KEY WEST. Captain Tony's is full of Key West history. The building was built in 1851 as a morgue, then it was converted to an icehouse and finally a telegraph station. This was the original location of Sloppy Joe's, and both Hemingway and Jimmy Buffet have been regulars through the years. Today the walls are decorated with underwear and live rock bands often play on Captain Tony's stage. If you want to sip a cold beer and hobnob with the locals, this is a great place.

Originally founded in Fort Walton Beach in the mid-70's, the Hog's Breath in Key West has been in business for almost 20 years. The bar motto is "Hog's breath is better than no breath at all" and this philosophy has been embraced by the regulars who come here to drink with wild abandon. In the fall, the bar hosts an annual home-made bikini contest. Live music is often on the menu and a raw bar provides snacks.

DUVAL STREET. How can you visit Key West without a stop at Margaritaville? Lunch and dinner are served in a restaurant decorated with ­ what else? ­ Jimmy Buffet memorabilia. Live bands play every night at 10pm and the margaritas are worth singing about.

Striped awnings and wooden tables and chairs lend this bar the feel of a poolside Caribbean retreat. Order a light lunch and groove to the tunes of the steel band. In the evening you can get supper while you enjoy jazz or mellow folksy music in the tradition of James Taylor or Key West son Jimmy Buffet. Smart-casual attire.

KEY WEST. A great waterfront location and nightly entertainment is what draws locals to this popular spot. A grill provides tasty eats but come to sit in the open air and sip a cocktail or beer. This establishment is "pet friendly" so don't be surprised to see a few dogs walking between the tables.