Sid Meier’s Pirates! is a video game created by Sid Meier and developed and published by MicroProse in 1987. It was the first game to include the name "Sid Meier" in its title as an effort by MicroProse to attract fans of Meier's earlier games, most of which were combat vehicle simulation video games. The game is a simulation of the life of a pirate, a privateer or a pirate hunter in the Spanish Main in the 16th, 17th and 18th centuries.

The game was widely ported from the original Commodore 64 version. It was ported to the Apple II (1987), as a PC booter (1987), Apple IIGS (1988), Macintosh (1988), Amstrad CPC (1988), Atari ST (1989), Amiga (1990), Nintendo Entertainment System (1991), iPad (2011) and Windows Phone 7 (2012).

Pirates! is set in the Caribbean. The Pirates! playing field includes the Spanish Main (namely the northern coast of South America), Central America and the Yucatán Peninsula, the entire Gulf of Mexico, Florida, and all Caribbean islands including Bermuda. The player is free to sail to any part of the above mentioned lands, stopped by an invisible barrier southeast of Trinidad, all the way north to just northeast of Bermuda.

Pirates! was released in several different versions for the PC; the original 1987 game (which came on a self-booting disk), a 1989 DOS rerelease (otherwise functionally identical to the booter version), a 1991 release which came on high density floppies and only had the manual copy protection, and the 1994 edition which was a fully modernized CD-ROM game with VGA graphics. The 16-bit versions of Pirates! have an extra feature where governors assign you missions that was not in the 8-bit versions. A port for the Nintendo Entertainment System appeared in 1991, developed by Rare Ltd. and published by Ultra Games. Notably, tobacco is replaced as a trade item by "crops" because of Nintendo's family-friendly requirements.

Pirates! is a single-player, open world game. The player receives a letter of marque authorizing service as a privateer for Spain, the Dutch Republic, England, or France in the Caribbean. The player's loyalties may change over the course of the game; he may also hold rank with multiple countries and may turn to piracy at any time. Gameplay is open-ended; the player may choose to attack enemy ships or towns, hunt pirates, seek buried treasure, rescue long-lost family members, or even avoid violence altogether and seek to increase his wealth through trade. The game also has no predetermined end, although as time goes on, it becomes more difficult to recruit crew members. As the player character ages, fighting becomes more difficult, and deteriorating health will eventually force the character into retirement. The game ends when the player retires, at which point he is given a position in his future life, from beggar to King's adviser, based on accumulated wealth, land, rank, marital status, and other accomplishments.

The era of play is one of the choices given to a player at game-start. Different eras provide a different challenge, as political and economic power shifts between the four fledgling European empires. Choosing 1560 (the earliest choice) as the starting year places the player in a Caribbean almost devoid of influence but that of Spain, while 1680 (the latest choice) provides a mature Caribbean with many non-Spanish colonies and an overall higher degree of activity in the region. The other choices include 1600, 1620, 1640, and 1660, with progressive effect of reducing Spanish dominance in favor of the other nations, while increasing seafaring traffic. Ship designs are also era-dependent, with some types of ships appearing more frequently in certain eras and less in others, and certain ship types being used near-exclusively by certain nations.

The game tests a wide range of skills: hand-eye coordination during the fencing sections, tactical ability during the land and sea combat phases, and strategic thinking, for everything from choosing a wife to deciding when to divide up the plunder. Moreover, each game is likely to take a different course, as most events in the game are random, including the economic and political systems, and early in the game these can greatly affect future strategic options. In the course of the game a player may try to tack in a frigate in order to run down a smaller and faster pinnace, but must be fortunate enough to have the weather gage.

One of the most innovative features of Pirates! is the introduction of a dynamic playing field. In Pirates!, many of the most important factors which affect player decisions are randomized at the beginning of the game, and continue to shift during gameplay. This not only creates a new experience each time the game is played, but also requires the player to remain flexible, and be ready to exploit possibilities when they occur. The most important random factor in the game lies in the diplomatic relations between the four nations laying claim to the Caribbean. Relations may differ greatly from game to game, and can shift in an instant, creating and removing opportunities, possibly even for long periods of time. The player generally benefits from periods of war between two or more countries, because any aggression towards a country's ships or cities, which occurs often if not specifically avoided, will gain recognition with its enemies, prompting them to bestow the player with land, titles, and other benefits. During peacetime, the player can only benefit from the capture of pirates on the high seas, which is seen as favorable by all nations, but is a rare occurrence. Cities are also dynamic, with statistics like wealth and population fluctuating constantly. The player has a list of cities in one of the game's menus, allowing him to see the statistics of any city. Some cities will show accurate statistics, especially if recently visited. Other cities may be colored differently on the list, and will show no data. This indicates that a city's statistics have changed since the last visit. Visiting taverns in cities may yield an encounter with a traveler who offers to tell information about cities whose statistics have changed. Knowing the statistics of a city helps the player plan ahead, especially with regards to trading or any desire to raid or conquer cities. Changes occur whenever time is passing, and are unrelated to player actions. In fact, in this earliest game in the series, random events do not have any graphical representation, and the player can do nothing to prevent them.

The original versions of Pirates! sported both disk and manual copy protections. Users are asked the time at which various treasure ships are arriving at port. If the time is wrong, the game will continue, but at a much higher difficulty level that would frustrate most people.