intend to make an unforgettable trip on a sailing boat.