Louie’s Backyard

Address: 700 Waddell Avenue, Key West

During the mid-to-late ‘70s, Jimmy rented an apartment here at 704 Waddell Avenue. The white building with the balcony railing on the left-hand side is now part of the Coconut Beach Resort.

The apartments have been updated quite a bit since Buffett’s days as a young songwriter, and are offered for sale as condominiums or timeshares. The building’s many porches and balconies overlook a pool area and private stretch of beach. It’s possible that the famous “front porch swing” mentioned in “Margaritaville” was at this very location.

Two doors down from Buffett’s apartment, you’ll pass Louie’s Backyard, a famed Key West dining spot mentioned in Jimmy’s song “Trying to Reason with Hurricane Season”. This is the Afterdeck Bar Jimmy referenced in his famously hungover lyric.

Back when Jimmy lived on Waddell Avenue, Louie’s was a very different spot.

Louie Signorelli turned his historic Victorian home into a small bar and restaurant in 1971. For over a decade, the spot only seated 12 and was managed by a single waiter. It was here that Jimmy would sing for his supper, racking up a meal tab that often went unpaid. In 1983 the restaurant was purchased and renovated into the establishment you see today.

Today, Louie’s has three distinct dining areas. The main restaurant offers a fine dining experience, with internationally-inspired food by veteran chef Doug Shook. The menu changes seasonally, so there’s always something new to experience. The Cafe at Louie’s offers panoramic ocean views and pairs fine wines and small plates for European-style dining. Menu highlights include fried artichokes and grilled octopus.

Louie’s Afterdeck Bar, located behind the house, offers their most casual experience. The deck juts out over the ocean, offering gorgeous views on three sides. The Afterdeck serves craft cocktails and fine wines, and you can even bring your dog! Louie’s serves a weekend brunch menu, complete with a separate cocktail menu; just like Jimmy said in the song, you can still stumble over to Louie’s Backyard for a Bloody Mary. After passing Louie’s, hang a right on Vernon and a left on South Street to reach our next stop.

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Songs to Play

• Trying to Reason with Hurricane Season
• A Pirate Looks at 40

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