Key West is forever tied to the music of Jimmy Buffet, who championed the concept of a sunshine- and margarita-soaked getaway. While this favorite son’s tunes waft from shops, restaurants and bars across the Keys, there are plenty of musicians who have followed in Jimmy’s footsteps, playing their own brand of music for locals, tourists and vacationers.
Best Places to Hear Live Music in Key West, Florida
Among the best places to hear music in Key West is Schooner Wharf. This classic waterfront setting is located at the foot of William Street, on the Historic Harbor Walk. Schooner Wharf treats its patrons to live music seven days a week: single acts, duos and bands. Music starts at high noon and, after a short break from 5-7 pm, goes until eleven or twelve at night. If you’re headed to Key West during a vacation to Marathon, Schooner Wharf is the first and last place you should stop. It’s that awesome.
The late Charles Kuralt said Schooner Wharf “must surely be the center of the universe” and it’s been written about in the New York Times. A second floor deck offers seaport views of yachts galore. Occasionally a famous musician will pop in to play, surprising lucky patrons on a Florida Keys vacation.
Rick’s Bar, at 202 Duval, often has professional vocalists starting at 4 pm but occasionally gives comedians this time slot, too. Part of a giant entertainment complex of 8 venues and 13 bars, Rick’s is probably best visited by cab… you never know where the day or night will lead. Durty Harry’s, in the same complex, serves up live rock & roll in a sports bar atmosphere. If you get hungry, no problem: you’re surrounded by Key West restaurants.
The Green Parrot Bar
A little more off the beaten path is the inviting ambiance of The Green Parrot Bar. Called “the definitive Key West Saloon” by a travel writer for Playboy magazine, this worthy destination is found on the corner of Whitehead and Southard. You’ll love the historic building, circa 1888, which houses this locals’ favorite, and you won’t be alone: the Green Parrot Bar has been serving thirsty Key West residents and vacationers who are in the know since 1948 (prior to that it was a grocery store).
It might be impossible not to enjoy yourself in a bar that has the slogan “No sniveling.” But the live music is definitely one of the main draws at this friendly, eclectic establishment. Rock, blues, bluegrass or rhythm and blues could be the order of the night. The quality of the music is high; the dress code is pretty much “anything goes.”
The Green Parrot’s music schedule is a little quirky; check online, call or just pop in to see what’s happening when. Weekend nights (and perhaps others) draw a very diverse crowd. Keep your eyes open and you might spot a few subtle surprises unlike those you’d see in, say, Toledo.
El Meson de Pepe
If you want to hear some Latin music during your vacation, then head for the patio bar at El Meson de Pepe, on the north end of Mallory Square. This relaxing spot, shaded by an over head canopy, is the perfect place to sit and sip a mojito or peach margarita, while listening to the island’s only salsa band.
Part of a family-owned Cuban restaurant which has been open for over 20 years, El Meson (or Pepe’s, as locals call it) is housed in one of the most fascinating spots in the Keys. The “Cayo Hueso y Habana,” building is situated on the exact site where thousands of refugees from Cuba disembarked on American shores during the 19th century.
You’re also likely to come across a variety of buskers (performers playing only for tips) in Key West, but these are some sure bets for great live entertainment.