Billed as “A Sunny Place for Shady People,” the Green Parrot Bar is one of my favorite Key West dive bars.
As a student at Stetson University during the mid-1980s, I would often join a ritual mass exodus off campus each Friday afternoon after classes to a somewhat rundown but lively fish camp overlooking the St. John’s River just off State Road 44 that we called Otis’s and the locals referred to as Sloan’s (both names derived from then-owner Otis Sloan). There we would spend hours hanging out on the dock drinking cheap beer and watching the boats slowly drift by – great memories! According to a September 2, 1998, Orlando Sentinel article, Sloan and his wife Myrtle opened the Shady Oak Fish Camp in 1957. I passed through DeLand in 2015 and took the above photos of Otis’s and it looked pretty much the same as I had remembered it. The Shady Oak Restaurant, which is located at 2984 West New York Avenue just west of downtown DeLand, reportedly suffered a fire in 2017 but has fortunately reopened.
According to its official website, the Caribbean Club was opened in 1938 by legendary automotive and real estate promoter Carl Fisher “as a poor-man’s fishing retreat.” It later became a gambling den. The bar served as a filming location for exterior shots from the classic 1948 film Key Largo, which was directed by John Huston and starred Humphrey Bogart, Lauren Bacall and Edward G. Robinson. The photo above was taken by legendary commercial photographer Joseph Janney Steinmetz (1905-1985). The Caribbean Club is the oldest bar in the Upper Keys. Today, the bar offers “live music, daily happy hours, waterfront sunset views and a dog-friendly atmosphere.” Ideally located at Mile Marker 104 bayside, it is open 7 AM to 4 AM “every damn day.” Note: The Caribbean Club is a cash-only bar with an onsite ATM. The bar served as a filming location for the Netflix original series, Bloodline. According to Jimmy Buffett, “It was a bar like many others and then it wasn’t.”
Tucked away from the Overseas Highway (Mile Marker 49.5) on a high deck overlooking the Boot Key Harbor Waterway, Chiki Tiki is an extremely laid-back, open-air bar and grill with a diverse menu that offers something for everyone. Highlights include certified Angus beef burgers (the green chile cheeseburger is a favorite!), shrimp baskets, blackened fish sandwiches, bacon wrapped BBQ shrimp, fresh-cut fries and much more. It’s the perfect place to grab an ice-cold beer or your favorite cocktail and enjoy the ocean breeze. Save room for the delicious key lime pie. Chiki Tiki features live music Wednesday and Friday nights. To reach Chiki Tiki, go East onto 15th Street in Marathon past an old trailer park to 1200 Oceanview Avenue.
A legendary Florida Keys singer-songwriter, Michael McCloud has performed at some of the best dives in Key West, Florida. McCloud knows more than 3,000 songs (his all-time favorite is “Somewhere Over the Rainbow”) and his own songs include such classics as “Tourist Town Bar,” “Conch Republic Song” (Key West’s Official “Secession” Anthem!), “The Hurricane Blows,” “Billy’s Bayou Barroom & Backyard BBQ,” “Today is the Day” (a moving tribute to the late, great treasure hunter Mel Fisher), “Peace and Quiet” (one of my favorite songs ever), “Just Another Song,” “Closin’ the Bars,” “Wild-Eyed Willie,” “Memorial,” “Most I Miss the Music,” “She’s Gotta Butt” and “Just Came Down for the Weekend” (which Jimmy Buffett has reportedly bought the rights to), among many others.
We first caught McCloud’s act back in the late 1980s. I believe he was performing at Sloppy Joe’s Bar at the time. I later heard that he had a falling out with Sloppy Joe’s management, which didn’t appreciate him hawking his cassettes. McCloud started referring to Sloppy’s as a “T-shirt shop that sells beer” or something to that effect. Then he moved on to Bull & Whistle, another great dive on Duval Street where he could sell all of his merchandise without any hassle. However, McCloud found his true home at the Schooner Wharf Bar (billed as “A Last Little Piece of Old Key West”), where he currently holds court Thursday through Sunday from noon to five (on Friday, Saturday and Sunday afternoons he is joined by talented musicians Captain Carl “Guitar” Peachey and “Professor” Pete Peterson on keyboards). So, if you’re ever down in Key West, take a little stroll off Duval Street and drop by the Schooner Wharf. Order some Tuna Nachos, which are simply amazing! Prepare to get a good buzz (I recommend the Rum Runner topped with a dark rum float!) and watch all your troubles slowly drift away …
Wandering Florida 