![]() Map thanks to Wanderlog, a trip planner app on iOS and AndroidĪlabama Jack’s is an old crab shack reminiscent of “old Florida” that consists of plywood and a tin roof. Once you leave Miami, it is about a 45-minute drive on US 1 until you reach a fork in the road – it is imperative at this point that you take Card Sound Road, which is the more scenic route and reminiscent of “old Florida,” and will also lead you to the first stop on the Itinerary, Alabama Jack’s. Mac’s Club Deuce, or to locals, “The Deuce” – a quiet refuge away from the madness of the Miami strip It is, I gathered, the oldest bar in Miami. If anything, it is simply a quiet refuge away from the madness and the oppressive heat of the Miami strip. It was Anthony Bourdain’s favorite bar in Miami, and you should go so you can find out why. The place is something out of a movie (actually a lot of the neon memorabilia is leftover from the filming of Miami Vice). If you happen to be staying one night in Miami – please, go to Mac’s Club Deuce. ![]() Or, if you have the time, drive back up to Miami from Key West and stop at some of the places you may have missed Book one-way ticket back to your home destination from Key West (for the day you plan to leave).Contact one of the car rental companies (Hertz, Turo app, etc.) in the Miami airport and rent a convertible, or similar vehicle in which you can take the top down (we rented a black Mustang Convertible) so you can truly feel and enjoy the experience (Seven Mile Bridge, etc.).Book one-way ticket to Miami, FL from your home destination, with an early morning flight departure (6am).One final recommendation: buy the Essential Book of Boat Drinks – you’ll thank me later. Two other great books that contain information about the early years and Key West are A Good Life All the Way and Jimmy Buffett: The Key West Years. ![]() You can find out more about the trip in Jimmy Buffett’s memoir, A Pirate Looks at Fifty, in which he describes the trip through the Keys as very “Kerouac-like” (author of the 1957 counter-cultural novel On The Road), and talking about what he felt at that time, which ended up being the trip that quite literally changed his life. Countless hours of research, phone calls, and e-mails have resulted in the creation of a “Buffett-inspired itinerary,” so you can follow in the footsteps of his first adventure through the Florida Keys and eventually, Key West in the early 1970s. He was the first road-tripper from Nashville all the way to Key West, taking notes on his observations, and of course, which places had the best grouper sandwich and ice-cold beer. However, I had never been to “Buffett Land,” also known as Key West. Augustine, Siesta Key, and eventually Englewood. My obsession with Jimmy Buffett and Florida started when I was a kid, road-tripping to Florida and stopping in Jekyll Island, St. I have received numerous inquiries in the past few weeks about the Florida Keys and Key West namely, because several friends and family members will be retreating to the United States’ southernmost island in February, March and April, and asked me for numerous recommendations, which ultimately warranted this blog post. – Jimmy Buffett A lone palm in Key West around 4:30 am sunset near Mallory Square looking out at Sunset Key ![]() “The days drift by, they don’t have names, all of the streets here look the same…there’s so many quiet places, smiling eyes match the smiling faces…I have found me a home”
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