Key West nightlife means the rhythms of reggae, salsa and island rock spilling from the open doorways of clubs and saloons, the whirr of a blender as a bartender concocts a perfect frozen margarita, and the laughter and clink of glasses as new friends toast the evening’s promise.
Especially on lively Duval Street and in the waterfront Historic Seaport, the Key West scene really heats up once the sun goes down. You might sip a tall cool drink at an outdoor bar on Lower Duval, wander into a sultry jazz club or wine bar, or stop by a seaport tavern where regular patrons’ pooches enjoy their own “cocktails” — bowls of ice water.
So where do hearty partiers go? One popular spot is Rick’s/Durty Harry’s Entertainment Complex at 202 Duval St. Its eight venues include the Tree Bar featuring laid-back bartenders and premium spirits, a contemporary dance club dubbed Rick’s Upstairs, the upscale Rick’s Loft specializing in signature martinis, and the live rock hotspot known as Durty Harry’s.
Jimmy Buffett, the famed singer/songwriter/author who honed his creative chops in Key West, also operates a bar and restaurant on Duval Street. The island is credited with inspiring his hit song “Margaritaville” among others — and Jimmy’s Margaritaville Café, located at 500 Duval, offers tasty casual food, cocktails and great music by performers including his musical friends and band members (and occasionally JB himself).
Back in the day, Jimmy was a regular at the Chart Room at the Pier House Resort, 1 Duval St., a hideaway where Key West movers-and-shakers plotted and partied in the late 1970s and early ‘80s. Venture inside today for what Chart Room bartenders still call “a sensible cocktail,” and you just might hear a hint of their long-ago laughter.
Many notable musicians and performing songwriters favor the Smokin’ Tuna Saloon, 4 Charles St. The mostly open-air establishment features quality bands that showcase a wide range of musical stylings. The Tuna is also headquarters for the nationally acclaimed Key West Songwriters’ Festival, which brings more than 100 chart-topping songwriters to the island each May.
While Jimmy Buffett and other songwriter-musicians draw music fans to Key West spots, another favorite son left a different kind of legacy at two local bars.
Legendary writer Ernest Hemingway spent most of the 1930s on the island, penning fiction that changed the face of American literature — and hanging out with friends like saloonkeeper Joe “Josie” Russell at his Sloppy Joe’s Bar.
Josie’s bar was located at 428 Greene St. until a rent dispute caused him to move it around the corner to 201 Duval St., where it’s now an internationally known watering hole. Each July, Sloppy Joe’s hosts the “Papa” Hemingway Look-Alike Contest — and visitors flock to the place year-round for its live entertainment, ample drinks and Hemingway heritage.
Josie’s original Sloppy Joe’s is now called Captain Tony’s Saloon after another colorful former owner. The late Captain Tony Tarracino was a gambler, gunrunner, charterboat captain and Key West’s one-time mayor. Bar patrons enjoy live music and cold libations surrounded by offbeat memorabilia.
A few blocks away at 601 Whitehead St. stands the ramshackle Green Parrot Bar, which dates back to 1890. It’s characterized by easygoing bartenders and eccentric atmosphere (including signs reading “Sorry, We’re Open” and “No Snivelling”). The self-proclaimed home of great drinks and bad art, the Parrot also offers jazz-, funk- and blues-infused entertainment.
Another hub of Key West’s lively nightlife is the Schooner Wharf Bar, located in the Historic Seaport at 202 William St. The bar began its life on an actual schooner, but later moved ashore to its open-air waterfront setting.
Owner Evalena Worthington and her welcoming staff have made the Schooner a locals’ favorite known for its live music, funky charm and events like an annual holiday boat parade and a wacky “minimal regatta.”
In fact, whether you’re seeking seaport shenanigans, island rhythms or the chance to attempt the “Duval Crawl” of main-street establishments, Key West has what you’re looking for. So come on down and enjoy our nightlife for yourself!