Learning How To Sail a Catamaran, 10 Ways To Save Money and Time

Most people believe there is only one way to learn how to sail. In this article, I will show you ten creative ways of learning how to sail a catamaran or a sailboat.

The old times where you had to attend a formal sailing school and have your own boat are gone, all you need nowadays are some willpower and an internet connection, of course, sooner or later you will have to get out on a boat and actually practice.

Still, nowadays, much of the theoretical stuff can be learned through alternative ways; this is both much cheaper and usually more efficient.

1. Cruise and Learn

Cruise and learn is a concept that combines vacation with learning how to sail. It is an excellent combination if you are just like me, and you like to learn stuff on your holidays, but you want also want to have a beautiful experience exploring the country.

Many times these chartering companies will offer ASA or US Sailing certified courses under an intensive course schedule. This means that you will have to do a lot of studying if you also want to get certified.

If you are less interested in getting certified and just want to acquire some new experience and learn some new tricks, you can also ask for that.

If you opt for one of the more open schedules (that are not connected to a certification), make sure you team up with like-minded people that want the same thing out of the course as you do. Otherwise, you might end up with another experience than you asked for.

A negative aspect of cruise and learn is that you will also have to share teachers between the students. This means less time for you than if you would get a one-on-one session. but the upside is that you will get To learn from the other students on your boat, and it will take off some pressure that often arises during a private lesson

The best part of a cruise and learn experience is that you will spend time with people who are in the same skill level as you and with the same interest as you, this is a good foundation for future friendship! 

Usually, setting up a likeminded crew is something that the charter companies will incorporate into the signup process, but make sure they really understand your intentions so that you and your friends get the most out of it 

Cost: USD 2195, 1-week cruise n learn

2. Online Courses

I think that online courses are one of the best ways to acquire a new skill,  Online courses show their true value in situations where you have many names or rules you need to remember.

For example, let’s say you want to learn all the different parts of a boat; there is no real use in getting a teacher to read the names aloud. Sure, you might pronounce some of the names wrong, but that doesn’t really matter.

But online, you will have the possibility to repeat what you need to repeat and move on when you have learned enough. This makes the online courses system very efficient.

Some might consider this system a little impersonal since you won’t have an actual classroom full of people to interact with, but most of this will be fully compensated by the fact that it is so effective.

The difference between online courses and reading books is that an excellent online course is very interactive; this means that it is based on “gaming theory,” a method created to make people use apps or games longer. 

This might seem weird, but when it comes to sticking around on an app or webpage because you need to learn the content, it is useful.

I would argue that online courses are perfect for learning rules and necessary names. But it is not able to teach how the boat will feel and handle on the water; for this, you need actual feedback from your ship and input from another captain.

On water training will teach you to understand when the boat is overpowered and, therefore, when it is time to put in a reef or how close to the wind you can sail in that particular boat. 


3. Learn From a Friend

Learning from a friend can be done in different ways, one way is to join a friend that is going out sailing, this will give you a lot of useful experience on the actual management of the boat, everything from docking to putting up sails.

If your friend is also a teacher or instructor in another subject, then this is a gold mine. Just make sure you reflect on what your friend teaches you so that you can use that information in the best possible way, you want to be using your head to understand what you just saw and not only repeat the same movements that your friend did!

Another way is to immerse yourself in sailing language, join your friend for dinner with other sailors, invite someone over to your house for drinks, and have conversations about sailing.

Most people enjoy sharing knowledge on a subject they love, and with sailing, it’s usually a hate or love kind of activity where people do it for their entire life or quit shortly after starting.

Make sure you offer something back, you don’t want your friend to feel that you are using him or her to save a few dollars, repay their help in a way you think suitable, help out on the boat, pay for snacks onboard, or something like that.

4. Teach Yourself

I have learned most skills on my own, that just my personality, I love going out and trying stuff and I have developed a good sense of what is a reasonable risk to take, and what is not.

If you know that you lack risk assessment skills, then this method is probably not perfect for you. If your risk assessment is solid, this method is very fulfilling and creates profound knowledge since it is based on your understanding of how you learn the best.

There are plenty of books to read, thousands of different types of great content written by people who have traveled the world many times. (check out my recommended gear page and see if you find something interesting).

If you don’t have the possibility of going out sailing on your own or with a friend, just find a sailor working on her boat and ask if you can come aboard and ask some questions.

Once you crack up a conversation and show interest in their hobby, the sailing community is usually amicable.

If you want free content that will make you a better sailor, sign up for my mailing list.

5. Join a Crew and Exchange Your Skills for Sailing Lessons

Joining a crew can be done in different ways, and there are many kinds of cruises that you can join. First, let’s look at how you can find a boat to join.

Online; There are websites such as FindaCrew or Crewseeker where yacht owners that are looking for the crew can post their needs and where wannabe crews can find a boat suitable for their wants.

On Crewseeker.net, it is free to look around, but once you have decided to contact a crew, you will have to pay a fee for the contact details. On FindaCrew.net, there are no fees for using their service.

Offline; One of the more adventurous ways is to hang around at marina bars, chit-chat your way to some useful information, sailing in the Caribbean and USA. This was a common way for people to find a crew.

It instantly builds a connection, and you can go out and have a sea trial with the captain to make sure you are a good fit for each other.

Suppose you feel that you don’t have the necessary skills yet to be a crew, don’t worry. Many skills are needed on a boat; you can market the skills you have.

Think outside the box, maybe you are good at creating an online presence and can help out with their web page or Instagram, or you could sow a new pair of cushions for the sofa, and in exchange, you will be taught how to sail.

There are so many different types of crews that you can join, yacht racing, yacht deliveries, and many more. I think you should check out the websites mentioned above if you are looking for any of the following;

  • Join an offshore cruise across the Atlantic
  • Sail in a specific part of the world
  • Want to learn sailing while also meeting new people
  • Get an intro to living and working aboard a boat.

6.  Playing Sailing Games or Simulators

Playing games when trying to learn the noble art of sailing might seem ridiculous to you old-school people out there, but I think it is genius.

Learning and having fun at the same time makes for such an easy way to absorb new skills, there is a time and place for tedious and hard work, but if you can make it fun, why not?

Sailing games, just like any other online or onshore activity, won’t make you into an avid sailor. But it will give you all the theoretical tools that you need. The games are similar to online courses but are way more interactive, and the skills are taught subconsciously by visual and emotional inputs.

I have identified three sailing games that I think you should have a look at;

  • ASA Sailing Challenge: USD 4
  • eSail: USD 25
  • Sailaway: USD 45

7. Old-School Sailing Lessons

In the US, there are two main actors on the sailing lesson market, ASA and US Sailing. Both offer curriculum to get you certified and improve your sailing. If you want to understand the differences between these two systems, you can check out my article on choosing the right sailing course.

Read my article on ASAS VS US SAILING if you want to know which is best suited for your needs.

In this article, I want to step away from talking about different schools and instead discuss more on types of different settings you can improve your sailing.

If you have a chunk of time, let’s say a vacation, then an all-out intensive course could be perfect. This type of training will be very hands-on and very high-paced, it usually requires nothing of you before you show up, but demands much of you once you join the class.

Often time the courses stretch from 1-2 weeks and align with some kind of certification. 

Intensive courses are great at building a foundation of knowledge, but make sure you plan to maintain your newfound skills by practicing once the course is over.

Like many other things, which can be achieved in a short time will also be lost in a short time, which is achieved over a long time, takes a long time to lose.


8. Charter a Boat

An enjoyable way to learn that is more relaxed than most formal educations is to rent a boat with a captain and then learn everything you can while sailing around some pretty islands.

It is similar to the “cruise and learn” concept, but here the difference is that there are no curriculum or fixed classes. This means that you will not get certified, and you might have to deal with less of an instructor compared to regular sailing schools.

The simplicity is the beautiful part of this concept, you only do whatever it is that you want to do, the curriculum is all yours, and you can ask whatever questions and practice whatever maneuver you like.

And when you get sick of it, you switch over to vacation mode, and the captain takes you where you want to go.

I use this way of learning almost every time I try something new, I ask a lot of questions, and when I feel comfortable, I suggest that I take a more engaging part in the activity.

If you are hiring a mountain guide, let them teach you how they set up their anchors, or if your snorkeling, ask them how they find the best spots for snorkeling.
You will be surprised how much knowledge is out there and how willing people are to share that knowledge with you.

USD2800 to 6160 for a week in the Bahamas on a Dufur 412

9. Go Racing

Competition makes people better, it pushes your skills to the next level, and you have people of the same caliber all around you.

Racing is not the best way to enter any sport at first, but once you get an ok understanding of the basics, competition and racing will supercharge your learning curve. 

The adrenaline and laughs will also connect emotions and cognitive functions, making for powerful emotional memories that are hard to forget.

Since racing is done under safe circumstances with the ability to get help in a few minutes, it creates a very safe environment to try new stuff and see where your limits are.

So when you end up in your first storm, you will already be able to handle the pressure, and this time your life might depend on it.

Racing only has one focus, how to reach the finish line the fastest, this one-goal mission simplifies sailing, and everything that is not directly leading towards faster track speeds will have to be moved down the prioritization ladder.

This leads to a strong focus on what actually works rather than just adopting “how things should be” or “we have always done it this way” types of mentalities.

Joining a race team will make your development structured, on your training days, every session will focus on one skill set that you need to improve upon. 

You will also be included in a community of like-minded, which is a great way to find energy and motivation to keep going when it gets hard.

If your ultimate goal is to sail around the world, then racing is not a perfect match; there are many differences between racing and cruising.

Cruising puts a big emphasis on comfort and safety; racing is all about speed and pushing the limits.

Even so, I believe that there are many lessons to be taught from racing that apply to cruising.

Joining a racing team doesn’t mean you are an all-out racer wanting to beat world records, it only means you enjoy a little bit of competition and are interested in advancing your skills as a sailor.

10. Become a Sailing Instructor

One of many things I learned from the armed forces was that if you want to make someone an expert, first make them an instructor. This might sound counterintuitive, wouldn’t you be an expert and then get to be an instructor or teacher? I would argue the opposite, here’s why! 

Becoming an expert in a subject takes a long time and a lot of energy, if you wait for someone to become an expert before you make them an instructor, you might never have any excellent instructors.

When will they have the time to acquire all those skills? Not only does the instructor need to know how to sail, he or she also must understand how the student is best taught.

I would argue that all you need is someone with the right character, a genuine commitment, and a strong will to learn. Once you put yourself on the track to becoming an instructor, your dedication and attention to detail will tenfold, this, I believe, is due to the want of being perceived as a kind and informed teacher.

Not only will you have to answer your own questions, but you will also have to prepare for all the questions that your students may ask.

You will also need a deeper understanding of the subject under discussion so that you can explain it through different perspectives and being able to make all of your students understand. All of this adds significantly to your skill as a sailor.

So if you have the basics skills figured out and you are serious about learning all you can, becoming a teacher or instructor is the way to go! 

But don’t worry if you don’t really feel up for a total commitment yet, you can also volunteer as a teacher’s helper, prepare lessons, rig the boats, and answer questions that you know the answers to. And when you don’t know the answer, you refer up to the main teacher, making you and the student learn something new today.

Cost: Read More

Learning How to Sail, the BEST Way! 

I believe the best way to become a proficient sailor is to combine all the different resources and methods mentioned above. Use the advantages of each approach to fit your personal needs. Here’s how I would learn how to sail if I had to do it again.

Firstly I would start off doing the free online courses, this will show me my blind spots, and I can get started right away. This first stage I call immersion is where I consume every little piece of information that I can get ahold of, playing games, watching youtube, talking to sailors, etc. Once I’ve got a little bit of the basics down, I’m moving over to the fun stuff.

Find a boat and a crew for on-water activities. I would get a small and easy-to-handle boat, and on sunny days with moderate winds, we will go out and practice sailing. If we could find someone with experience to join us, perfect, if not, it doesn’t matter; we will go out on our own (remember the risk assessment mentioned above).

After a few sailing trips, it is time to step it up a bit with paid online courses and one on one sessions

Now I know sufficiently enough about sailing that I am able to ask my teacher some good questions and to really challenge his or her skill set, I have identified, to some extent, what I don’t know and want to fill those gaps.

This part of the training will continue until I feel confident enough to join a cruise and learn or some similar experience.

Finding and joining a crew is perfect when I want to explore how the teamwork on a boat should work and how to handle a bigger boat, maybe I will charter a ship with a captain, or perhaps I’ll join a crew crossing the Atlantic.

After this step, it’s all up to your specific needs, have you identified more gaps in your knowledge and want to focus on them? Do you want to test your skills and go racing? Or maybe you’re ready to sail around the world! 

Whatever it is, go after it, and go after it HARD! Good luck 🙂

Learning How to Sail, the FAST Way!

If speed is the most important aspect then I believe these two steps are the most efficient way to meet your goals.

  1. Online courses
  2. One week intensive course

Total cost: ~USD 1500

Learning How to Sail, the CHEAP Way! 

This is basically the same way we did when we set out for the Caribbean.

  1. Free Online Courses
  2. Offer your skills in exchange for on-water training
  3. Play Sailing Games
  4. Borrow sailing books from your library
  5. Find and join a crew

Total cost: Free

How Hard is it to Learn How to Sail?

Learning how to sail is easy, once you have understood the basic principles of how a sailboat works, getting the sails up, and navigating to your destination is as simple as tying your shoelaces. Even though learning the basics is easy, becoming a great sailor is not and will take several years! 

How long does it take to become a good sailor?

Learning to sail can take anywhere from a couple of days, if you want to sail small boats close to shore, up to several years if wanting to acquire the necessary skills to sail around the world.


Owner of CatamaranFreedom.com. A minimalist that has lived in a caravan in Sweden, 35ft Monohull in the Bahamas, and right now in his self-built Van. He just started the next adventure, to circumnavigate the world on a Catamaran!

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