• Image about Dennis Conner
Since 1851, the America’s Cup has been a challenge-driven series of races between the current owner of the cup, known as the defender, and the hopeful owner, known as the challenger. In other words, much like the Victorian forge in which the cup was shaped, and just like the men of honor of the antebellum South who settled disputes in duels, a cup race comes together after the champion is challenged. Because we are sailing one of Conner’s yachts, we have naturally concluded that we are the defender for today’s regatta. Although a storied ship, Abracadabra will be the challenger.

Each yacht is equipped to handle up to 20 crew members participating in the clinic, in addition to a provided captain and three to four professional support crew. As we board Stars & Stripes, Sears sums up the talent for the day and finds that our crew is a typical mix. About half have never sailed before, with the balance being an equal number of novice and advanced sailors — an intriguing mix of talent, enthusiasm and wonder. “I approach this business from a sailor’s point of view,” Sears says. “We are informal. We are dedicated to having fun, and we set sail with the expectation of winning. It is a privilege to expose you to sailing if this is your first time. If you are one of my more experienced crew members today, there is a good chance that this yacht is quite a bit different from what you have sailed on, so it will be a fun learning experience for you as well.”

The America’s Cup Experience allows its participants to do as much or as little as they desire, even though the endgame is to win. If you want to kick back and enjoy an afternoon in the bay, taking in some sun while dancing across the water, there are several suitable spots. If you are looking to hoist the mainsail, work the grinders or even take the helm, those opportunities are yours for the asking. “Here is the best part for all of our first-time sailors: Our yachts are so large and stable that we offer our no-seasickness guarantee,” Sears says. “If you lose your lunch, we will replace it. Now let’s win this thing!”

We’ve had the pep talk. Stations are assigned. Each yacht hoists her sails, glides into the bay and gets into position for the moving start. The sun’s rays intensify the farther we get from shore, while the temperature tops out in the upper 70s. It’s punctuated by light coming at us from all directions, reflecting off the water, off the white mainsail, off the deck. And the wind is blowing out of the north at 11 knots. In sailing parlance, this is a perfect day.

Each boat and crew hurriedly works its way into a starting position. The key here is to build the yacht up to full speed, timing things so the boat hits the starting line at the moment the starting gun fires. If you cross the line too early, you must circle back behind the starting line and cross it again — a real time killer and a guaranteed way to lose the race.

My dad and I quickly become familiar with the gear speeds on the winch, which is the drum-shaped piece of deck hardware used to adjust the sails and which is controlled by a hand crank operated by two people known as grinders. The navigator is plotting the best course, and the tactician is checking the sails and the sheets to ensure that we reach the start line at the precise moment. The timer is barking out the countdown of the final minute before the start. After some maneuvering, we begin to close in on the start line. This not only gives us the feel (and tension) of a real America’s Cup start, but it also offers the guests at the Maritime Museum of San Diego, today’s starting committee, a better understanding of how a sailing race works. We feel the tension as we jockey for the best position at the start. The gun is fired, and we cross the line just behind Abracadabra. The race is on. Conner’s words are front of mind for all of us. The wind conditions are exactly as we were told, kelp beds are being watched, and the “second place is the first loser” mantra has us racing scared. After all, we don’t want to disappoint The Man.