First, there are more moving parts on these boats. That means more things to keep an eye on and—this may sound trivial but it is not—more arcane words to learn. You’ll need to know your keel vs. centerboard, tiller vs. wheel, jib vs. Genoa, and topping lift vs. shroud.
Second, while all these boats can be sailed single handed, it’s more common to bring crew on board a larger boat. This means that you’re the captain and you are responsible for both keeping others safe and telling them what to do. Unlike learning on a small dinghy, you don’t have the luxury of making mistakes in private.
Third, bigger boats are heavier, go faster, and have more momentum. You have to anticipate the weather as well as your own movements and those of others further in advance, so that you can react accordingly and in time.
So how long does it take to learn to sail a bigger boat? How long to feel comfortable taking your own boat out as captain, either alone or with a few friends and refreshing drinks along for the ride? The short answer is anywhere from a week to a season of sailing. The long answer depends on these variables: sailing experience, geography, exit/reentry complexity, and learning style.
If you’ve learned how to sail a dinghy before—even if that was 30 years ago when you were 8 years old, bombing around on a tiny Optimist dinghy in a little lake—you will pick up bigger boat sailing quickly. While it might seem intimidating, once you recognize that the physics are exactly the same, you’ll have a feel for the wind direction, its effect on the boat, and what will happen to the boat if you turn to port or starboard. If you’ve never sailed before, it may take a week or two of both theory and practice to get used to the physics of sailing. The most important thing is to get to the point where you instinctively know whether turning in one direction or another will lead to the boat tacking or jibing. Tacking is a controlled shift of the sail and the boom from one side to the other, and a jibing is a more aggressive shift. Jibing is a more advanced maneuver and can be dangerous, so most beginning sailors stick to tacking when they need to change course. Getting a good instinctive feel for the dynamics between the wind, the sail, and the boat is what matters most.
Some places are easy to sail, some are extremely difficult. Weather, wind patterns, tides, and currents all play a role. Sailing clubs are sometimes tucked away in a bay or located in a spot where the conditions are calmer than a spot just a few hundred yards away. Geography can make it easy to learn how to sail, or really hard. If you live in a place with notorious tidal currents and heavy traffic like the San Francisco Bay, you will need to time your arrivals and departures carefully and understand where you should not go if your boat cannot beat the current. You’ll also need to be more scrupulous about learning right-of-way rules, how to maneuver away from other boats, and how to avoid container ships. If, however, you’re learning to sail on a small inland lake or in a calm bay with a steady wind that consistently comes from one direction, your biggest issue may be having to paddle your way back if the wind dies down. You can be a little more relaxed about not knowing everything before you head out. If your sailing environment is complicated, it will take a few more weeks or months to learn how to sail. You can shorten that time by learning from other sailors who know the local geography before setting off on your own. If it’s an easy sailing environment and you’re comfortable just getting out there, you can probably get away with some trial and error learning.
Some sailors say there’s no better entertainment than sitting in a marina bar and watching the boats coming in and going out, because you never know when someone is going to do something stupid. Thing is, while marina watching is fun and there are plenty of “oops” moments, there aren’t as many boats bumping into one another as you’d think. Just lots of close calls. Yet the configuration of the harbor, marina, mooring field, beach, or ramp where you’ll be landing or tying your boat is important. The most stressful moments of a day sail are usually getting in and getting out. If you have a Hobie 16 and you’re landing it on a beach with breaking waves, it may take half a dozen times to learn how to do that right. If you have a keelboat without a motor and have to sail it onto a slip in a marina, that’s tricky—it may take a week or two of dedicated practice to start getting comfortable with it. The important thing to note here is that if your marina is complicated or you haven’t been around boats much, expect to dedicate a little more time to feel confident in your maneuvers.
Your personal learning style may be the biggest factor in how long it takes to learn how to sail. If you learn by reading, you might spend a few weeks reading books about sailing before you even start. Maybe you’re a social learner and you like to learn by watching others. In this case you’ll probably find a way to learn by spending time on other people’s boats, which could take a while (depending on how much access you have to other people’s boats). If you’re a learn-by-doing type of person, you could probably buy a boat today and just figure it out as you go along. You may make some mistakes along the way, but so does everyone. If you like being taught by an instructor, or want to dive in and learn as much as possible right away, taking a course with one of the accredited sailing organizations will get you up to speed quickly. The American Sailing Association and the Royal Yachting Association both have excellent courses that lead to skipper certifications recognized by charter companies all over the world.
Learning how to sail doesn’t take that much time if your goal is to just get out there and have fun. It’s a great challenge that’s both intellectual and physical, and anyone who is determined can get going pretty quickly. Learning how to sail so that you can win races, survive extreme weather, and sail around the world, however, takes a little more time. Experienced sailors will tell you that they are always learning—there is always more to know about boats, navigation, the ocean, and the weather. Getting started in sailing is the easy part—it's stopping that’s hard!