However you get the itch to learn how to sail, there are some common pathways to learning the art of sailing. We talked in our post “Should I Take a Sailing Class” about the different courses typically available, and that is certainly a good place to start if you can work it out, but sometimes those courses are either far away, or they are offered on a schedule that just doesn’t work for you.
So how else can you learn? Well, assuming you are in an area with a Yacht Club or some other community sailing organization, take a look at their schedule and see what events they have, and not just the sailing events. Most clubs have a “social member” level. Consider joining so you can start meeting people and then listen for when they say “Jim can’t crew this weekend so we’re a person short.”
Certainly there are plenty of books out there you can read as well. And YouTube is full of sailing related videos. If you are luck enough to have a place to rent a small sailboat in a protected body of water, maybe all it will take for you to get the basics is to read up, watch a few videos, and go practice! Just know how much it will cost if you have trouble getting back upwind and they have to come get you with a towboat.
Racing with other crew can be intimidating, but racing is a great way to learn to sail. The entire race is usually predicated on sailing at both points of sail upwind and downwind and to do it in an optimal way. So, in theory, you get to learn the best techniques for all points of sail as you learn different positions in the boat.
At the end of the day, the best way to learn is to Sail MORE!