A game of chance and skill based on the America's Cup theme. For two to four players. The object of the game is to be the first player to complete the eight leg race. "Race for the Cup" will challenge the yacht racing enthusiast, educate the sailing novice, and prove entertaining for fan of the sport of sailing. The board is a cloth with squares marked on it. There's a triangular race course printed on it. The pieces/sailboats move around the course, square-by-square based on a die roll and playing cards. There are card for the Start that might give a player some advantage or hindrance; Upwind cards for that portion of the race, and Downwind cards for that portion. A card is taken by the player at the start of their turn and played immediately. The players race around the course 8 times and the first to finish is the winner.