Objective Havana is an operational level, solitaire simulation of the planned-but-never-executed US invasion of Cuba in late 1962. The premise of the game is that President John F. Kennedy had ordered the US military to invade the island in order to remove Soviet missiles and nuclear weapons. Historically, the missiles were removed by a combination of American military and diplomatic pressure (known as the Cuban Missile Crisis), but the game looks at the "what if."

The player controls the US forces; the game system controls the opposing Communist reaction. The objective of the game is for the US to capture Cuba at the lowest possible cost in casualties.