Spotlight reporter and self-confessed landlubber Jenny Jacoby set sail this month with the Coconut Grove Sailing Club, getting her feet wet on a sailboat for the first time as a volunteer with the club’s Moonlight Racing program.
All was emphatically not calm on Biscayne Bay as I headed out for my first-ever sailing experience on a recent Friday evening this month. A small craft advisory had been issued and 20-knot winds were ripping the bay.
This is going to be fun, I thought to myself as I rode out to meet my sailing companions for the night. I was joining the Mystique, a 26-foot sailboat, as a volunteer crew member for one of the Coconut Grove Sailing Club’s Moonlight Racing events.
The program – which introduces casual sailors to competitive sailing – takes place every month on the Friday closest to the full moon. It’s one of several initiatives sponsored by the club as part of its mission to get “butts in boats on the bay.”
Tom Cobin, one of the organizers and a race officer, told me the program “was designed to get people (sailors) who primarily cruise to get out and get a racing experience in a low-pressure environment.”
“It’s kind of a way to wind down after a busy week, and a great way, in my mind, to kick off your weekend,” he added.

The program was launched three years ago by Dave Martin, the club’s former commodore, but opened recently to volunteers like myself – no sailing experience or membership at the club required.
I pass Dinner Key Marina and the sailing club just about every day on my regular run, admiring the mooring field from afar as dozens of boats rock back and forth in the wind.
When an opportunity to actually get on one of those sailboats for free presented itself, I was completely on board.
The crew assembled on a beautiful, if windy, spring evening. Leading the boat was lifelong sailor Jacques Indekeu; second-in-command was Cobin with all of his race- manager materials. Then there was Jojo Bermudez, who gladly abandoned his shift at the club to fill the extra spot, and me – just happy to be there.
The sails were hoisted and we were on our way to the start line.
The strong winds (and overlapping Easter and Passover holidays) diminished the Friday turnout – only six boats would be participating tonight – but nothing could dampen my excitement.
Sailing, so central to the Grove’s identity, was something I had never experienced. But all that was about to change.
The Mystique, rated as the slowest of the boats in the fleet tonight, was first to set off, on the dot at 7:00 p.m.
As I soon learned between shouts to adjust the sails, the “pursuit” style of racing staggers each boat’s start time based on speed, allowing a mix of vessels to compete on an equal footing. It would be another 25 more minutes until the fastest boat began.

Once we set sail it became clear just how inept I was on a sailboat. Despite growing up on the water and spending time on powerboats – scuba diving and fishing – I had no idea what these people were saying. Sailors speak an entirely different language from the rest of us thalassophiles, making the sport’s learning curve very steep.
With such strong winds, there was not a lot of time for explanations, nor room for error.
A lingua franca of sorts was established with words like “duck” and “move.” It also did not take me long to catch on to new phrases such as “tacking” – a maneuver to change direction – which requires you to quickly switch to the opposite “windward” side of the boat.
I also learned if you’re not paying attention, falling off a sailboat is a very real possibility, as the boat heels (tilts) aggressively to one side or the other in the wind.
Luckily, I was sailing with skipper Indekeu, who described himself as a “do-your-own-stunts kinda guy.” He did nearly all the heavy lifting, letting his crew leisure about.
My only useful roles were to 1) move out of the way as instructed; 2) hold up an iPad for navigation check-ins; and 3) pass around beer (a more difficult task than expected when the boat is nearly sideways).
I was proud “rail meat” – the term for people on a sailboat who have no real purpose other than not throwing off the balance – giving me all the time to stare at the sunset melting into the Grove skyline.
“You didn’t see nothing, okay?” Cobin told me later when we were back on dry land.

“There’s a lot of choreography and teamwork in a normal race. You just did not see a hint of that because of the nature of the boat that we were on and the skill of the skipper sailing.”
If it were his boat, he explained, it would have been all hands on deck.
Getting thrown into the deep end is part of the experience of Moonlight Racing, even for those who come in with a solid sailing background.
“Imagine being a weekend jogger then trying out for a marathon, that’s the difference between sailing and those moonlight races,” club member Justine Deresz said.
Deresz sails frequently, volunteering with Team Paradise Sailing, but has only raced a handful of times. Friday was her third Moonlight Race.
“I’ve learned so much in the three times that I’ve gone out. People have been so willing to offer their insight,” she said. “You just have to be a better sailor to do well in racing. So, it’s a new challenge.”
Though the only prize is bragging rights, and the event is far from a full-scale regatta, the race brings out the club’s competitive side.
Throughout the 90-minute race, Cobin and Indekeu strategized how to fend off the boats chasing down the Mystique, constantly adjusting the sails to push the boat to its top speed of six-and-a-half knots and trying to gain an edge while cutting around markers.
As we sailed downwind into the final stretch of the race, darkness settled in. Though no moon came out, I could not take my eyes off the Brickell skyline, mesmerized by the city’s lights sparkling on the lapping waves – a scene that never gets old.
With a few beers and the realization that we would not be winning the race tonight, the mood grew calmer, and we chatted the remainder of the way back to the mooring ball.
Dare I say I felt like a real sailor?
Cobin told me that’s why he does what he does.
“My joy is to see people learn and grow based on what I can give to them,” he said.
“Doing this as a means to get people out on the water, in ways that – let’s face it – many people just don’t have access to, is one of the magical things (about) the Coconut Grove Sailing Club,” he added.
The club’s Moonlight Sailing program has been well received over the past three years, Cobin told me.
As I walked up to the club’s bar afterward, that much seemed obvious as participants recounted the race like sports commentators. Some even celebrated a high-place finish with a beer.
Now, as I go for my daily runs along the water I won’t be wondering what it’s like to be out on one of the sailboats. Instead, I will be wondering how soon can I sign up for next month’s race.
Editor’s Note: Those hoping to join Moonlight Racing can check in with the Coconut Grove Sailing Club to get on the email list for the monthly sign-up sheets. To contact the club, follow this link, or call 305-444-4571. The next three races are scheduled for May 1, June 12 and July 10.
















