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Yacht sailing holidays & skippered tours in Canary Islands

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.

  • Sailing Holidays
  • Atlantic islands
  • Canary Islands

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • 5 reviews

    Around Lanzarote and La Graciosa

    from 1 April - 7 nights
    Canary Islands Atlantic islands
    2 people interested
    in this holiday
    669€ Per person
  • 5 reviews

    Around Lanzarote and La Graciosa

    from 8 April - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    669€ Per person
  • 5 reviews

    Around Lanzarote and La Graciosa

    from 15 April - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    669€ Per person
  • 5 reviews

    Around Lanzarote and La Graciosa

    from 22 April - 7 nights
    Canary Islands Atlantic islands
    1 person interested
    in this holiday
    669€ Per person
  • 5 reviews

    Around Lanzarote and La Graciosa

    from 7 May - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    669€ Per person
  • 5 reviews

    Around Lanzarote and La Graciosa

    from 14 May - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    669€ Per person
  • 5 reviews

    Around Lanzarote and La Graciosa

    from 21 May - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    669€ Per person
  • 5 reviews

    4 days around Lanzarote

    from 3 October - 3 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    424€ Per person
  • 2 reviews
    almost
    confirmed

    1 week professional catamaran training - Marina San Miguel - Tenerife

    from 18 November - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    1.479€ Per person
  • 2 reviews
    almost
    confirmed

    1 week professional catamaran training - Marina San Miguel - Tenerife

    from 25 November - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    1.479€ Per person
  • 2 reviews
    almost
    confirmed

    1 week professional catamaran training - Marina San Miguel - Tenerife

    from 2 December - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    1.479€ Per person
  • 2 reviews
    almost
    confirmed

    1 week professional catamaran training - Marina San Miguel - Tenerife

    from 9 December - 7 nights
    Canary Islands Atlantic islands
    Join in on this experience!
    1.479€ Per person
  • 1
  • 2

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Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.

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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!

Reviews - Yacht sailing holidays & skippered tours in Canary Islands

60 reviews
20 / 10
Nicoletta G.

Nicoletta G.

review about welcome new year !! December 2021

10 / 10
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.
Giorgio N.

Giorgio N.

review about Vacation on a luxury catamaran in Tenerife February 2020

8 / 10
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.
Antonio P.

Antonio P.

review about The beauty of the Canary Islands in summer August 2019

10 / 10
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!
ALESSANDRA G.

ALESSANDRA G.

review about From Tenerife to La Gomera and La Palma July 2019

10 / 10
Our holiday in the Canary Islands was wonderful! Ben, in addition to being a beautiful person, is a magnificent, pleasant and very competent skipper!
Paola G.

Paola G.

review about Among Sky, Sea Volcanoes and Trekking in Tenerife. Week of sailing - All Inclusive. January 2019

10 / 10
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
Sara V.

Sara V.

review about Lanzarote in sailing catamaran February 2019

10 / 10
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!
Giulia R.

Giulia R.

review about New Year's Eve to discover the Canaries December 2018

10 / 10
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
Daniele M.

Daniele M.

review about Spend the summer under the sun of the Canary Islands August 2018

10 / 10
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!
Alessandro F.

Alessandro F.

review about Tenerife, the sea in winter on board a 61-foot yacht! January 2018

10 / 10
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!
Giuseppe B.

Giuseppe B.

review about New Year's Eve on a catamaran among volcanoes and trade winds December 2017

10 / 10
Very good both as a skipper and as a travel companion. Very attentive to the crew and the boat. I would do more holidays with him again!
Andrea A.

Andrea A.

review about Canary mon amour - New Year on a sailing boat December 2017

10 / 10
Prepared person and excellent skipper, nice and sociable. has created the right harmony on holiday by uniting everyone's needs.
Nycolas M.

Nycolas M.

review about Tenerife, winter sea boarding a 61-foot yacht! November 2017

10 / 10
Marino and Federica were formidable!! Marino is an excellent sailor who will make you feel good throughout your stay. Beautiful week!!! Thanks again!
Donatella P.

Donatella P.

review about Lanzarote between art and nature Fuerteventura and Tenerife with a touch of sophistication! November 2016

10 / 10
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 !!!!!
Mario C.

Mario C.

review about The ocean is calling you (all inclusive) August 2016

8 / 10
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!
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