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Picture yourself teamed with Serena Williams or Roger Federer in the doubles final at the U.S. Open. Few, if any, sporting events in the world offer the fan an opportunity to participate at such lofty levels. The Bitter End Pro Am Regatta is different from any sporting event or regatta on earth. A world-class sailing event with 22 years of history, the Pro Am has matched up countless amateur and first time sailors with America’s Cup skippers, Olympic Medalists, Around the World Race Winners, and World Champions.

Due to its uniqueness, the Pro Am has been featured in the New York Times, the Financial Times, Sports Illustrated, Sail, Fortune Small Business, on the Fine Living Network, T2P.TV,  and countless other travel, lifestyle, and sailing publications. And the match-ups are for more than just a friendly daysail – egos are on the line. For the serious sailors in the group, it’s like a “Fantasy Camp.” For the non-sailors, it’s a chance to learn a new sport right at the top (imagine learning to play golf from Tiger Woods).

Previous sailing experience and athleticism are not necessary — desire and adaptability are. Experience the thrill of victory or grace in defeat. However, the Pro Am is not just about racing — it is also about fun. During your free time you can snorkel, windsurf, relax on the beach, or swim in the pool. An excursion to Norman Island or Anegada is always scheduled for Wednesday, the layday, which is devoted to non-sailing. One can join in, or just kick back.

In the evenings, “am” crew join our “pro” skippers for cocktail parties, wine dinners, Pub gatherings, organized Q&A sessions, and other social functions. The week is finished off with a rousing awards banquet, highlighted by prizes for the top teams, and great gifts for the rest of the group.

 In 1987 (the first year), the event was sailed in Lasers (fleet racing) and J-24s (match racing). From 1988 to 1998, Freedom 30s and a fleet and match race format were implemented. In 1999 we brought in the “Legends of Sailing” to triple race (Paul Elvstrom’s creative race format). For 2003 and 2004, the Masters triple raced Freedoms, and Juniors triple raced in our fleet of Hunter 216s. In 2005, Navigator-style racing was added to the course-racing program, and we will be repeating that in 2009. In recent years, we’ve used IC 24s (an improved J-24) for fleet racing. For 2009, Lasers, Hobie Waves, ICs, and Hunter 216s will all be used.