header cover
sailsquare logo

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.

cover image
avatar image

5.0

Super!

Weekend sailing course from Bandol

France: French Riviera and Porquerolles

2 days - 1 night

16 departures available

July - October

Starting from

€300

Per person

cover image
avatar image

5.0

Let's sail together in Southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

2 departures available

June - July

€700

€665

Per person

cover image
avatar image

4.8

Super!

Midweek holiday on Elba and basic sailing course.

Italy: Tuscany

2 days - 2 nights

8 departures available

June - September

Starting from

€220

Per person

cover image
avatar image

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

cover image
avatar image

5.0

Super!

5-day sailing course: discovery and learning

France: French Riviera and Porquerolles

5 days - 4 nights

18 departures available

June - October

Starting from

€680

Per person

cover image
avatar image

5.0

Sailing in southern Sardinia

Italy: Southern Sardinia

6 days - 7 nights

5 departures available

July - August

Starting from

€900

Per person

cover image
avatar image
Weekend tra Versilia e Golfo dei Poeti

Italy: Tuscany

2 days - 2 nights

2 departures available

July

Starting from

€350

Per person

cover image
avatar image

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

cover image
avatar image

4.5

Holiday - School between the Tuscan Archipelago and North Corsica

Italy: Tuscany

6 days - 6 nights

2 departures available

August

Starting from

€750

Per person

cover image
avatar image

5.0

Learn to sail in a week in the Tuscan Archipelago

Italy: Tuscany

6 days - 6 nights

3 departures available

August

Starting from

€795

Per person

cover image
avatar image

5.0

Itinerant Coastal Cruise Training Course

France: Atlantic Coast

6 days - 5 nights

2 departures available

August

€830

Per person

cover image
avatar image

4.6

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

France: French Riviera and Porquerolles

4 days - 3 nights

One departure available

June - July

€480

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

816 reviews

avatar image

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

06/10/2025

Valentin U.

-

Switzerland

En seulement 4 jours, Cyril nous a appris une quantité impressionnante sur la navigation, les manoeuvres de voile et la vie sur un voilier en général. Sa pédagogie était bien adaptée à notre groupe qui se lançait dans cette aventure pour la première fois ; dès le départ, il nous a mis en confiance pour prendre les choses en main. Sa riche expérience de voyage au long court, qu'il partage volontiers, nous a d'autant plus motivé à poursuivre cet apprentissage. Merci Cyril!
avatar image

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

06/10/2025

Beryl B.

-

France

Merci à Cyril, nous avons fait un stage de voile de qualité, un chemin humble et réfléchi vers l’autonomie à voile et une vie à bord faite d’échanges, de respect mutuel et de convivialité !
avatar image

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

05/28/2025

Florent B.

-

France

Super stage! Merci Cyril pour ta pédagogie que ce soit sur la théorie ou bien les manœuvres. On se sent en confiance et tu amène progressivement le degré de difficulté cela permet de ne pas se sentir débordé. Accueil très convivial je recommande
avatar placeholder

Sailing course on the Côte d'Azur aboard a 15-metre sailboat

05/27/2025

JOHN B.

-

France

Cyril est un navigateur au grand cœur, quand on fait les choses avec amour cela porte ces fruits. La graine qui a été semé lors de ce stage a déjà germé et c est bien grâce à Cyril , [hidden] et mes chers coéquipiers de stage que je ne connaissais pas, merci à tous les 4.... Son expérience et ses anecdotes sont riches en enseignement. Ce stage navigation restera un souvenir précieux dans ma vie . Milles merci Cyril. Je recommande.

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

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.

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964