I never tire of Key West. I’ve lolled around the city at the bottom of Florida maybe a dozen times, each occasion too short. When I leave, I know I will be back.
It’s no secret that Key West is a part of America that moves to its own beat, one of those rare communities that seem out of country.
The so-called Conch Republic is the most Caribbean town in the United States. It’s an enclave for flamboyance and over-the-top celebrations of life. Folks who live here seem to revel in the outlandish personalities of many of their neighbors.
For visitors, Key West is a place to shed your mainland stresses and dresses, rules and jewels.
You read a lot about Key West’s bars, such as Sloppy Joe’s, and the local life and times of Ernest Hemingway — there’s a connection here — but I’m fascinated more by the legacy of another American who hung out in Key West.
You can tour the Harry S Truman Little White House, where Truman, perhaps our most Midwestern of presidents, grew to love the freedom and casual style of Key West. Truman was not a popular president, but in history’s review he keeps growing in respect.
Key West’s enclave on the water became President Truman’s place to get away from the noise and formality of Washington, DC. Here, he played a lot of poker and began each day with a shot of bourbon.
Views from the Island City House
I stayed two nights at the venerable Island City House, oldest operating guesthouse in Key West. It fronts on Williams street near the local library (free internet). Island City House is far enough from downtown’s Duval Street that the neighborhood is quiet and you feel almost like a resident of the Conch Republic. Island City House has no elevators though, so if you book a third-floor suite, with sitting porch ($180-$295), be prepared to lug your suitcases up the steps.
BTW, the best Cuban sandwich I’ve eaten was at Sandy’s Café, 1026 White Street, about a 20 minute walk from the downtown action on Duval St. The takeout joint is open 24 hours a day and is attached to the M & M Laundry, so you can eat well while your clothes dry.