You and a friend will get an exclusive, once-in-a-lifetime trip around Annapolis Harbor with America’s Cup sailor, NBC Olympics and ESPN commentator, and Emmy award winner Gary Jobson.

He will take the lucky winner on his sailboat Whirlwind around Annapolis Harbor, show off with a trip down Ego Alley, share inspirational sailing stories from his new book, give any aspiring sailboat racer some tactics advice and/or wow any novice sailors, and provide a view of the beautiful campus of the United States Naval Academy.

We will coordinate a mutually convenient and weather-dependent date for the winner and Mr. Jobson.