Jimmy Buffett Played At This Key West Dive Bar For The Drinks

A boatload of Key West tourists in search of a cold drink on a balmy day make a beeline to Sloppy Joe’s, an oft-crowded saloon that trades in Hemingway lore, as it was a favorite watering hole of the literary luminary. Those who’ve done a little more homework might head to Captain Tony’ Saloon, a cave-like bar that was formerly the first location of Sloppy Joe’s and also a Hemingway haunt. And if you’ve really dug deep into the Conch Republic’s repositories of revelry, you navigate your way to Chart Room for the dive bar’s relaxed vibe, to mix and mingle with locals, and for tales that sound tall but are mostly true.

The tiny, dimly lit bar is housed in Pier House Resort, a luxurious yet laidback property hemmed by Key West’s bustling Duval Street on one side and the ocean on the other, that first welcomed guests in 1967. The bar was not part of the resort’s original plan, but within weeks of opening, when someone asked where the bar was, the plan changed. A hotel room was hastily cleared out and turned into Chart Room, and little has changed in the almost 60 years since. These inauspicious beginnings belie the history the bar holds. Its walls and ceiling, covered in pinned-up faded dollar bills and amber-with-age photos and maps, have seen a lot.

It even helped jumpstart Jimmy Buffett’s career. According to “Jimmy Buffett, The Key West Years,” by Tom Corcoran, a longtime Chart Room bartender, after striking out in Nashville, the budding singer-songwriter made his first trip to Key West in late 1971. His first stop was Chart Room. The “island life” crooner kept coming back and was soon playing his music in exchange for free drinks to audiences that included Hunter S. Thompson and Jim Croce. Other celebrities rumored to be repeat guests include Truman Capote, Tennessee Williams, and Shel Silverstein.

The hangout drew more than musicians and writers. Key West’s elected leaders often used it as an unofficial office. One story claims that city hall phone calls were forwarded to Chart Room. Joe Dantoni, Pier House general manager, says that’s likely exaggerated, but he did verify local politicians spent a lot of time in the bar. “It was just the place to be! Many important things were decided over drinks at The Chart Room,” he says. The bar is even at the heart of a treasure hunt. Over rum and cokes, his drink of choice, Mel Fisher mapped out the search dives that led he and his team to the wreck of the Atocha, a sunken Spanish galleon. 

Some Chart Room patrons feel so at home, they never want to leave. So, they don’t. A close examination of the thick mahogany bar reveals small plaques bearing names like Panamah Peat (an employee of Fisher) and Bob affixed to its edge below pea-sized holes. The signs aren’t designating these folks’ favorite spots to sit—they’re minuscule grave markers. In each hole, under a plug to seal it, are the ashes of the deceased regular whose name is below it. 

Today, the Chart Room bar retains its dive-bar charm. Locals and past visitors have insisted it remain relatively untouched, and the resort has struck a balance, completing needed upgrades and décor refreshes to ensure it continues to provide an excellent guest experience, while leaving the bar intact. “We haven’t changed it much at all,” says Blanka Lamberson, the Pier House’s director of food and beverage. “We don’t want to and don't plan to.” Its traditions have survived, too. As they sip on Hemingway daiquiris and Sinking Treasure cocktails, Chart Room guests still snack on complimentary popcorn, peanuts and hot dogs, just like they’ve done for decades. 

Next time you’re in Key West, make a point to pop in Chart Room for a margarita or Thirsty Pirate (a semi-sweet, gin concoction) and drink in the history. But don’t be deterred by the lack of “Chart Room” signs as you approach Pier House. It’s just one more aspect of the bar that’s unchanged. “We don’t need to really advertise it,” says Dantoni. “It’s an iconic piece of Key West that people seek out.”