In a matter of weeks, Margaritaville had its own tequila and beer brand.

The theme park Margaritaville has been a runaway hit since opening in 1999. Last year, according to Mr. Cohlan, the restaurant generated about $22 million in sales. Something about Mr. Buffett’s mellow, unchallenging persona seems to make parents feel O.K. about tying one on with their children in tow. “Believe me,” Mr. Buffett said, “I didn’t know I was going to end up as family entertainment, either.”

Not everything has gone Margaritaville’s way.

For starters, that early beer, Lone Palm Lager, named after one of Mr. Buffett’s songs, did not sell as they had hoped. “We only found out later, after we did consumer research to figure out what was going on, that the name bummed people out because it made them think about drinking alone,” Mr. Cohlan said. They renamed it LandShark Lager, a nod to Mr. Buffett’s song “Fins.” Ta-da: Sales started to take off.

The company’s first resort, a planned $700 million casino and hotel in Biloxi, Miss., was delayed by the late-2000s economic collapse. Margaritaville eventually opened a much smaller hotel in Biloxi, but it went belly up, perhaps because the company picked a bad location. This month Mr. Cohlan announced a third attempt, set to open later this year. This time, there will be more of a family focus, and no casino. Eight more Margaritaville hotels, including one in Grand Cayman, are in various stages of development.

Margaritaville’s signature restaurant chain is expanding quickly — it will soon push into California for the first time, opening at Universal Studios Hollywood — but a spinoff series of restaurants in the Midwest called Cheeseburger in Paradise has struggled. Margaritaville sold its Cheeseburger stake in 2005 and, since then, roughly half the locations have closed as the brand was lobbed between owners.

Still, Margaritaville has mostly had smooth sailing, building a unique corporate culture — employees all use the same valediction in emails: “Fins Up!” — and drawing fanatic customers like Carol and Butch Wayland, who live in St. Catharines, Ontario. The Waylands, who own a trade school, have made it their mission to visit as many Margaritaville outposts as possible; in May they plan to try their first Margaritaville at Sea, a new offering by Norwegian Cruise Line.

“We’re not Parrot Heads,” Mrs. Wayland said. “We’re just normal, everyday people who happen to be residents of the Margaritaville state of mind.”

Mrs. Wayland, who is in her 50s, added that she had “spent a fortune” on Margaritaville products, including hats, flip-flops, dress shirts, shorts, clocks, coffee mugs, barware, a blender and underwear. They also have a framed photograph of themselves popping out of a margarita-glass-shaped Jacuzzi, snapped at a Margaritaville location in the Caribbean.

If all of this sounds like maybe Mrs. Wayland sometimes has one margarita too many, she wouldn’t entirely disagree. “That too!” she said. “I once fell off a bar stool at the Margaritaville in Turks and Caicos and landed right in the water. Kerplop.”