From my seat at the helm, it looked like our boat was coming in close enough to the dock, but our approach wasn’t pretty enough for my sailing instructor, a fastidious Belgian named Phil. On Phil’s cue, I tacked and we glided into the space behind the row of boats perfectly parallel to the dock with only a few inches to spare. Then, like Jehovah when he’s pleased, not when he’s pissed-off, a deep sonorous voice called out loudly from out of the heavens: “GOOD JOB! WAY TO GO!” punctuated by raucous cheers and applause. “Could that voice be talking to me?” I wondered, “Where’s it coming from? Who could it be?"

After we disembarked, Phil showed me how totie up and de-rig the boat; I tried my best to imitate his meticulousknot-tying techniques, but the distracting questions kept coming: “Was I havinga mystical experience? Or a psychotic break?” While bending over and rolling upthe mainsail, I saw 2 feet. “Oh no, it’s a visual hallucination now, “I thoughtas I looked up and saw that the feet were attached to legs, attached to abarrel-chested torso, attached to a round mustachioed face with a jolly grinstretching from ear to ear. I stood up, thinking: “If they’re going to take meaway in a straitjacket, I might as well go bravely like Joan of Arc. It can’t bethat bad…Maybe I won’t have to pay taxes….”

I was relieved when Santa Claus of the Sea startedtalking. Could he be a real person? “That was THE best docking job I’ve seen a studentdo on their 1st day all season!!” he said excitedly. (And that was saying a lotbecause it was the 3rd week of Sept. and the season had started inApril). “Hi, I’m John Cosby,” he said, smiling. As we shook hands, I introducedmyself, saying: “I only did what Phil told me to do.” “But YOU did it!!” hesaid exclaimed, the word “YOU” resonating in the air like a sonic boom. It musthave been the voice I heard! “That was you cheering when we docked, wasn’t it?”I asked. “Oh yeah, that was definitely me!” he said, laughing heartily beforeheading upstairs to his office.

Over the next 2 days, I practiced tacking,jibing, man overboard and figure 8 drills, reefing the mainsail, andheaving-to, as well as rigging, de-rigging, and docking the boat. I had adifferent instructor each day, and while they all demonstrated anextraordinarily high level of expertise, they had distinct personalities andindividualistic ways of doing things. My instructor on the 2nd day, Chris,was an intuitive, who trimmed the jib behind his back as he watched me steer.“How can you do that without looking?” “Oh, I can tell what’s happening fromthe sound it makes.” Incredible! My instructor on the 3rd day, IslandJohn, barely touched things and they moved in a big way. “Let the wind do thework for you,” he said calmly, like a hypnotist.

After enduring a 100-question written testthat did not include 1 single question about swearing (much to mydisappointment, because I have considerable expertise in the subject) and successfullytying a few knots, I had passed my Basic Keelboat Sailing (ASA 101) course atthe Annapolis Sailing School, and became a certified member of the AmericanSailing Association. And here I thought I was certifiably cuckoo-bird crazy onlyto find out I’m really just a sailor! 

It’s widely known that the Annapolis SailingSchool is the oldest commercial ASA sailing school for adults in the U.S.,founded by Franklin “Jerry“ Wood back in 1959, who 11 years later, co-foundedthe U.S. Sailboat Show with Bennett Crane.[1]But not everybodyknows the back story about the people behind the legend. Glitterchicken is hereto deliver the goods!

In 1961, Wood asked the renowned Olin Stephens[2] to design him a boat that would bring 3 drunks home safely in a storm.[3] Stephens sketched out the plans for an uncapsizable, indestructible 24’ sloop on a dinner napkin, which ultimately evolved into the blueprint for the  Rainbow boats the school uses to train its students to this day. This isn’t just nautical myth. “It’s a true story,” attests John Cosby, who currently serves as Managing Director and Head Instructor.

Cosby began working for Woods for a mere $18dollars a day as a junior instructor when he was 15 years old. A native ofnearby Severna Park, Cosby’s father had been a U.S. submarine commander whopurchased a sailboat after retiring from the Navy.  Faced with the futility of arguing with hisfather, Cosby spent countless hours on the Magothy river as “forced crew,” wherebyhe established sailing skills that surpassed instructors twice his age. Cosbyrose quickly through the ranks due to his impressive skill set and his workethic, becoming Marina Manager when he was only 21 years old.  In those days, General Manager Rick Franke wasin charge of classroom instruction at a facility in Eastport, while Cosby was responsiblefor on-water training operations at the school’s current Bembe Beach location.

Although Cosby stopped working at the school in1983 to pursue career goals that eventually took him out of the boatingbusiness for a spell, his connection to the Bembe beach property deepened furtherwhen he married girl-next-door Hilary Wilson in 1985. The Wilson family ownedthe property immediately adjacent to the school, where they had a rustic beachcottage they used as home base for summer sailing activities. Over the years, 5out of the 7 Wilson siblings worked as sailing instructors, which is ano-brainer when you consider the fact that kids were expected to earn their ownspending money back then and the Wilsons lived so close to the school they couldhave sleepwalked to the docks in the morning. Although it would have added adash of spice to this story, Cosby won’t admit to sharing any romantic momentson board the Rainbows with Hilary. The way he tells it, they started dating whenHilary was attending college. (Bland, we know, but Glitterchicken faithfully upholdsthe journalistic duty to tell the truth, no matter how yawn-inducing it may be).

DON’T STOP READING NOW! True, we can’t giveyou a titillating screenplay for a Rom-Com or Coming-of-Age flick,  but what happens next has all the hallmarks ofa great Drama: a series of cataclysmic events occurs, presenting our characterswith obstacles that would have been insurmountable had they not joined forces,and at great risk, taken a leap of faith into the abyss, hoping that theirinnovative solutions would not only save the sailing school from ruin, butbreathe new life into it, making it better than ever before! (This is calledforeshadowing).

The 1st event that shook the Annapolis SailingSchool’s foundation to its core was the death of founder Jerry Wood in 2003.His widow, Kathy, bravely carried on the business until her death in 2005,after which the estate sold the property, all the structures on it, and theentire fleet (which had grown to be quite substantial by that point, including12 cruising boats) to Tim Dowling, who, like John Cosby, had started as ajunior instructor when he was 15 years old and had worked his way up to GM.[4]

Unfortunately, Dowling’s plans to build upon Wood’s legacy and further his vision were cut short by the 2nd apocalyptic event, the Great Recession of 2008 and its painful aftermath that lingered well into 2012. Like all leisure industries, “the boating industry was practically decimated,” says Cosby.  For the thousands of Americans losing their jobs to layoffs and their homes to foreclosures, trying out a new sport wasn’t exactly at the top of their agenda along with food and shelter.  Confronted with rising costs and drastically reduced revenues, Dowling was forced to start selling off assets little by little in order to stay afloat (Pardon the pun).

Then, one fateful day in 2012, Cosby, who was staying at the 2nd incarnation of the Wilson family’s summer home next to the school, accepted receipt of a certified letter. He recalls the “visceral” reaction he had when he read the notice of Dowling’s intent to sell the Bembe Beach property to commercial marina developers. Not only would this spell death for the sailing school, but it would negatively impact the serene, woodsy residential neighborhood surrounding Bembe Beach road and turn it into a bustling thoroughfare, which would increase traffic congestion, speeding, pollution, and overall “obnoxiousness.”

The Wilsons held a brainstorming session to figureout if there was anything they could do to prevent catastrophe from happening. EnterRick Nelson, investment management executive from NYC married to Hilary’ssister Jenny, who had also been an instructor at the sailing school back in theday. A plan was hatched for Rick and Jenny to buy the property and thebusiness, including the fleet, which by this point had deteriorated to “maybe18 decrepit Rainbows and 2 Beneteau cruising boats,” according to Cosby, who wasto quit his job at West Marine to become Managing Director and Head Instructor.Faithfully executing their plan, the Nelsons officially became the new ownersof the Annapolis Sailing School in November of 2014, beginning a new chapter inthe school’s rich history.

I first met the Nelsons in 2018 at thebonfire party (complete with apple cider and s’mores) they hosted for KeelboatClub members during the Fall Sailboat Show weekend.  I felt instantly comfortable with Jenny. She struckme as an anti-princess, who wouldn’t hesitate to chip in and get her handsdirty doing whatever kind of work is necessary to fulfill a task, instead ofsitting back and complaining about the “help.”[5]  I found Rick to be extremely approachableand easy to relate to because he has a bit of the dreamer in him as do I. Withinminutes, we discovered we had a shared love of classic films and we were concoctinggrandiose visions of sailboat cruises for film buffs.

What Rick tells me is heartening.  He points out that the school’s “primary goal” is to encourage new sailors “to have a good time while being safe” and emphasizes that the school’s official tag line is “Seriously Fun,” distinguishing it from other sailing schools in the region that focus on competitive racing techniques. In this respect, he and Jenny are staying true to Wood’s original concept. On the other hand, Rick is cognizant of the fact that times have changed. Thus, the Nelsons have re-imagined the school to appeal to the “modern sailing family.”  Glitterchicken’s here to tell you how they did that.

First of all, the school expanded its fleet to better accommodate its children’s summer program called KidShip that was started back in the late 80s. Many of today’s parents want to engage their kids in healthy outdoor activities without the pressure and time commitment imposed by joining traveling sports teams. They’re delighted to see their kids “out there enjoying themselves out on the water, detached from their electronic devices,”[6] says Cosby, pointing out that there’s no other children’s summer sailing program in the region like KidShip. Sure, there are 2 private clubs offering children’s sailing camps, but they’re all about being “first to cross the finish line,” the antithesis of chillaxation.

Furthermore,the Nelsons have also made substantial improvements that enhance both the beautyand functionality of the beachfront property located at the tip of the peninsulaon the south side of Back Creek Inlet, which boasts spectacular views of theSevern River. With the assistance of dedicated staff, they totally repaintedand refurbished the main building, which is home to the administrative offices,restrooms, some of the classrooms, and the repair shed. Other enhancements include a sizeable tentedevent space that the school rents out to private parties for weddings and otherevents, and floating docks that are used not only by sailing school studentsbut are leased out to the Blue Lotus Yoga Studio for their unique on-water yogaclasses and festivities such as their Summer Solstice Bash.[7]

But myfavorite improvement attributable to the Nelsons is the conversion of the formersail storage shed into a glass-walled Club House with a sliding door openingout onto a darling little deck overlooking the boating activity on Back Creek  and the “Maritime Republic of Eastport”[8] beyond. I did not believe in love at first sight until I sawthe Club House. Now, like Davy Jones of the Monkees once said: “I’m aBeliever.”[9] Here’s where instructors and students hold graduationceremonies and Keelboat Club members gather to debrief over cold beers whilewatching the sun set after Monday night Rainbow regattas. Still dubbed the“Sail Shed” by instructors who have been working at the school since its barebonesdays, the Club House is tastefully appointed with nautical-themed décor and furnishedwith tables and chairs, sofas, a full-sized bar, Keurig coffee/tea maker, mini-fridge/freezer,an enormous TV, and musical entertainment provided by Alexsa. Although not ahuge space, with all these amenities you could safely say the Club House is swank.Or if you’re a Brit, you could say it’s downright posh.

It’s noteworthy that the Nelsonshave also made substantial investments to expand the school’s cruising fleet,which includes 2 Beneteaus (37’), a Catalina (30’), and a Newport (30’),whichare used for the ASA cruising courses and “Evening Sails,” where the generalpublic can charter a boat with a captain for a few hours; BYO beer or wine onboard and the school will provide the hors d'oeuvres. You can ask to steer orserve as crew or just lay around on deck like a diva while your fiancé showersyou with rose petals.[10]

And finally, although not aswell-publicized as their ASA course offerings, the Annapolis Sailing School offersprivate instruction (aka “PI”) for new boat owners. There are 6 captains forhire that will take you out on your own boat, give you docking practice, or helpfigure out some other “bugaboo that you need to get past,” Cosby says.

Although the first 2 years after the Nelsonstook over were “rough” as the school struggled to rebuild its fleet and secureits footing in the post-Recession economy, Cosby is pleased to report that theschool is experiencing its 3rd straight season of “fantastic”growth.  He maintains his guiding philosophythat if the school continues to focus its efforts on “being successful with ourstudents, the financial stuff will follow.” A humble man by nature, Cosbycredits his instructors and staff as “the key to the school’s success.”Although I agree wholeheartedly with this statement, I would add that Cosby deservesa good portion of the credit for the level of excellence demonstrated by hisemployees.  He makes 100% of the hiring decisionsand when asked what’s the most important quality he looks for in an instructor,he replies that while sailing skills are an important factor, they’ve got to be“people persons” first and foremost. Cosby explains: “I’d much rather take areally great teacher and teach him or her to sail instead of taking a greatsailor and teaching him or her how to teach.”  

From a student’s perspective, the valueplaced on extraordinary teaching ability at the Annapolis Sailing School is readilyapparent. Although they differ significantly in age, experience, personality,and technique, all the instructors I’ve encountered have one thing in common. Nomatter how dense you are, and how long it might take for your muscle memory to“get it,” they don’t treat you like an idiot or a screw-up, which would only demoralizeyou, thereby thwarting the school’s goal of getting you to enjoy sailing. Nordo they dwell on what you’re doing wrong, prompting you to ruminate on pastmistakes, which would only cause you to make more mistakes.

On the contrary, Cosby’s sailing instructors highlightthe things you’re doing right, which puts those things at the forefront of yourconscious mind, where you’re more likely to repeat them. By employing thiscoaching method, they keep you focused on the present, where you always need tobe whether you’re on the water or on land. In this way, the art of sailingbecomes a metaphor for life and if you bring a positive attitude into the boat,you just might acquire some wisdom and mental fortitude along with some cool knot-tyingskills you can bust out at cocktail parties. I can honestly say that the greatestgift I’ve received from Annapolis Sailing School instructors is that they havehelped me to believe in the concept of limitless possibilities, which used tosound like a cliché phrase, but now feels like an unwritten natural law I hadalways known but had somehow forgotten along the way.

In my estimation, the secret to the school’ssuccess is that Cosby embodies the qualities and demonstrates the behaviorsthat he wants his instructors to emulate, which is the very definition ofleadership. Cosby serves as the central role model for the hands-on, practicalcoaching method described above that is referred to as the “Annapolis Way”developed by Jerry Wood and his protégés, with the intention of luringrandom people in off the street and engendering in them a lifetime love ofsailing. Sounds ambitious, right? Yeah, well Cosby makes it look effortless. Hegleefully chuckles, bellows encouraging words, and beams with pride when hewitnesses his students’ accomplishments the same way a father glows withexcitement when his child takes his first steps or rides her bike without trainingwheels.[11] That’s why my nickname forCosby is  “Happy Pappy.” And the analogyis fitting. No matter the birthdate on our I.D. cards, all newbie sailors arebabies and the powerful effect of these paternal reactions cannot beunderestimated; they inspire in us an immediate sense of confidence and trustin our own capabilities. This means the world to a klutzy, uncoordinated girl likeme and was always one of the last kids picked to be on anybody’s team in gymclass and still walks into furniture stone-cold sober.

Another important factor contributing to theschool’s success under its new management is that Cosby doesn’t take forgranted the valuable contributions made by his remarkably capable staff membersincluding the Nelsons’ amiable son Ricky, artistic Brenda Reed, and liveaboardcruiser Kara Finneren, who do all the behind-the-scenes work required to keepthe place running. On top of that, I can attest to the fact that the staff areperennially welcoming and accepting of students and Keelboat Club members fromdiverse backgrounds and lifestyles and do their very best to answer ourquestions and accommodate our requests. They’re the kind of folks who give youfaith in the human race.

Despite his deep appreciation for his facultyand staff, Cosby says that the school’s greatest challenge (besides theweather, which nobody can control) is finding and retaining employees thatmeasure up to the school’s high standards of quality. Sailing instruction is apart-time seasonal occupation, and while the staff positions may have morefull-time potential, they can hardly be described as lucrative either. It’shard to pay the bills for people with mortgages, kids, and car payments, sothese jobs appeal mainly to college students and retirees, making turnover aconstant headache.

Nevertheless, due to the school’s highly regarded reputation and its proximity to the Washington, D.C. metropolitan area, Cosby still manages to attract stellar new talent, such as Dan Nichols, a former State Dept. employee who currently consults for non-profits. Nichols learned to sail on Lake Erie (Pt. Abino, Ontario) before honing his skills on the competitive racing circuit in Newport and Nantucket. This season, along with sailing instruction, Nichols began officiating Monday night Rainbow regattas for Keelboat Club members along with Jack-of-all-Trades Andrew Moe (you name it, he can fix it) and Buddha-of-the-Bay Art Holt (nothing short of nuclear war could harsh this dude's mellow) who have lent their own personal touches to overseeing the Rainbow regattas, maintaining the school's fleet, and caring for its students.

Nichols “agrees completely” with Cosby when he says that “it’s the people behind the school.” (He’s praised Moe, Holt, and other instructors and staff in previous conversations). But I can’t help thinking that Nichols is one of those edifying people who’s already making the school a better place. Not only does he add a touch of class to Cap’n Cosby’s crew, but he’s a devoted father who’s most likely drawing from a similar paternal emotional well when he says: “It’s such a joy to meet new students who are anxious to fulfill their dream.” When asked what he likes best about this gig, Nichols says: “Teaching here side by side with top instructors and seeing the smiling faces of our new sailors is very rewarding. And the sea is the most beautiful classroom in the world.” I couldn’t agree with him more as I sit on the deck in front of the Club House with a cup of tea in one hand and a book about nautical lore in the other. Looking up, I see a sleek cruising yacht unfurl its sails as it heads farther out into the channel towards the Bay Bridge, the horizon appears infinite, and it feels good to be alive.

[1] Thefirst all-sailboat, in-water show of its kind, the U.S. Sailboat show waswildly popular from its inception and by now it’s become one of the largest,most prestigious sailboat shows in the world, making a significant positiveimpact on the local economy. Boat show owner Paul Jacobs estimates they’ve paidthe City of Annapolis $20 million over the past 46 years just to lease the dockspace, and that’s not counting what the restaurants, bars, hotels, andretailers rake in from the party scene naturally generated twice a year whenhordes of sailing enthusiasts from all over the globe descend upon the colonialcapital. See https://www.capitalgazette.com/business/ph-ac-cn-sailboat-attendance-0504-20170503-story.html.If you want to join the party, go to Pusser’s Caribbean Grille for the “breakdown”at the end of the show where everyone gathers drinking Painkillers as they watchthe boats gracefully glide down Ego Alley and pivot into the harbor like runwaymodels. For a Painkiller recipe and more info about the tropical cocktail’slink to Chesapeake Bay culture, see https://chesapeakebaymagazine.com/chesapeake-cocktail-the-painkiller/

[2]Stephens was famous for designing the best competitive sailing yachts in theworld as well as amphibious vessels used by the U.S. Navy during WWII, whichearned him commissions to design boats for guys with beaucoup bucks and nameslike Vanderbilt, Rockefeller, and Disney. See https://sparkmanstephens.com/our-story/history/.

[3]The precise number of drunks is in dispute. John Cosby says it was 3, ananonymous source says it was 6, and this article says it was 4. https://www.soundingsonline.com/news/a-half-century-of-lessons-on-the-pleasure-of-sailing

[4] Forsome good Dowling quotes on the subject of the school’s mission to make sailingfun, thereby turning people on to sailing as a lifestyle, not just acompetitive sport, see  https://www.soundingsonline.com/news/a-half-century-of-lessons-on-the-pleasure-of-sailing 

[5]Case in point: for this year’s annual July 4th party (which was areally big deal because it was also the school’s 60th anniversarycelebration), Jenny chopped by hand what appeared to be 30 pounds of fruitsalad. It was delicious, btw.

[6] Children from the ages of 5 to 15 aregrouped with peers according to skill level. The 11’10’’ RS Zest trainingdinghies are the newest and smallest boats in the Kidship fleet. There are also16-ft catamarans for intermediate students who want to hone their skills and 12’Lasers for competitive racing for students at the advanced level aged 13-15.

[7] I attendedthe BLYS Summer Solstice Bash this year, which was held on a radiantly gorgeousJune 21.st For an admission fee of $35 for BLYS members and $45 fornon-members, you got your choice of beer, wine, or non-alcoholic beverages,scrumptious food by Grump’s catering, and live music by Guava Jelly. You couldshop at the local vendor tents or sign up for paddle-boarding classes taught byCapital SUP instructors as wells as yoga classes taught by BLYS instructors.The event closed out with a blissful sunset meditation and everyone was senthome with a goodie bag. What’s not to like?

[8]Nickname applied to the laid-back waterman’s neighborhood of Eastport byspirited residents who formed a tongue-in-cheek secessionist movement when thebridge connecting them to downtown Annapolis was closed for repair back in1998.

[9] Not to be confused with Davy Jones,Captain of the ghost ship Flying Dutchman. I don’t want anything to dowith that octopus-faced dude and his infernal locker.

[10]Someone told me that this rose petal proposal occurred on board one of theBeneteaus. Whether it happened romantic fantasy or reality is irrelevant. Youcould totally do it.

[11] Case in point: as I was interviewing Cosby for this piece, he briefly excused himself to "hand out high-fives” to newbie sailing students who had just docked a Rainbow for the 1st time.