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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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4.8

Super!

Introductory sailing course

Italy: Liguria

2 days - 1 night

One departure available

September

€260

Per person

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4.8

Super!

Offshore and Night Navigation Course between Elba, Corsica and Capraia

Italy: Tuscany

3 days - 3 nights

2 departures available

October - November

€299

Per person

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5.0

5-day sailing course: discovery and learning

France: French Riviera and Porquerolles

5 days - 4 nights

5 departures available

September - October

€680

Per person

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4.3

European Offshore Mile Builder - Leg 5: St Tropez to Malta

France: French Riviera and Porquerolles

6 days - 6 nights

One departure available

October

€470

Per person

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5.0

Weekend sailing course from Bandol

France: French Riviera and Porquerolles

2 days - 1 night

6 departures available

September - October

€300

Per person

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4.3

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€470

Per person

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4.3

European Mile Builder: Leg 1 from Spain to Gibraltar

Spain: Andalusia

6 days - 6 nights

One departure available

September - October

€470

Per person

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4.7

Southern Brittany: 7-Day Catamaran stage from La Rochelle

France: Brittany and Normandy

7 days - 7 nights

4 departures available

September - October

Starting from

€1,431

Per person

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4.6

Barcolana - Mini-cruise to Trieste to see the regatta from the Sea

Italy: Venice and the Gulf of Trieste

2 days - 2 nights

One departure available

October

€371

Per person

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4.2

Weekend of theoretical and practical course

Italy: Liguria

2 days - 1 night

7 departures available

October - November

€250

Per person

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Barcolana 57: a day at the most famous regatta in the world

Italy: Venice and the Gulf of Trieste

1 day - 1 night

One departure available

October

€247

Per person

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5.0

Approach to sailing: day on a boat with sailing lesson

Italy: Tuscany

1 day - 0 nights

2 departures available

October

Starting from

€97

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

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

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 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

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

837 reviews

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European Offshore Mile Builder - Leg 2: from La Rochelle to A Coruña

09/9/2025

ivan l.

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Slovenia

Real experience, very usefull
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Midweek holiday on Elba and basic sailing course.

09/8/2025

Massimiliano F.

-

Italy

Experience in line with our expectations aimed at learning sailing on a sailboat, anchoring in the roadstead and landing in port. Ivo was able to be a good skipper, encouraging us to try and make mistakes (recovering us with his decisive action) and reassuring us when the adverse sea weather conditions of the first crossing put us to the test. We spent some pleasant time chatting, cooking and relaxing in the roadstead, but also visited Porto Azzurro with a dinner in the village and a pleasant morning walk to discover the area. The stop in the Stella gulf for a nice swim and a swim to reach the beach is also very pleasant. They were really 4 interesting, informative and relaxing days that we recommend to those who, like us, do not want to just stay sunbathing.
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Learn to sail in a week in the Tuscan Archipelago

09/1/2025

Alessio M.

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Switzerland

I was really looking forward to the sailing week in advance and my expectations were fully met. We sailed around the island of Elba, spent the night in beautiful bays, jumped directly from the ship into the sea, snorkeled on rocks and cooked together on board in the evening. A special highlight was that we caught fresh fish and cooked it the same evening. We saw dolphins jumping out of the water. On the island of Elba we were able to discover the landscapes and eat fine fish. The sunrises and sunsets were fantastic, and also to feel the stormy wind on your skin as well as the high waves breaking on the rocks was an impressive experience. Equally unforgettable was the clear starry sky over the sea. The ship was very well equipped with running water, electricity and comfortable beds in which you were gently lulled to sleep by the rocking of the sea. I would like to highlight our skipper Marco. He knows the island of Elba very well, always knew the best places to stay, had a sure sense of weather and waves and always made the right decisions for the entire crew. We learned a lot from him, about sailing, about wind and weather, about nature, history, technology and also about ourselves and the people on board. All in all, it was a great experience. I am very happy, full of beautiful memories and would sail again at any time.
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Itinerant Coastal Cruise Training Course

09/1/2025

Fabrice V.

-

France

I spent an excellent week of coastal navigation training aboard [hidden], a beautiful sailboat that is very pleasant to live in and handle. Our meeting with Fabienne was a very nice meeting. Passionate about sailing without a doubt, you can feel her passion for passing on her knowledge and her great experience in the field from day one. I was impressed by his ability to listen and adapt to everyone's level. His calmness, his benevolence, his natural authority and his pedagogy are the best assets to gain confidence, consolidate his achievements and improve his skills with the concern for safety at sea. Observe, anticipate, take into account the signs, do not take risks... Perfect organization of life on board and sailing with a crew where everyone found their place, rotating on the different stations. We shared many convivial moments, evening discussions and laughed a lot. Fabienne is a very endearing person, I will gladly return to sail with her.

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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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