Condottiere is one of my favorite card and board games. The action takes place in late medieval/early Renaissance Italy and the players assume the role of the great mercenary captains of the age. I can't honestly say that I know for certain this game captures the feel of the period, but it seems so to me. Armies of dubious loyalty dominate the scene, but the Church, courtly politics, and a few idealistic warriors/zealots play a big role as well.
The game board is a map of Italy, divided into numerous regions. Each player displays control over a region with old-style painted wooden cubes. The results of battles, won and lost through hands of cards, determines who wins a province and who determines where the next battle will occur. Despite the focus on battles, the heart of the game is bluffing and sneakiness. The strongest player - in terms of military power alone - may not necessarily win a game. You got to know when to hold 'em and when to fold 'em. Players achieve victory by controlling a set number of provinces according to the number of people playing; the required number of provinces are fewer if they share boundaries and form a contiguous whole.
Card play takes the form of hands which represents a battle (or campaign) over a region of Italy. Cards mostly take the form of mercenary units, but mighty heroines (a la Joan D'Arc), bishops, courtesans, drummers, and the weather appear as well. Generally a player wins a battle by having the strongest army in play when the last card is played.
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