So You Want to Learn to Sail? Two Essential Questions to Answer Up Front


While flipping through the Sumer 2013 issue of Outlook By The Bay, I came across a wonderful article that will help anyone considering going to sailing school make the decision about which school is right for them.  While we believe that J World Annapolis is the right school for anyone looking to learn how to sail, improve their sailing skills, obtain US Sailing certifications or hone their racing skills; we think the following process is a good one for every would-be sailing student to consider.  Re-printed with permission from Outlook By The Bay.

So You Want to Learn to Sail?
Two Essential Questions to Answer Up Front

By Henry S. Parker

            So this is the year, you’ve told yourself you’re going to learn how to sail, or take your sailing skills to the next level. How better to enjoy the beauty of the Bay, to intimately experience its wonders, mysteries and challenges than with a confident demeanor in the peaceful cockpit of a swift, sleek sailing craft, with the water’s surface so close that you could touch it.

            But before you embark on this worthy goal, you would be well advised to first answer two essential questions: Why do you want to do this? And where will you learn the skills? Let’s tackle these in order.

Why do you want to do this?


A tougher question than you might think, with many possible answers. Maybe you’ve always dreamed about learning the skill, but never had the time, wherewithal or confidence to pursue it. Perhaps you already sail on friends’ boats, but want to feel more like a participant than ballast. It could be that you’d like to crew in sailboat races. Possibly you aim to own and operate your own boat. Alternatively, you plan to charter a boat from time to time. Or maybe it’s a bucket-list sort of thing, like sky-diving or bungee-jumping. Learn the skills, do it once or twice, then check it off the list and move on to the next challenge.

Whatever your motive, it’s important to identify it up front. Then ask yourself some probing questions, answer them honestly and face some hard truths. For example:


  • Do you really know what you’re getting into, especially if you plan to skipper a boat? Are you prepared to deal with the possibility of bad weather and gear breakdowns and the inevitable rocks and shoals—literal and figurative—over the bounding main? Will sailing be a (willing) family activity? If not, are you prepared to spend long hours away from significant others? Are they supportive of such separations? Know that the sport of yachting teems with sailing widows and widowers.
  • If your intent is to charter, are you sure you want to spend limited free time and funds on an unknown boat with a misty history? After all, you could be lounging poolside in a luxury resort.
  • If you plan to own and operate your own boat, can you afford it? Not just the boat itself, but unending repairs and maintenance, equipment (including that which is safety-related), sails, launching, mooring, hauling and Winter storage charges, BoatUS towing fees and the costs of an underwater salvage operation (just kidding). Remember the old adage, “A boat is a hole in the water into which you pour money.” And be acutely aware of the “gonna need a bigger boat” syndrome.
  • Even with the best instruction in the world, all sailors learn best by doing. Are you prepared to learn from—and accept the consequences of—your inevitable misadventures and mistakes? Think running aground in distant waters with bad weather closing in and a crew who wants to go home now.


Where will you learn the skills?


There is no better place to learn to sail than on Chesapeake Bay. The environment is beautiful and the waters are usually gentle. Instructors and programs are top-notch. And the area is steeped in sailing tradition. But specific answers to the question, “Where will you learn the skills?” depend on the response to the previous question. If your goal is to better enjoy sailing on friends’ boats, you could learn a lot by watching, asking questions pitching in, —and save the cost of formal instruction. To some extent the same is true if your aim is to crew in races. You can also take in free seminars offered in waterfront towns like Annapolis. But if you plan to skipper a boat, or upgrade your captain skills, it’s best to take a course.

A quick online search will turn up a host of instructional programs, including several on Chesapeake Bay. Some are offered by specialized (often national) sailing schools, others by yacht clubs or community sailing organizations. Most have a track record of success in producing trained, satisfied and confident graduates. But there are significant differences among programs. You’ll want to choose the best fit for you. How to do that? First, make sure that the school is accredited, that the instructors are certified and that graduates receive certification by a recognized organization such as the American Sailing Association or US Sailing. This will help confirm that the program is adequately insured and that it has a successful record of safety and success. It will also facilitate sailboat chartering after course completion.

Additional considerations are largely a matter of personal goals and preferences. These include:


  • Type of course  Many schools offer both a small-boat and a keel-boat class, and some schools offer advanced courses—even instruction in racing. Your choice will depend on the size of the boat you intend to sail, your prior experience and your sailing goals. Beginners may find it easier to learn the fundamentals in a small boat, even if they intend to sail a keel boat.
  • Class duration  Most schools assert that they can teach the fundamentals of sailing in three to five days. Longer courses provide more time for interaction with instructors, unstructured learning, practice and building confidence. They may also cover specialized topics like sail handling, engine maintenance, navigation, heavy weather sailing and reading winds and currents. Longer courses provide some insurance against the loss of on-water time because of inclement weather.
  • Time on the water  Some classroom instruction is necessary and may be dictated by weather, but hands-on time on a boat is the best way to learn.
  • Class size  Most classes are limited to three to five students. In general, and depending on the instructor-student ratio, the smaller the class the better, because students can get more personal attention and greater depth and breadth of course content. Longer courses can offset the disadvantage of larger classes.
  • Your classmates  It’s difficult, if not impossible, to know in advance who your fellow students will be and how they will behave at sea. Nothing chills the learning environment more than a distracted kid, a know-it-all novice, a panicky shipmate or an enrolled couple with land-based issues that spill over onto the water. Should this discourage you? Not necessarily. Good instructors will know how to effectively handle these situations and keep the course moving well. You could also consider signing up with friends or other members of the extended family. And there are some great courses for women only.
  • Cost  Short courses can cost $500 to $1,000. Longer courses, obviously, cost more.

Ready to start looking for a school? Consider the following approach: First, do a thorough online search. Here’s a good start: Second, talk to other sailors, especially those who have taken courses. Finally, visit as many sailing schools as you can, talk to the instructors, check out the boats and facilities, and ask questions. Then take the plunge! Chances are it will be one of the best decisions you’ll ever make.


Henry S. (“Hank”) Parker is an avid sailor on cruising and racing boats, a sometime boat owner, and a former sailing instructor. He grew up in a sailing family on the Maine coast where his father owned a boat yard and did not give his children the option not to sail.  He can be reached at


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