Florida Keys

Caribbean Club, Key Largo

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caribbeanclub

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.”

 

Kayaking to Indian Key

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We always make at least one stop at bustling Robbie’s Marina in Islamorada (Mile Marker 77) on the way to or from Key West. We usually grab a bite to eat at the Hungry Tarpon Restaurant, feed the giant tarpon from the dock and wander around the quaint, open-air shops. However, last year we decided to rent kayaks from the Kayak Shack at Robbie’s Marina and take a kayaking adventure to Indian Key Historic State Park. After renting kayaks (we went solo, but the Kayak Shack also offers guided tours), we headed away from Robbie’s and under the Overseas Highway to open waters. Indian Key is only about a mile or so away, so it wasn’t too strenuous at all. Once we docked our kayaks, we wandered around the trails, checked out the historic ruins and climbed the wooden tower for a nice panoramic view of the surrounding area (we had the whole island to ourselves!). Indian Key has a fascinating and tragic history. In the 1830s, the island was the site of a burgeoning settlement established by a somewhat “ruthless” and “unscrupulous” wrecker named Captain John Jacob Housman (1799-1841). During the Second Seminole War in 1841, Housman and some other inhabitants of Indian Key were killed by Calusa Indians during a raid on the island (reportedly they had been tipped off about Housman’s offer to the federal government that he was willing to capture and/or kill all of the Indians in the area for $200 each). Housman’s grave is located on Indian Key and features the following inscription: “Here lieth the body of Capt. Jacob Housman, formerly of Staten Island, State of New York, Proprietor of this island, who died by accident May 1st, 1841, aged 41 years 11 months. To his friends he was sincere, to his enemies he was kind, to all men faithful. This monument is erected by his most disconsolate though affectionate wife, Elizabeth Ann Housman. Sic Transit Gloria Mundi.” Our kayaking trip to Indian Key turned out to be one of the most memorable outdoor excursions we have taken in the Florida Keys. Next time, we will set our sights on kayaking to nearby Lignumvitae Key Botanical State Park.

Burdines Waterfront Chiki Tiki Bar & Grille, Marathon

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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.

Schooner Wharf Bar

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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 …