This game represents a HUGE step forward in the history of game design. Unlike almost all games of this period, players have two tokens, and a CHOICE about which to move, which affects how much debt they incur, and whether they get stuck into bad situations.
This game was designed by a woman known to history only as "Mrs. Shephard." This is the first game produced under license by Parker Brothers. (Source: _The Game Makers: the Story of Parker Brothers_ by Philip Orbanes)
The board is a stylized map illustrating activities which an American Tourist might engage in as they travel around Europe. The players start in the houses at the top left of the board, each with two tokens, and using a "spinner" or one or two dice, travel through the "shopping district", making purchases for their trip. Exiting the "shopping district", they take a cab to the Depot, and begin their trip on the railroad to the city. Some spaces have red dots, and include instructions that the players must follow, such as taking alternative routes (which can be shorter or longer than the main path), or moving to other red dots on the board, either forward or backward. Midway on the track (at the center of the board) is the "Centerville Depot" which a player must enter, and spend more for a meal. The end of the game has several water routes branching off from the railroad, which must be taken if they are landed on. If a player lands on another player on the railroad or a water route, the player landed on is sent back to the Depot.
The winner of the game is the first one to reach the end with both tokens, unless the second player reaches the end with both tokens, having spent less than half as much as the first player.