Abstract: A sailboat racing game comprises a game board having a grid pattern of interfitting connection means, and sets of sailboat representing playing pieces with complementary interfitting connection means. Each playing piece has a pair of interfitting connection means, e.g., pegs, to be interfitted in complementary holes of the grid pattern of the baseboard. The pegs of each playing piece are separated from one another by a characteristic distance, which determines the direction of travel of that playing piece across the board by interfit of the pair of pegs in the grid. Indicia are provided on the playing pieces, to indicate this direction of travel. A player determines his course of sail by selection of the appropriate playing piece. The separation of the pegs also determines the speed at which a given playing piece travels, since a playing piece moves a distance across the grid corresponding to its peg separation on each move.