Yacht sailing holidays & skippered tours in Canary Islands
Sun, sailing and all kinds of sporting activities: embark with a
local skipper for an exceptional a local skipper for an exceptional
sailing holiday in the Canary Islands. Canary Islands. Discover
this superb archipelago from the sea to enjoy its beauty to the
full.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
It was an unforgettable experience. We sailed meeting dolphins whales tuna. We wanted to sail and Michele is also a great navigator. A climate of collaboration was immediately created on board. Michele is very generous and without problems made us do the maneuvers. Unfortunately the first days there was not much wind, we sailed by motor but on the other hand we enjoyed the beautiful sunsets in navigation. Thanks Michele .... Until next time.
The week training is very useful. Jos is a quite relaxed teacher that lets you sail and manouver the boat most of the time. The organization of the holiday and training is not perfectly clear, but that lets space for the crew to decide part of it.
Perfect vacation
Dennis tries always to find the best solution based on the wind and hosts needs
We’ve Spento a wonderful week with the boat, fully equipped and in the nices views
And he likes to prepare good espresso coffee!
When you're on board MITITI
you don't need additional invitations
Everything runs as smooth as oil
here we grow just the grass I want!
Everything is perfect on board MITITI
If you like to sail DO NOT linger
and choose Filippo
Perfect holiday to discover the imposing marine and terrestrial nature of Lanzarote and the enchanting remote Graciosa, on board a light and comfortable catamaran like a small house without walls that comes alive with agility to the breath of the wind of the trade winds and safely sails the ocean wave! Great company and harmony with the crew members and so much to learn from an experienced and enthusiastic skipper!
Alessandro is an exceptional skipper, as well as an extremely pleasant person with whom to share the trip! Perfect holiday for an alternative New Year's Eve, highly recommended.
See you next Ale, thanks again for everything!!
Giulia and Zac
Despite being very young, Vitaliy is already a very experienced skipper. I felt sure in every moment of the week and I enjoyed sailing together. Canary islands can be tricky because of the changing wind, Vitaly put our security at the first place and decided to spend the nights in marinas instead of anchoring roadstead. In the canary island the distance between the islands is considerable, so there were many occasions to sail but also a relevant amount of motoring, in order to get to next island in a reasonable time. I would for sure join Vitaliy for another sailing holiday!
Fantastic week, aboard a dream boat. Fabio, an experienced and capable skipper, made my wife and me live a pleasant and relaxing holiday. I will certainly go back to sailing with him!
5-star holiday !!!! The itinerary agreed together in detail was very interesting. Of course we fell in love with the Canary Islands, especially Lanzarote. Paolo and Cecilia's boat is a very respectable boat, very comfortable and safe. Captain Paolo's experience made us always feel safe and enjoy the majesty of the great ocean, which sometimes put a strain on our stomach. And what about Cecilia's welcome and gourmet pampering.... great cook ? Thank you and good wind for all your oceans !!!!!
Comfortable and solid boat very maneuverable. Andrea a welcoming, confident host, with a great desire to sail and able to satisfy any request for shore excursions. If you like the wind they are the right islands!
