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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

Super!

Crociera Scuola in Costa Azzurra isole Lerins

Italy: Liguria

6 days - 7 nights

2 departures available

August

Starting from

€750

Per person

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4.8

Super!

Midweek holiday on Elba and basic sailing course.

Italy: Tuscany

2 days - 2 nights

One departure available

September

€220

Per person

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4.9

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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4.8

Super!

Introductory sailing course

Italy: Liguria

2 days - 1 night

One departure available

September

€260

Per person

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5.0

5-day sailing course: discovery and learning

France: French Riviera and Porquerolles

5 days - 4 nights

7 departures available

September - October

€680

Per person

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5.0

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

2 departures available

August - October

Starting from

€559

Per person

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4.5

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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4.5

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

Spain: Galicia

6 days - 6 nights

One departure available

September

€470

Per person

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4.5

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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4.5

European Offshore Mile Builder - Leg 1: Hamble to La Rochelle

France: Atlantic Coast

7 days - 6 nights

One departure available

August

€470

Per person

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4.5

European Offshore Mile Builder - Leg 1: Bay of Biscay Crossing

Spain: Galicia

9 days - 9 nights

One departure available

September

€875

Per person

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4.5

Holiday - School between the Tuscan Archipelago and North Corsica

Italy: Tuscany

6 days - 6 nights

One departure available

August

€750

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

826 reviews

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5-day sailing course: discovery and learning

08/16/2025

Patrizia B.

-

Italy

Good morning Cleaning the boat.. including furniture the last day was not planned but we had to do it! Even we team have always kept clean and tidy every day ... and in addition when I arrived the first day inside the boat was not clean ..
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5-day sailing course: discovery and learning

08/16/2025

Adonis S.

-

France

First sailing experience. It was very nice! With friends. We learned a lot about sailing at sea and how to handle the boat. But also, we went to some very beautiful places in the Var, so you can't ask for more. This first course makes you want to embark on another sailing adventure!
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Midweek holiday on Elba and basic sailing course.

08/13/2025

Manuela T.

-

Italy

Experience as described, too bad we had 2 days of zero wind so no sailing and even the training was almost nil, but this could not be predicted. Beautiful places, beaches and water. The boat is spartan, as you can see in the photo, but comfortable, in my opinion it is better to rent it whole with people you know. I didn't get along well with the skipper, but it's a personal matter (not all characters are taken). The final bill of extra expenses, in my opinion, was not totally crystal clear. I had fun with my family, I took fantastic baths in equally beautiful coves. So overall it was a positive experience.
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Southern Brittany: 7-Day Catamaran stage from La Rochelle

08/11/2025

Giovanni T.

-

Italy

all very good

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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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