The object of Condottiere is to acquire four connected provinces in renaissance Italy. To do this players auction off different provinces on the board and bid on these provinces with a hand of cards representing mercenaries, seasons, scarecrows, and political figures.
However, unlike standard auctions in which only the highest bidder loses their bid, in Condottiere every player loses their bid. Players are, in effect, bidding the number of troops they are willing to lose in order to win a province. However, several special effect cards shake the contests up and keep the players guessing.