I’ve been to Key West twice in my lifetime, but feel like I know it as well as any city I haven’t lived in. There’s a mystique that surrounds this old town, founded in legendary characters and salty songs. It was once the richest town in America until the Great Depression made it the poorest. Jimmy Buffet built this town back up, but so did Ernest Hemingway, and Tennessee Williams and the tourists who followed these characters to the end of A1A. Above all, Key West is a drinking town. And what goes better with drinking than music? Some of the biggest drinking towns also have the liveliest music scenes; Key West, Nashville, New Orleans, Austin.
The charm of Key West is partly its size – 4 miles by 2 miles, and partly it’s location as the southernmost point in the continental United States. But the laid back charm combined with all those other factors makes it magical. Key West is a tourist town, but it doesn’t feel like those other tourist towns a cruise ship might drop you off at. No hard press to buy this souvenir now! No barter culture that I detected.
Duval Street is a lovely stroll. A bar seemingly at every turn, and a guitar playing in just about every one of them. Hemingway’s house and the lighthouse across the street, having our token picture at the Southernmost Point, Mallory Square, the Old Seaport, sunset cruising, Fort Zac Taylor and swimming at the State Park were all highlight moments of course. But it was going with Kris that opened my perspective up quite a bit. I’m usually traveling alone for work, and we don’t have the opportunity to play tourist all that much as a family. Getting up early, driving to the airport and flying to Miami, renting a convertible and driving to Key West was a shared experience. We simply don’t have enough of those.
That drive from Miami to Key West is in parts beautiful, but in other parts ugly highway sprawl. But it was an adventure in both directions, especially when you look for stops along the way. We stopped for lunch on the way down, and at a bar and for Key Lime Pie on the drive back up. So Key West joins the Alaska cruise, the two Caribbean cruises, the Bahamas trip, Disney x 3, the Sedona/Grand Canyon trip and other trips for shared experiences. We need many more of these.