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).