Shops fashionable and funky line Key West’s Duval Street ; photo by Dreamstime
Key West, Florida is more than a place. It's a spirit, a funky energy that enters your soul and takes residence in your worldview as well as your inner vision. A state of mind more than a city; a way of life more than a place to live. It’s a lifestyle as much as a destination. All expressed in the absurdist poetry that is Key west, a language not spoken anywhere else in the country.
But even recognizing all this, I didn’t fully have a grasp on the essence of this city until I spotted several elderly men playing Bocce ball. I asked another observer if lawn bowling is popular because many people of Italian descent live in Key West. “Oh no,” she chuckled. “It’s popular because you can play bocce with one hand and hold a drink in the other.” Welcome to Key West!
Turn a corner on a nondescript street or pass a random restaurant, and strands of guitar riffs assault your ear drums. Either that or a rooster crowing. Actually a lot of roosters – they’re everywhere.
The oldest house in Key West dates back to 1829 Photo by Victor Block
Many a house bears a plaque dating to the 1800’s. Old Town, the largest historic district in the country of predominantly woodedn houses, features almost 3,000 such structures, and it seems deserving of a truth-in-advertising award. There’s a sign near Duval Street, Old Town's town’s epicenter, which reads: “On this site in 1897, nothing happened.” That’s probably one of the only spots in Key West where that’s true.
Renovated cigar factories share streets with Victorian mansions laced with gingerbread trimming (a number of them converted into upscale guest houses), and fancy art galleries reside next to tacky t-shirt shops. Fashion, funk and frivolity define the town; art and schlock and whimsy co-exist on the same bar stool. And yes, those stools are there in abundance – 117 bars on Duval alone, pre-pandemic -- many of which claim that Ernest Hemingway, Key West's most famous resident, occupied that seat as well.
Hemingway House is also famous for its resident cats - with six toes instead of five. Photo courtesy of Key West Visitors Bureau
And Hemingway's home is one of the most visited sites in the city. The tiny second-story studio in the building behind it, in which he wrote a number his prestigious novels, remains exactly as he left it; photos, books and furnishings recall his life there of more than a decade in the 1930’s. Stuffed heads of animals he shot on safari adorn the walls.
You can almost feel the presence of the quirky and fairly disturbed author everywhere. Almost as famous as Hemingway himself was his beloved cat six-toed Snowball, dozens of whose descendants still roam freely here.
Harry Truman often hosted poker games at his winter White House. Photo by Victor Block
Over the years, Key West has been home not just to artists and writers like Hemingway, but also politicians and adventurers. The most notable political figure was the 33rd U.S. president Harry S Truman, who spent part of his winters at the so-called Little White House on the grounds of the local naval base. This two-story affair has its own colorful history, with tales of lively poker games and loud Hawaiian shirt contests with staff and guests from locals to SCOTUS justices. Four other presidents visited here as well.
It’s also rumored that Truman insisted on downing an early morning “shot of bourbon followed by a large glass of fresh-squeezed Florida orange juice,” allegedly on the advice of his doctor. Hemingway, an ardent imbiber himself, would most certainly have approved of his neighbor’s breakfast ritual, which might have made both welcome visitors at Schooner Wharf, which boasts the earliest happy hour in town, beginning at 7:30 am. The theory being that you can’t actually drink all day if you don’t start early.
If Hemingway hunted big game and Truman hunted humor; another Key Wester, Mel Fisher, became famous in the 20th century as a hunter of treasure - as in more than 40 tons of gold, silver, precious gems such as emeralds, Chinese porcelain and other artifacts estimated to be worth $450 million - from Spanish galleons which sank off the Keys in the 17th century. And the Mel Fisher Maritime Museum is packed with loot and copious multimedia exhibits for the visiting public.
Tennessee Williams’ home; photo courtesy of Key West Visitors Bureau
So yes, these are the three attractions for which Key West is most famous, but peeling back the proverbial onion proffers many more enticing sites: the always enchanting Botanical Gardens; the Oldest House with its original furnishings, artifacts and island history dating back to 1829 (see above); and the small cottage of legendary playwright Tennessee Williams (above), though it's privately owned and not open to visitors.
But perhaps my favorite is the Shipwreck Treasure Museum (above), an entertaining (even slightly Disneyesque) presentation of the lives wreckers – who were either brave souls who saved people and ships foudering on the dangerous reefs surrounding the island or greedy pirates who pillaged the lost treasures, depending upon your perspective. In any case, they played an important part in local vibrant history, as the resulting salvage industry is what Key West is built on, making it for a time in the 19th century the richest city per capita in the United States.
On the dining front, there are many options from basic to fancy, and at all price points. But be sure to stop at Blue Heaven, centered around a rustic yard where in the 1930’s amateur boxing aficionado Hemingway refereed matches (and back in the day also housed a dance hall and bordello). Today diners enjoy tasty fare inside or more typical out in the yard, shared with - yes, roosters. But you’d expect nothing less of Key West, right?
T-shirt shops share space with more elegant stores on Duval Street in Key West, Florida Photo by Victor Block
And of course Old Town Key West's main drag Duval Street is one of the USA's most entertaining, lined with bars, restaurants, and shops - some tasteful, others monumentally tacky (lower Duval in particular, which tends to cater more to the cruise-ship crowd which descends in the thousands many days during the sailing season. For me, the best way to experience the inimitably funky charm of the town is to just wander Duval and other streets, laughing your way from one t-shirt slogan to another, most of which can’t be repeated in a family blog. But some that can include: “A good lawyer knows the law; a great lawyer knows the judge”; “4 out of 3 people struggle with math”; and “Mermaids smoke sea weed.” Bada boom!
In short, Key West promises everything in excess, including history, adventure, music, shops, and nightlife. And what it offers most of all is fun - and also roosters.
For more information, check out fla-keys.com/keywest.