This was also the first Larry game to receive an ESRB rating upon its original release.
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 Seller'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).
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.
Leisure Suit Larry: Love for Sail! utilizes a single-icon point-and-click interface. Left-clicking on an interactive object pops up a menu with verbs specific to that subject. The "Use" menu allows the player to use any item from their inventory on the object. “Other...” provides a text box where the player can type in their own verb or subject, which is needed to unlock several Easter eggs.
It was also the first Larry game to include a full-fledged minigame (not counting the casino games in the earlier installments, which were essential to the plot): collecting hidden red-and-white-striped dildos (Where's Dildo?, a pun on Where's Waldo?) is one of three goals required to unlock a dirtier ending and a bonus wallpaper.
If the player's desktop wallpaper is set to the WALLPAPR.BMP file included with the game, it will change to a high-quality pin-up desktop wallpaper of the last lady Larry "conquered" (the images are simply Windows BMP files stored in the Drivers subdirectory of the game under misleading Memory1.drv ... Memory8.drv names; they can be opened with any graphics program).
Unlike the previous Larry games, Larry cannot die or get stuck due to a bad decision.
A harder game mode can be accessed by putting a file named "GET_HARD" (without an extension) in the LSL7 directory. In this mode, most key conversation topics will disappear, so the player will have to type them in with the "Other..." menu.
Players could also "appear" in the game by placing voice samples of selected dialogue and a digitized photo in a particular directory (the default was Al Lowe). Due to time constraints, the information to do so was not printed in the manual, but was published only some time later in an on-line announcement.
Love for Sail! also provided a more-literal-than-usual interpretation of Easter eggs: when certain obscure actions were performed, a small icon resembling an Easter egg flashed in a corner of the screen. This usually indicated that a "seduction" scene could now be played featuring nudity that was normally obscured.
Due to the lack of documentation, and the obscurity of the totally unguessable easter eggs, all these were possible only after following the hints released by the Sierra website, several months after the release of the game.
The game also shipped with a "CyberSniff 2000", a sheet of numbered scratch-and-sniff paper, corresponding to a number displayed on the screen at a certain location, so that the player could get a scent of what the area the player was in smelled like.