Leisure Suit Larry: Love for Sail!

The plot revolves around Larry's attempt at winning a weekly contest held on the ship by Captain Thygh, a gorgeous blonde. The contest involves a series of other games varying from legitimate sports competitions like bowling to naughtier things like a machine created to test one's sexual prowess. Each passenger is given a score card with a selection of the various competitions to compete in, and the passenger with the highest cumulative score at the end of the week wins. The prize is an additional free week on the cruise spent sharing the Captain's cabin (and, presumably, her bed.)

The player must come up with a variety of ways to cheat in each of Larry's assigned competitions so that he can get the highest score and win the contest. Among Larry's chosen competitions are a cooking contest, a "best dressed" contest, a game of horseshoes, bowling, the sexual prowess contest and others. At times Larry wins these contests not by cheating but only by an unexpected twist of fate triggered by his (often unintentional) actions. For instance, Larry's encounter with fashion designer Jamie Lee Coitus causes his Leisure Suit to become the height of fashion; as such he wins the best dressed competition. Similar to Leisure Suit Larry 5: Passionate Patti Does a Little Undercover Work, it is impossible for the game to be placed in an "unwinnable" state, by a bad decision.

Love for Sail! was the first Larry game since the third to pick up immediately where its predecessor left off; typically, it features Larry getting dumped by the woman who represented the ultimate goal of Larry 6, Shamara.

The formula was much the same as the previous games: the "twist" was that Larry was a passenger on a cruise ship populated by parodies of famous people. Among the other cruise guests were "Drew Baringmore" (Drew Barrymore), "Dewmi Moore" (Demi Moore), "Victorian Principles" (Victoria Principal), "Jamie Lee Coitus" (Jamie Lee Curtis), "Nailmi" and "Wydoncha Jugg" (Naomi and Wynonna Judd) and "Annette Boning" (Annette Bening). Various other pop icons were parodied in the background, such as the Archie Comics gang playing nude volleyball, various incarnations of James Bond in the ship's casino (itself an homage to Peter Sellers's famous Casino Royale parody), a Sierra staffer dressed as Sailor Moon, and porn icon Ron Jeremy walking around naked. Most of the male supporting cast (Peter the Purser, Johnson the bartender, Dick the guardrobe attendant, Wang the galley server, Bob Bitt the artist) are named after popular euphemisms for the male reproductive organ or are in some way related to it (Bob Bitt, for instance, is named after John Wayne Bobbitt; the character also shares the same first name and bears a passing resemblance to fellow artist Bob Ross).