You’ve watched the beautiful sailboats gracing the bay as the sun sets, you’ve read articles about how much fun sailing is, maybe you’ve been out with a friend or paid for a sunset cruise. You’ve decided to go for it.  You’re going to learn to sail!
So…  Now what?  How do you learn to sail, anyways?
There are basically three models you can follow:
- Jump in a boat and fiddle with things until you figure it our (the “independent†model)
- Read a few books, watch some youtube videos and get practice by crewing for somebody else who knows what they’re doing (the “self-taught with mentor†model)
- Pay for professional lessons and get a certification (the “professional instructor†model)
Learning to Sail the Independent Way
There are certainly examples of people who’ve just figured things out on their own, maybe with the help of some youtube videos.  Sailing isn’t actually that hard once you get the feel for it, so it is possible to do it this way.
However, there are a few finer points that are easy to show and hard to explain.  If you haven’t sailed on a well-sailed boat and gotten a feel for it in the seat of your pants, you can drag yourself all over the bay thinking you’re doing fine when a moderately experienced sailor would think you’re poorly trimmed or wildly out of control.
Most importantly, though, you can miss basic safety lessons like crew overboard and reefing unless you’re working from a syllabus of some kind, and poorly executed maneuvers can be quite dangerous, especially in larger boats.
Just messing about can be dangerous. Â It can work for some, but I highly recommend against it.
Learning to Sail by Self-Teaching and Mentorship
If you’re on a budget, it is definitely possible to learn by reading books and watching videos and then getting some real experience with somebody who knows what they’re doing.
This will take more time than formal lessons, and you’re likely to pick up some bad habits, but it can be done safely as long as you
- work from a syllabus so you don’t miss any important concepts, and
- find a mentor who is knowledgeable, safe, and patient.
The second point is a lot harder than the first!
Finding a Syllabus
There are many books available if you’re a “book learner.† This learning style works for me, and I used The Annapolis Book of Seamanship when I was learning.  I highly recommend it.  It takes you right from the very basics through all you need to know to safely skipper a boat.
Even if book learning isn’t really your style, you could get a book and then at least use it as a reference so that you can make sure that you’re learning the right things.  You can then supplement with youtube videos or lessons from your mentor.
Another great option is to learn through an online course.  NauticEd has a full syllabus of courses from total novice to offshore sailor.  They’re interactive, high quality, and associated with the British Royal Yachting Association which is the most respected sail training institution in the world.  You can (and should) take the Basic Sail Trim and Navigation Rules courses for free to see if you like them.
[I do receive a small commission (thank you) at no cost to you if you click the NauticEd link from this site and end up deciding to pay for some courses.  I wouldn’t recommend them if I didn’t think they did a great job.  I wish they were around when I was learning.]
Finding a Mentor
Now that you have some theory under your belt and you know all the things you need to learn to be safe on the water, it’s time to find a mentor…
This can be tricky for two reasons
- Most people don’t know any sailors
- There are a lot of sailors who either don’t know as much as they should or just aren’t very good teachers.
So, if you’re lucky enough to know a competent, patient sailor then you’re away to the races.  If not, you’ll either need to get creative or pay a professional instructor.
OK, like many people you probably don’t have a sailing friend to call on.  Or maybe your only sailing friend is still inexperienced or even a bit of a yeller.  What to do?  In order of increasing likelihood of success:
- Try walking the docks.  In many places, there are marinas with open gates where you can just go down and walk around looking at boats.  Sailors are a friendly bunch and they usually love to answer questions.  They’re usually working on some maintenance task and would also love the excuse to stop and talk about the thing they like the most: sailing.It takes some courage, but it you time it right, you might find somebody on the way out for a quick sail who would like some company.  If you hit it off on the sail, you might have just found a mentor.
- Post on an online forum such as Cruiser’s Forum or even your local craigslist or meetup.com.  Describe where you are, what experience you have and what your availability is.  There are often sailors who are looking for crew.  It will help if you offer to bring the beer and sandwiches or help with maintenance.
- Try walking around a boatyard. Â This is where boats are hauled out for maintenance. Â Skippers often do their own work and it sucks.Two weeks ago, I did two back to back 11 hour days scraping, sanding, painting and waxing in the sun. Â If somebody had walked up to me and offered to help in return for a few hours sailing, I would have jumped at the opportunity.
- Find a racing crew.  This one surprises people.  Most places have weekend or Wednesday night “beer can†racing.  It’s just normal folks in normal boats doing some racing after work.  The skipper has a boat and a desire to win, but can’t even get to the starting line without 3-8 willing crew.  It’s free to crew and crew are always in demand.If you show up looking keen, you are virtually guaranteed to go sailing.  Most clubs that I know have a “no crew left behind†policy and will find a boat for you.  It helps if you bring a life jacket, non-marking shoes and a six-pack of beer.
I cannot emphasize enough that most (but not all) people really need to find somebody who is a good fit for them personally.  Frankly, some sailors become yellers when things aren’t going quite right and most people don’t learn well when being yelled at.
Be especially wary of “fit†with your mentor (or professional instructor) if you’re a couple and one of you is more into the idea than the other.  A die hard, enthusiastic beginner might put up with an impatient mentor, but somebody who’s already feeling trepidation will shut right down, potentially scuppering the plans of the enthusiast.
Learning to Sail with a Professional Instructor
I highly recommend this path in the very beginning.  Once you’ve laid some groundwork, you can shift into the self teaching and mentorship model if you wish, but some professional instruction will get you started right.
Most sailing towns will have plenty of options for sailing instructors. Â Look for an instructor who you really click with. Â Everybody has different learning styles, and good instructor/student fit can make a big difference.
Some women will prefer a women only class. Â Many women learn differently than men and this removes some of the social pressures as well. Â Women only classes are available in many cities.
Classes can be in the evenings or weekends, but I really like the 3-5 day live-aboard format.  You are totally immersed for days on end, so you get a chance to really get the feel for things and you’ll usually be anchoring out somewhere so you can learn some overnight cruising skills as well (you can even choose to do this format in a destination such as the Caribbean for full effect!).
A Hybrid Model
The reality is that most people will mix and match the above models a bit to suit their needs. Â This is exactly what I did.
I took a weekend course, sailed with some friends, bought my own boat and some books and self-taught for a while, joined a racing crew, and then used a professional instructor on three different live-aboard courses to get my Offshore Skipper certification.
I do think that even if you decide to go with professional instruction, you should consider doing some self-guided learning before the course.
There’s a lot of theory at the beginning and it can get in the way of just sailing the boat.  If you’ve invested some time beforehand with a book or online training, you’ll get much more out of your time on the water.
What Size Boat?
It’s worth a note on what boat size to learn on.  Small is beautiful in this case.  Smaller boats are much more responsive and you’ll get much faster feedback from the boat.  You’ll be able to feel whether you’re doing the right things much more easily, so you’ll learn faster.
Smaller boats aren’t always practical, especially if you’re going to be living aboard during a week-long course, but a great way to start is with a local dinghy sailing club.  When you make a mistake, you’ll get wet, so it’s not for everyone, but you’ll learn quickly!