The Ideal Sailing Event

Published on December 2nd, 2015

Albert Einstein defined insanity as doing the same thing over and over again and expecting different results. If that’s true, then Chris Smith must be the sanest person we know.

Smith, who lives in Tucson, is Commodore of the Arizona Yacht Club, and races his J/80, Sloop Dogg, at Lake Pleasant. He is also among the regulars at the annual Bitter End Yacht Club Pro-Am Regatta in October.

Held in the British Virgin Islands, Smith explains why he continually attends the Pro-Am expecting the same results…


It’s been 7 years in a row and I’m already signed up for the next one, the 30th edition. Add family vacations and I’ve been there 10 times. Let me put it this way. Why do saltwater salmon swim upstream? Why do Canadian geese fly back to, I assume, Canada? The Pro-Am has become, at least for me, a biological sailing imperative that is more than the sum of its many outstanding parts.

First, there’s something about arriving at a regatta by boat, especially when that’s the only way to reach Bitter End Yacht Club, whose resort and cottages line the beach and hillsides of Virgin Gorda along North Sound, one of the best sailing venues in the world. (Yacht Club Costa Smeralda apparently thinks so as well; it built a branch of its Sardinia-based club around the corner from BEYC.)

SMITHThe North Sound Express begins the transition to island time by picking up passengers in Trellis Bay, near the Tortola/Beef Island airport, and slipping through the Sir Francis Drake Passage past The Dogs (islands) and Spanish Town (no surprise here, a town) and then into North Sound where the iconic BEYC welcome building looms into view.

For a guy who started sailing 10 years ago, calls a lake in Arizona his home port, and lives 150 miles from his boat, the Pro-Am Regatta is an entre to racing with top tier pro sailors who I’d otherwise only read about.

Since 2009, that has meant sailing with, for example, legends Dave Ullman, Dave Perry, and Kenny Read, and young guns Taylor Canfield, Stephanie Roble and Sally Barkow, among others. (It would border on shameless name dropping to list all of the pros though I admit it occasionally is unavoidable in conversation to not say something along the lines of, “When I raced with Russell Coutts…”)

The “Am” part of the regatta is another reason I keep returning. Everyone is there to sail and have fun. The list of friends I have made at the Pro-Am keeps getting longer. It doesn’t matter whether I’ve gone solo or with my wife, there is always a place at a table. The Pro-Am has to be one of the most “inclusive” events in the sailing world.

There’s a reason the IC24 sailboat–a J/24 with a roomy J/80 style cockpit–is a staple on the Caribbean racing scene and the boat at the Pro-Am. It’s responsive and fun to sail in the trade winds, but when raced without a spinnaker, it accommodates sailors with wide ranges of experience and age.

A common complaint about sailboat racing is that it’s all windward-leeward. Racing with the pros at BEYC involved four formats in 2015: The Defiance Day Regatta–a point to point race from North Sound to the Baths and back, followed by fleet racing, team racing, and match racing in North Sound.

Sailing with different pros over the years also has provided the chance to ask questions and absorb as much as possible on everything from playing shifts along the shore (Russell Coutts) to team racing tactics (Taylor Canfield). As much as I hate the week ending, I can’t wait to get home and try new stuff.

And then there’s the local knowledge–Peter Holmberg introduced me to Cruzan Rum from St. Croix in the USVI. Cruzan and Mt. Gay, with rocks and lime, have become the cornerstones of the 100% effective Sloop Dogg Racing Anti-Scurvy Program.

While one of the pros will ultimately win the Pro-Am Regatta, there’s a regatta within the regatta for amateurs–the Scuttlebutt Sailing Championship. The qualifying rounds take place in Lasers, Hobie Waves, and Hobie Getaways and the top six qualifiers pick crews and then fleet race in IC24’s for the championship.

The talent runs deep, the starts are close, and mark roundings are tight, but Tom Leweck’s rule that protest hearings will take place at 3 a.m. on top of the hill above BEYC keeps anyone from getting too carried away. As if a virtual parking space in front of the virtual Scuttlebutt Sailing Club weren’t enough, the winning skippers also get free nights at the next Pro-Am.

I don’t want to give the impression that there are a lot of bars where they know my name, but when I stuck my hand across the bar at the Crawl Pub on the front end of the 2015 Pro-Am and said, “Hi, Toots, I’m…”, he interrupted me. “You’re Chris Smith.” Wow! My one-week-a-year neighborhood bar, 3,032 miles from home.

The same is true at the Watersports counter where Jerome, Jay, Javon, Sarah, Dobbs, Aaron, and the rest of the crew get to know you and make it easy to sail and SUP nonstop. My idea of the perfect day is taking out a standup paddle board and taking in a yoga class before breakfast, and then working in Laser and Hobie sessions before and after racing with the pros. Plenty of people, when not sailing with the pros, relax in hammocks or with their toes in the sand under palm trees, but with warm water and trade winds, and only a week to enjoy them, don’t stand between me and Watersports.

Going to the same restaurant day after day at home would be a recipe for madness, but the food at BEYC, including local fish and Caribbean dishes, is outstanding, and there is nothing routine about eating outdoors with the Caribbean a few feet away. And at the risk of sounding like the halyard that won’t stop slapping against the mast, when staff like Yolanda and Sherry Mae welcome you back, you know you came to the right place. It also says something about a resort that has had the same staff for years.

In addition to the “pluses” I mentioned, in the interest of complete candor and full disclosure, I must also say that BEYC has significant “minuses.” And they are among the reasons I keep going back.

There are no roads, no cars. Walking is the way to get around. The rooms do not have internet. There’s wi-fi at the restaurant, but once you get there, you’re likely to have actual conversations that go on for more than 140 characters and are a lot more fun. The rooms do not have TV’s. Eustachia Sound, with its hues of Caribbean blues and waves breaking on the reef, is always playing beyond the balconies of the Beach Front Cottages. And there are no elevators. Wooden stairs lead to the rooms, which are sublime in their simplicity.

There are undoubtedly plenty of tropical island resorts that offer sailing, but next October it will be time again for my annual migration to the BEYC Pro-Am Regatta.

NOTE: Scuttlebutt founder Tom Leweck must be pretty sane too. He first attended the Pro-Am in 2000 and has been there every year since.

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