Dave grew up in Connecticut sailing Blue Jays and Lightnings at the Pequot Yacht Club on Long Island Sound. He received his undergraduate degree at Yale, and has received an honorary Doctorate of Education from Piedmont College. He is a Senior Certified Judge, and has been a member of the US SAILING Appeals Committee since 1986, and is currently the Chairman. He has authored three books on the sport, Understanding the Racing Rules of Sailing, Winning in One-Designs, and Dave Perry’s 100 Best Racing Rules Quizzes.

At Yale he captained the 1975 Dinghy National Championship Team and is a two-time All American sailor. He was fifth at the 1979 Laser World Championship, two-time Congressional Cup winner (1983 & 1984), second in the 1984 Soling Olympic Trials, the 2003 Ideal 18 North American champion, and three-time U.S. Match Racing Champion (in 1982, 2006 and 2008!).

He is a member of the Sailing World Hall of Fame, the recipient of US SAILING's W. Van Alan Clark, Jr. Trophy for Sportsmanship and the first recipient of the Captain Joe Prosser Award for Excellence in Sailing Instruction. He has conducted thousands of "rules talks" and seminars on the sport, and is best known for his clear, humorous and highly interactive presentations. He was the Rules Advisor and Afterguard Coach for Victory Challenge 2007, Sweden’s America’s Cup team; and the Rules Advisor for the 2008 U.S. Olympic Sailing Team in China.