Wooden Ships and Iron Men is a naval board wargame in which the players simulate combat by sailing ships of the late 18th and early 19th centuries. The game was originally published by Battleline Publications in 1974 and republished by Avalon Hill in 1975, and is known as the definitive simulation of the period.
The game is played on a hex board with rectangular cardboard counters representing ships and long enough to cover two hexes, which represents the ship's orientation. Players write down their planned moves at the beginning of each turn, then move simultaneously (possibly entangling their ships if they are close to each other), fire their broadsides if any ships are within range, and attempt to board ships that are adjacent.
Wooden Ships and Iron Men is no longer being produced but Hasbro, which purchased Avalon Hill, has released the game as a free online promotional item. (quoted from the WS&IM Wikipaedia entry. )