Howie’s Lounge

howies-lounge
Address: Now the 5 Dollar Bar, 109 Duval Street

A classic stop on the early Buffett bar-hopping trail.

Now a souvenir shop, Howie’s Lounge was where Jimmy found his first steady job as a musician. While his first indoor gig was at a nearby spot called “Crazy Ophelia’s,” Jimmy considers Howie’s to be his first real job. At the time, Jimmy was working on the Petticoat III. The job at Howie’s gave him the exposure he needed to make music his full-time career.

Howie’s Lounge only employed women to work as its servers and bartenders, which proved an effective tactic for packing the bar full every evening. The tiny stage was in the front window and was almost entirely occupied by a grand piano belonging to local legend “Coffee” Butler. Though most of the crowd was there to drink and ogle the staff, music lovers would fight each other for the chance to sit by the stage and hear Coffee play.

Jimmy played the cocktail hour, from five o’clock to eight every night. According to the man himself, he’d play all day, go raise hell at night, sleep a couple hours, then get up at four in the morning to catch fish. Of his time at Howie’s, Buffett would later remember thinking, “I have got this made. This is pretty cool!”

Howie’s is also the spot where Jimmy first met a lifelong friend, writer Thomas McGuane. Continue on to the next stop to learn more about their enduring relationship.

 

Did You Know?
The building has hosted musicians, mischief, and margaritas since Jimmy’s early days.

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Songs to Play

  • Nautical Wheelers
  • Why Don’t We Get Drunk

Fan Tip: The bar has changed, but the energy? Still very Key West.
📸 Photo Idea:
Snap a shot in front of the “5 Dollar” sign—it’s a modern tribute to old vibes.

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