• Image about Dennis Conner
We are standing on the deck of one of the fastest sailboats on the planet and are about to embark on the race of a lifetime. This is a chance to experience the thrill of what it would be like to crew a yacht in the America’s Cup Challenge, a race featuring the oldest active trophy in international sport, preceding the first modern Olympic Games by 45 years. But what makes this 159-year-old event the ultimate experience for me is that I’m on deck with one of the finest captains I know: my dad. You see, this journey started off as a mission — a mission to find the perfect gift for a guy who seems to have everything. So, I connected with Troy Sears, co-owner of the Dennis Conner’s America’s Cup Experience in San Diego, and here we are.

Truth be told, this skiff is not the fastest sailboat on the planet today, but she is the fastest one I have ever been on. No small statement, considering I’ve sailed since I was in diapers. Her name is Stars & Stripes and she is, in a word, glorious. Weighing in at 50,000 pounds, her hull a striking 79 feet long and her mast 114 feet high (11 stories), she is an imposing and inspiring presence. To top it off, she was designed and built for Team Dennis Conner in 1994 and as such, carries the trademark name Stars & Stripes (as do all of Conner’s America’s Cup racing yachts).

Conner is to yachting what Michael Jordan is to basketball. The four-time America’s Cup–winning skipper is one of the most recognized names in the world of professional sailing. He won the cup in 1974, 1980, 1987 and 1988, earning the moniker Mr. America’s Cup. He also holds an Olympic sailing bronze medal, 28 world championship titles, four U.S. Yachtsman of the Year awards and membership in the America’s Cup Hall of Fame, and he’s authored nine books. Beyond his stellar accomplishments in competitive sailing, Conner is credited with being a driving influence in transforming the sport of yacht racing from amateur to international prominence.

Unlike other sporting clinics that don’t let you meet your hero as you learn the game, the America’s Cup Experience occasionally puts the world’s premier captain foursquare in front of you. Although The Man himself won’t be onboard with us this afternoon, we get the opportunity to meet with him prior to the race to pick up a few pointers. (This is another huge highlight for my dad, who positions himself to swap a few racing tales with the master and to get one of Conner’s books autographed. And to think I almost bought him another blue dress shirt instead!) Conner shares some insight on growing up in the sailing community in San Diego, which is geared toward racing rather than cruising. “In my youth I spent my days in and around the San Diego Yacht Club, learning from the best sailors in the world,” he says. “And that made all the difference. I have a life, better than I ever thought possible, doing exactly what I love to do every day. To top it off, the weather conditions here allow sailors to train year-round, so it’s ideal.” Then he offers a few pointers about the wind in San Diego Bay and issues a warning to watch out for the kelp beds that pepper the local waters. “They can slow you to a crawl.”

With that, Conner is off to prepare to race his wooden yacht, Brushfire, in a local regatta. In parting, he urges us to “enjoy your time out on the bay today, and remember: Second place is the first loser. I don’t like to lose, nor should you!”

Today we’ll be doing battle with the yacht Abracadabra, whose specifications are nearly identical to Stars & Stripes. She was designed and built for Hawaii’s Aloha Racing team and has a one-of-a-kind hull painted by marine-life artist Robert Wyland. Abracadabra is no stranger to the racing circuit, having competed in the 2000 America’s Cup. She beat Team Dennis Conner in the preliminary round that year but was unable to wrest the cup from the defender, Team New Zealand.