Week long to 1 day sailing courses with skipper

Week long to 1 day sailing courses with skipper

Have you always dreamed of hoisting the mainsail and learning to steer? Embark on the boat of a professional skipper who will be delighted to share with you their passion for sailing. Whether you are a beginner or an experienced sailor, a novice or a passionate sailor, set sail and sharpen your sailing skills in Greece, Croatia, Spain, Italy, and across the world.

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Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Discover who’s already onboard

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

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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!

Reviews - Week long to 1 day sailing courses with skipper

691 reviews
20 / 10
Maurizio R.

Maurizio R.

review about Corso Ola Regata at the Marina di Salivoli: sports weekend November 2022

10 / 10
Great Stephen, regatta course in the pouring rain with sea formed and "barrel" from 30 knots of wind. I believe that only in this way can we really learn to navigate. All this always and in any case in safety and under his supervision. Thanks also to Germano who guided us for the regatta we did the next day (this time under the sun). Great staff
Luca T.

Luca T.

review about SAGRA DEL TOTANO: Offshore sailing course with professional skipper Riccardo October 2022

10 / 10
Riccardo is an incredible skipper, both for his experience and competence and for his ability to put all the crew members at ease and create a family and friendly atmosphere. During the 4 days of the course we learned a lot without ever feeling the fatigue of learning, but we also confronted and had fun for the duration of the experience. I highly recommend it, experience certainly to be repeated.
Markus K.

Markus K.

review about The 54th Barcolana in company October 2022

10 / 10
Hello Mark, it was a really nice weekend, you were very good and nice. Maybe if next year you do it again, I will gladly return. Dear Greetings
Francesco G.

Francesco G.

review about Corfu and Diapontie starting from Santa Maria di Leuca August 2022

10 / 10
Skipper from 10 and praise, very prepared, nice and helpful. Fun holiday, we visited beautiful and characteristic places. Spectacular crew. As soon as you get on board you immediately notice the professionalism and deep knowledge of the navigation area of The commander Fra! Skipper and holiday highly recommended!!! Hello and to the next adventure commander Fra!
Pierre D.

Pierre D.

review about Pierre's holidays in Brittany July 2022

10 / 10
Thank you Benoît for these 3 days around the islands of Groix, beautiful island and Houat! We had a great time with you on your boat. The anchorage of beautiful island, swimming on the island of Houat and dolphins on the way back to Lorient leave us wonderful memories of our getaway in Brittany. We loved your coffees and dark chocolate! The boat is great to helm and fast... Besides, I don't think another boat has overtaken us! Beautiful season to you! Pierre - Eric and the children
Veronica D.

Veronica D.

review about Formentera and Ibiza June 2022

10 / 10
Going boating with Tommaso is an experience. In addition to being an excellent skipper and 'also available for excursions and out of program .. A holiday dedicated to the sea and culture. To be repeated absolutely !!!
Emanuele C.

Emanuele C.

review about Offshore navigation 370 nm. Sicily / Sardinia Nautical Education Vacation May 2022

10 / 10
Unique experience and amazing people! A trip full of emotions and that I will never forget, Marco and Valentina welcomed me on the boat, and immediately made me feel at home. During the three days of travel I had the pleasure of getting to know them better. Marco is a calm and kind person, a super competent and professional skipper. Always willing to teach his crew how to fix the course and sails, regardless of the level of experience. Master of sailing and unique life. Valentina, also very kind, is a bomb of energy and happiness, always ready to entertain and spoil the crew with aperitifs and delicious dishes. I will never forget the crossing of the Tyrrhenian Sea. Between naps tickled by the waves of the sea, aperitifs with traditional food and white wine, and shifts at the command during which to learn to manage the boat. And finally, three days of pure relaxation and fun in Sardinia immersed in unique coves with emerald water.
Sid K.

Sid K.

review about Sail to discover the Breton coast and its islands from Saint-Malo April 2022

10 / 10
What to say, except that everything was perfect! And honestly I'm not exaggerating. Jean Luc was kind enough to share his passion for sailing with us and he made us discover his little secrets of navigation, wonderful places, his little dishes .... His benevolence, his professionalism, his ability to adapt, his daily good mood, his patience, his adaptability ... (the qualifiers are numerous) allow a daily fluidity. he knew how to put himself at the level of each of us. We took pleasure in exchanging around sailing, but his playground is much larger, he knows small anchorages away from the crowds, the islands, the sea and the coast have no secrets for him. He managed to get the mayonnaise to take with the whole crew. Jean Luc for all this Chrystelle and I thank you for the excellent moment you offered us.
Spartaco M.

Spartaco M.

review about CrazySail Skipper Academy Lite: Punta Ala - April 30th April 2022

10 / 10
Great Inti! The most ''ganzo'' skipper (tuscan like me) I have met so far. Really engaging and dynamic person from a human point of view, but technical at the same time in pointing out some dangerous situations to the skipper or helmsman on duty, always with a smile or a joke that does not hurt. I hope to have the opportunity to sail with you again Good wind and see you soon
Francesco Maria V.

Francesco Maria V.

review about CrazySail Skipper Academy Lite: Lake Garda - April 9th April 2022

10 / 10
Matteo was the skipper of a day on Lake Garda, a precise and helpful attentive person, with the joke ready even in more complicated situations. I recommend it for your raids at sea!
Sandra K.

Sandra K.

review about Sailing course in the Grenadines March 2022

8 / 10
I guess the communication was the biggest issue, despite speaking some English relaying information back was poorly executed by the skipper, which have cost me my flight, some lack of empathy during hiking trips instead of allowing time to rest he was pushing for faster or take the bus. Speaking French round the table despite 2 people not speaking the language out of 4 was little rude, otherwise he was very caring when I was unwell during sailing at times and provided effective medical solution, The trip however was a blast, beautiful islands and locals with packed activities, and amazing memories to remember. ---------------------- SKIPPER ------------------------------ Hello Sandra, I'm really sorry that the cruise you booked didn't live up to your expectations. I did everything I could to create a good atmosphere on board, even with a mixed crew speaking different languages. The holidays you booked were a sailing course where you had to travel several kilometers. My goal was to transmit the passion and rudiments of sailing. For an itinerary that includes the Grenadines Islands, there are many hours to devote to navigation.
Mareike J.

Mareike J.

review about Sailing in winter - Offshore sailing March 2022

10 / 10
Barbara and Claudio are great hosts who made me feel home and free on their boat. They are speaking an excellent English so even for me as the only non-Italian it was easy to have conversations with them and to learn the English nautic language. It was so great to listen to their sailing experience all over the world. In general they are very caring and uncomplicated hosts, so not only my English was not a problem they also took care of eating habits. Barbara is a fantastic cook, and I garantee you definitely won`t lose weight on the boat but it will be worth it. The communication before the trip was very easy and and made you feel welcome already. They also were very supportive in terms of arrival and departure. The boat was beautiful and comfortable. In short, two truely exceptional great humans with a wonderful boat in a beautiful location!
Elena F.

Elena F.

review about 2021 Marina di Loano Winter Championship October 2021

10 / 10
Alberto and his dad were very kind and helpful. They are passionate and experienced! They involved us in the regatta (we also positioned ourselves well), it was a very positive, exciting, absolutely recommended experience. The boat is comfortable and the port of Loano close to the village center and the beach.
Maddalena G.

Maddalena G.

review about Sailing lessons on a cruise in the Flegrean islands August 2021

10 / 10
The holiday I was looking for! Beyond the tour that we managed to do, touching Ischia, Procida and Amalfi (which is worth visiting) what I have left most is the passion and the will of Eugenio to appreciate life on the boat for what it is ... team spirit, organization, collaboration. he is really very prepared, precise, patient and available to make you participate in the navigation. I was so comfortable on the boat and with the rest of the crew, that I didn't even feel the need to get off to visit when we were stopped in port. It was an experience that opened me up to a world I didn't know. it has enriched me so much on a human level. Eugenio and Anna (his partner) were two excellent travel companions.
Andrea G.

Andrea G.

review about Let's learn how to sail a boat August 2021

10 / 10
Professional of the sea, expert navigator, precise and punctual. Excellent teamwork with his wife in the all-round organization of the perfect holiday. Nice entertainer who shares his browsing and life experiences. The boat is masterfully kept and nothing is missing on board. Keep it up Giò!
Vincenzo M.

Vincenzo M.

review about Wandering around Southern Sardinia July 2021

10 / 10
we have just disembarked from a week experience with the Havana Vela team (Giampy and Edo)... what to say... important, comfortable and performing means. Excellent skipper, really with great experience... not only skipper.. but really a member of the group with sympathy, availability, without ever losing professionalism .... a week full of smiles, sympathy, unique sailing experience! Unique experience... more than recommended...
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XX reasons to choose Sailsquare for you next TRAVEL IDEA

  • Find the adventure of your dreams from hundreds of sailing courses - with prices starting at €150 for weekends and €400 for week long trips.
  • Find your skipper from a community of several thousand local skippers driven by the desire to make you discover their passion for sailing and their sailing area.
  • Learn to sail while exploring magical places - only accessible by boat.
  • Share the magic of life aboard a sailboat with the other crew members.
  • Choose the experience that best suits your objectives, whether you are a total beginner or an expert.
  • Enjoy extraordinary experiences and realise your travel dreams - such as a transatlantic crossing, or Spitsbergen cruise. Or, if you prefer, participate in internationally renowned regattas - such as Antibes, Saint Tropez.
  • Sail all year round in more than 95 destinations across all the seas of the world: the Caribbean, Mediterranean, Pacific, Indian and even Greenland or Patagonia!

Tips to help you to better plan for your next sailing course or regatta holiday:

All you need to know about your next sailing cruise.

Learning to sail: how much does it cost?

You can find sailing courses from €150 on weekends and €400 on weekdays. This amount then varies according to several parameters such as the destination, style of the boat and proposed itinerary. Like with any other such experience, the cost of transport to and from the sailing trip, the participation in the ship's cash float (often around €150 per week), as well as the extras during your cruise, such as meals out.

The best destinations for an adult sailing course

Each destination is different and therefore so too are the possibilities. For a weekend sailing course, there is availability in more northern European destinations such as France - including Brittany, the French Riviera, the Atlantic coast. Across the Mediterranean, several areas are particularly well suited for a one-week sailing course: Croatia, the Greek Cyclades, the Balearic Islands, Corsica and Sardinia. For those who wish to combine learning to sail with the sun of the tropics, fly to the Caribbean Sea and sail in the paradise islands of the Grenadines or Guadeloupe.

I am a beginner - I am a pro. Is there an experience for me?

If you have never sailed before and would like to discover this new feeling, we recommend that you head for a discovery trip where you can learn how to steer, hoist, and handle the sails. For those who wish to improve their knowledge - including cartography, meteorology, night navigation, spinnaker, radios - recommend that you go on more technical and longer sailing courses (1 week or more) that will allow you to fully immerse yourself in the manoeuvres and life on board. For the more adventurous, cross the Channel, the Atlantic or the Mediterranean!

Sailing internship: Finally make your dream of learning to sail come true

There are dreams that can now be easily realised - learning to sail is part of it! No special knowledge is required to start sailing with a professional skipper who will gradually transmit his passion and advice to you during sailing courses corresponding to your level. Get ready to share unique experiences with other crew members and enjoy the friendliness of living on board a sailboat.

Courses & regatta: best destinations

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