Opening up the workbook for the U.S. Sailing basic keelboat certification is sort of like opening up a Chinese elementary school textbook for the first time.

Sure, some of the initial chapters focus on rote memorization (parts of the boat, points of sail, safety precautions). But other diagrams — wind flowing over sails, the direction the telltales flutter — stared at me angrily from the pages, daring me to decipher what they meant.

Learning to steer a sailboat

Marketing coordinator Kensey Wheeler takes the tiller while instructor Kelsey Guy kicks back. It was amazing how relaxed the Sail Nauticus team was while giving us control of the boats — much calmer than my mom when I was learning to drive her car.

“Sailors have their own language,” is what our instructor Ryan would tell us on the first day of class. “It’s almost exclusive.”

But it’s not the seemingly foreign tongue that makes sailing so challenging for a newbie. In fact, the vocabulary isn’t that difficult to pick up as part of a fast-paced, weekend certification program.

It’s the practical, hands-on skill set that stumped me. I would later learn that even seasoned sailors spend the rest of their lives perfecting all the details. Sail trim, anyone?

Attach the main halyard

Hoist the mainsail! If this pregnant lady can learn how to sail, so can you.

Day 1: Multitasking

After my first day, it struck me that multitaskers are probably excellent sailors, at least on small boats like the Harbor 20s we were sailing. Even on relatively calm Chesapeake Bay waters, our team was faced with an ever-changing wind, which meant that what was correct ten seconds ago was no longer accurate.

It also meant my brain was in a constant state of processing, like a pinball being flipped around a pinball machine. “What’s my point of sail? Do I need to tack or jibe? Who has the right of way here? What the h*&! is that other boat doing?!? Should the mainsheet be trimmed right now?” And if you’re not (frequently) asking yourself those questions, the instructor will ask them of you. Commence system overload.

And just when you’ve sorted out the answers, one of your crewmates will accidentally fall onto the mainsheet block when the boat heels over and lacerate her neck with the mainsheet, leaving a rope burn resembling the BVIs on her neck.


Elizabeth River, here we come. DMM email guru Nikki Tallmadge takes the tiller, while Marketing Coordinator Kensey Wheeler prepares to leave the dock.

Day 2: Man Overboard

Day 2 of our training brought more classroom time, more sailing time, and more familiarity with the boats. Even routine things like figuring out what you need to release/tie down/uncover to get the boat away from the dock can take some time to master for new sailors.

“Man overboard” drills were the theme, with two newbies per boat (plus the instructor) taking turns at the helm to rescue “Bob,” the buoy. (It is worth noting here that at 8 ½ months pregnant, the only action I couldn’t perform the entire weekend was folding myself over the side of the boat to pull up Bob. So if you fall overboard, don’t count on any pregnant ladies to rescue you. They will instead be sipping a virgin cocktail, watching while you flail, and waiting for someone else to save your sorry behind.)

We also learned that falling overboard is the last thing you want to do, as the rescue process involves hitting you with the vessel (first with the bow, and then with the stern) before dragging you back up into the boat. And then laughing at you. Fortunately, the stability of the Harbor 20s makes a man overboard unlikely.

Day 3: Accidents Happen

Day Three started out with a thump as crewmate Kelly and I watched another newbie run into the pier on the way out. No injuries to the boat or crew, but it reminded us how easily accidents can happen, even with an experienced instructor on board.

The Wrap: Certification Test

Throughout the weekend, we newbies had expressed concern about the certification test at the end. How hard was it? How much did we need to study? We were assured that, as intelligent individuals, we would have no problems passing.

What a lie that was.

The 80 question test definitely made sure we’d really absorbed everything, and all of us felt we could have benefitted by studying a little more. In fact, one person in our group had to take it twice. U.S. Sailing definitely does not hand out certificates to anyone who pays for the program.

On the other hand, even while I proudly stand here with my shiny new U.S. sailing log book in hand (the trophy from successfully passing the class), I feel a little overwhelmed at how little I know about sailing. With people like me on the water, aren’t we all in danger?

But I suppose the point of the course isn’t to produce experienced sailors. It’s to equip us newbies with enough know-how to get out on the water and start practicing — where the real learning starts.


DMM Sailing graduates (center, L to R) Kensey Wheeler, Nikki Tallmadge, Lauren de Vlaming and Kelly Meyer are flanked by Sail Nauticus instructors Kelsey Guy and Ryan Newland. No booms to the head this weekend!

So if I ever find you flailing about on the Chesapeake, I am now certified to hit you (er, rescue you) with my sailboat. And in a few weeks, once I get rid of this large belly, I’ll even be able to pull you out of the water.

For more information or to find a course near you, visit the USSailing Learn to Sail page.