The player assumes the role of Guybrush Threepwood, a young man who dreams of becoming a pirate, and explores fictional islands while solving puzzles.

Gilbert's frustrations with contemporary adventure titles led him to make the player character's death almost impossible, which meant that gameplay focused on exploration.

Via a point-and-click interface, the player guides protagonist Guybrush Threepwood through the game's world and interacts with the environment by selecting from twelve verb commands (nine in newer versions) such as "talk to" for communicating with characters and "pick up" for collecting items between commands and the world's objects in order to successfully solve puzzles and thus progress in the game.

[8] Like other LucasArts adventure games, The Secret of Monkey Island features a design philosophy that makes the player character's death nearly impossible (Guybrush does drown if he stays underwater for more than ten minutes).

[10] Guybrush meets several characters of interest, including a local voodoo priestess, Stan the Used Boat Salesman, Carla the Sword Master, a prisoner named Otis, and Meathook, whose hands have been replaced by hooks.

He promptly returns to Mêlée Island and gatecrashes the wedding, only to ruin Elaine's own plan for escape; in the process he loses the elixir.

[11][14] Gilbert soon realised that it would be difficult to design the game by himself; he decided to join forces with Tim Schafer and Dave Grossman, both of whom he hired for Lucasfilm.

[15] The game's insult sword fighting mechanics were influenced by swashbuckling movies starring Errol Flynn, which Gilbert, Schafer and Grossman often watched for inspiration.

They noticed that pirates in those films often taunted their opponents instead of attacking them, which gave the designers the idea to base the game's duels on insults rather than combat.

[11] Some of the dialogue was based on the designers' personal experiences, such as Guybrush's line "I had a feeling in hell there would be mushrooms", which came from Schafer's own hatred of fungi.

After having read Tim Powers' historical fantasy novel On Stranger Tides, he decided to add paranormal themes to the game's plot.

[13] Gilbert, Schafer and Grossman's primary goal was to create a simpler and more accessible gameplay model than those presented in previous Lucasfilm titles.

[11] He had previously applied his design ideas to the 1987 graphic adventure title Maniac Mansion, but considered he committed a number of mistakes during development, such as dead-end situations that prevented the player from completing the game and poorly implemented triggers for cutscenes.

[22] The team decided to make it impossible for the player character to die, with one notable exception, which focused gameplay primarily on world exploration.

The Secret of Monkey Island was the fifth Lucasfilm Games project powered by the SCUMM engine, originally developed for Maniac Mansion.

[24][26] According to artist Steve Purcell, that became a major limitation for the art team; due to a low number of "ghastly" colors, they often chose bizarre tones for backgrounds.

Guybrush would exclaim that there is an opening to a system of catacombs and attempt to enter, but this would result in a message stating the player needed to insert disc 22, then 36, then 114 in order to continue.

[32] LucasArts released a remake with updated audiovisuals titled The Secret of Monkey Island: Special Edition in July 2009 for iPhone, Microsoft Windows, and Xbox 360[33] exclusively via digital distribution.

While the team considered the SCUMM interface revolutionary at the time, LucasArts community manager Brooks Brown noted that it is incompatible with an analog stick, which most consoles use.

Brown had considered updating the reference to advertise Star Wars: The Force Unleashed because Loom was not on the market at the time, but concluded that the game would not be the same if such changes were implemented.

[52] According to Next Generation, The Secret of Monkey Island was a "relatively minor hit" in the United States, but the game and its sequel became "blockbusters on the PC and the Amiga throughout Europe".

[53] Hartley, Patricia, and Kirk Lesser of Dragon praised the designers' attention to detail, and cited the game's humor as a high point.

He noted that the game's plot and visual and aural presentation fit together to create a thick atmosphere, and finished: "Forget all those other milestone adventures (Zork, The Hobbit, Lord of the Rings et al) — for sheer enjoyment and general all-round perfection, The Secret of Monkey Island creams 'em all in style".

[54] Writing for The One, Paul Presley stated that "Lucasfilm appears to have taken all of the elements that worked in its previous releases and, not only incorporated them into this tale of scurvy swashbuckling, but even improved on them in the process!"

[46] Nick Clarkson of Amiga Computing cited the game's graphics as "flawless", noting that "the characters are superbly animated and the backdrops simply ooze atmosphere".

[45] Computer Gaming World said that "Monkey Island offers up LucasArt's famous humor at its best ... For an adventure you'll long remember, raise your cup of grog".

[57] In 1991, PC Format placed The Secret of Monkey Island on its list of the 50 best computer games of all time, calling it "genuinely funny".

[60] IGN named The Secret of Monkey Island one of the ten best LucasArts adventure games in 2009,[61] and ranked the Xbox Live Arcade version as the 20th best title of all time for that platform in 2010.

He cited its script, humor, plot, puzzles and balanced difficulty level as high points, and finished, "The Secret of Monkey Island: Special Edition is impressive, hilarious and downright worth your money".

[71] Justin Calvert of GameSpot noted that "the Special Edition looks much better and is the only way to play if you want to hear ... what characters are saying, whereas the original game's interface is less clunky".