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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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5.0

Super!

Barcolana 58: 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

€280

Per person

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4.0

European Mile Builder - Leg 2: Gibraltar to Las Palmas

Atlantic islands: Canary Islands

6 days - 6 nights

One departure available

November

€660

Per person

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4.0

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

France: French Riviera and Porquerolles

6 days - 6 nights

One departure available

October

€550

Per person

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5.0

New

Cruise to the Golden Islands via the capes and bay of St Tropez

France: French Riviera and Porquerolles

5 days - 4 nights

27 departures available

February - October

Starting from

€595

Per person

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4.0

European Mile Builder: Leg 1 from Spain to Gibraltar

Spain: Andalusia

6 days - 6 nights

One departure available

September - October

€660

Per person

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4.8

Offshore and night navigation course on cabin cruisers

Italy: Tuscany

3 days - 2 nights

One departure available

October

€332

€299

Per person

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5.0

New

Basic and advanced sailing courses

Italy: Liguria

2 days - 1 night

4 departures available

October - November

€220

€198

Per person

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4.1

Corso di vela RYA Day Skipper Pratical sailing

Italy: Tuscany

4 days - 4 nights

12 departures available

October - December

€1,400

Per person

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4.5

School-holiday cruise from Marina di Pisa to Cagliari

Italy: Southern Sardinia

10 days - 10 nights

2 departures available

July

Starting from

€1,350

€1,282

Per person

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4.5

Relaxing weekend and sailing school

Italy: Tuscany

2 days - 1 night

3 departures available

September - October

€220

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

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

876 reviews

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Learn to sail in Liguria: First level sailing course

09/21/2026

Valentina G.

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IT

Orazio is an excellent skypper, helpful and attentive, he taught us a lot and we had fun! Highly recommended!

5-day itinerant cruise course

09/13/2026

Anne Claire R.

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DE

Fabienne is remarkable, educational, encouraging, attentive to everyone's needs, and allows everyone to take ownership of the boat and everything they want to learn. A great stay.
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Five days at the Pontine from Ostia - Sailing course and more!

09/8/2026

Giuseppe G.

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IT

This experience also included a sailing course. The skipper Enzo is an excellent instructor, competent, patient and always ready to involve the crew in steering the boat. We sailed a lot. The boat is well maintained, comfortable and clean. The dolphins also noticed it and accompanied us both in the navigation to Palmarola and in the one for the return to Ostia. Enzo knows the Pontine very well, we enjoyed the most beautiful coves without haste and always in safety. Also thanks to the favorable weather that gave us a beautiful relaxing but also active holiday for those who wanted to participate in the management of the boat during the numerous sailings.
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Five days at the Pontine from Ostia - Sailing course and more!

09/8/2026

Coretta P.

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IT

Beautiful holiday that I recommend to anyone who wants to experience the sea in the most intense and authentic way, with a discreet spirit of adaptation and a great desire to sail, learn and regenerate. Enzo proved to be a particularly professional, patient and prepared skipper, able to convey his experience by enriching every moment with many ideas and interesting topics. I sincerely thank all the crew for the fun and the many laughs shared!

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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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