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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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4.9

5-day sailing course: discovery and learning

France: French Riviera and Porquerolles

5 days - 4 nights

6 departures available

September - October

Starting from

€689

Per person

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4.0

European Mile Builder - Leg 7: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€635

Per person

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5.0

New

Sailing cruise to Nice: Estérel, bay of Cannes, Lérins Islands

France: French Riviera and Porquerolles

5 days - 4 nights

2 departures available

October

€595

Per person

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 - Sailing courses with skipper

870 reviews

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Cruise-Coastal Navigation Course Porquerolles-Calanque Cassis

08/24/2026

Didier R.

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CH

very nice trip in a very nice environment.
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Discovering the Argentario on a sailboat

08/23/2026

Paolo P.

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IT

[hidden] is a fantastic boat, very well distributed spaces, well organized, comfort truly remarkable for its length. But the plus was the skippers Arianna and Eleonora who throughout the holiday combined solid nautical skills, enthusiasm in transferring both seafaring and eco and ethological knowledge (especially on cetaceans), depth of thought, authentic sympathy and engaging cheerfulness.
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Cruise course in Sardinia

08/20/2026

Marta G.

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IT

Very nice experience. In addition to seeing wonderful places we had a great time. Throughout the week we found the ideal weather windy but not too much and allowed us to go sailing every day. The boats are not very big, we were 5 students plus the skipper for each boat (two boats in all) but in this way we could spend more time maneuvering and learn everyone. It is a basic course suitable even for those who have never been on a boat, but also very fun for those like me who had already been there. The holiday, and also the boats, are very rustic, we stayed every night sleeping in the bay at anchor, except one evening when we went to port in Bonifacio. The spaces are tight so you have to have a lot of spirit of adaptation but this also makes the holiday magical. For those who have never been on a boat I can say that it is like a camper on water. I recommend bringing a small rechargeable fan with USB (but that can go without power!), sometimes the evenings are a bit hot and not always so much air passes through the hatches. Although it was a course, the atmosphere was still relaxed, the skippers were very knowledgeable and we had a great time. Absolutely recommend.
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Learn to sail in a week in the Tuscan Archipelago

08/20/2026

cathy n.

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FR

First experience for us on a sailboat. We will keep wonderful memories of it. It was an incredible adventure! Thank you sincerely Marco for everything, we enjoyed it immensely.

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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.

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