You might not think that roosters, six-toed cats, Hemmingway and President Truman share anything in common. But they do, having each called Key West home at one point or another. And some, like the roosters and cats, have become permanent denizens of this irreverent southernmost, subtropical paradise.
Located closer to Cuba than to Miami, this Florida destination is known for its colorful history, sunny, warm climate, natural beauty, cultural diversity and unique architecture. The streets are lined with palm trees and you’ll see conch homes with tin roofs aside gingerbread mansions. There’s a romantic appeal about this place that’s undeniable.
Hemmingway, along with numerous other notables like Robert Frost, Tennessee Williams and yes, Jimmy Buffet, found inspiration in this island city with its Bahamian and Cuban heritage. They, like so many, discovered a community of acceptance and freedom to embrace their identities.
As for the roosters, they have roamed Key West since the 1800s when Cubans and Bahamians brought them over for cockfighting. When the sport was outlawed in the 190s, the creatures, left to their own devices, multiplied. Today, they can be found everywhere and you can’t miss hearing them crow at all hours of the day and night. They truly rule the roost and have become an unofficial mascot for the town. And don’t even think of feeding them or harassing them. If caught, you’ll face a $500 fine.
The story behind the cats relates to Ernest Hemingway. The famed writer was given a white six-toed kitten, Snow White, by a ship’s captain back in the 1930s. Sailors favored these polydactyl cats, believing they were good luck. Supposedly, their extra toes gave them better abilities as mousers on the ships, while helping them maintain better balance on rough seas.
One cat led to another and today many descendants of Snow White live on the museum grounds of the Hemingway Home and Museum, with about half of the sixty odd resident cats exhibiting the physical indicator of extra toes.
Hemingway named all of his cats after famous people, like Betty Grable, Joe Di Maggio, Clark Gable and Hunter S. Thompson, and the keepers of his home have continued that tradition. When you visit the house, you’ll find these felines everywhere, on Hemingway’s custom-made bed, sunning themselves on the veranda, sleeking along the walkways, ensconced in the stairwells…And don’t miss the Cat Cemetery, where there are miniature gravestones commemorating the lives of these celebs.
You’ll hear all about Papa Hemingway when you tour this beautiful Spanish colonial home with lush gardens. Guides regale visitors with stories of the author’s over-the-top machismo, his feuds with other writers, the amount of alcohol he consumed nightly, the fistfights he had with other inebriated souls, his fishing conquests and more. There are photos galore, movie posters and an assortment of artifacts and Hemingway’s belongings.
On the grounds, you’ll also find Hemingway’s bungalow, where surrounded by animal heads and stuffed fish, he wrote each day, in longhand, at least five hundred words, hung-over or not. There’s a swimming pool, too – the first in-ground pool on Key West, which was exorbitantly expensive for its time. Story has it that Pauline, Hemingway’s second wife, tore down his boxing ring and had the pool built while he was away. When he returned, he became so angry with what she had done that he took a penny from his pocket and tossed it down, saying, “You have succeeded in spending my last red cent!” She promptly had it embedded in the pool patio.
For the Truman connection to Key West, you’ll need to visit Truman’s Little White House. Take a tour of what was once the winter White House for this President and see where he lived, worked, played and held important government meetings.
Over the years, numerous dignitaries made use of the Little White House, including Presidents Taft, Kennedy, Carter and Clinton, and even the inventor Edison, who stayed for six months while formulating new weapons for the war efforts.
There are many other people who have had significant impact on the island and you can find them at the Key West Historic Memorial Sculpture Garden. Within this oasis are impressively cast bronze busts of thirty-six influential residents, with information about their contributions.
When you’re not learning about all the famous inhabitants of Key West, you can enjoy a wide variety of watersports, charter a boat for some deep-sea fishing, go shrimping, shop till you drop, take in a musical or theatrical show on local stages, catch some rays on the beach and stroll along the busy, historic harbor front or peaceful back streets, as you ooh and ahh at the floral bounty bedecking the homes and gardens.
I guarantee you’ll be taking pic after pic during your amblings around town, as this is one very photographic destination. Among the many sought-after sights that tourists want to capture on their phones and cameras is the Southernmost Point Buoy. Preferably, they want a photo of themselves in front of this landmark. Like the name suggests, the buoy does mark this geographic point in the continental U.S. – almost. Technically, the exact place is Ballast Key, but the public can’t go there. And really, who’s worried about a technicality? When you see a long line of patiently waiting folks, you’ll know you’re in the right place. My advice, go early to have the spot to yourself.
Food also has a starring role in Key West, with restaurants for every palette and budget. To get a good overview of the local cuisine, I recommend taking a tour with Key West Food Tours. The “Southernmost Food Tasting and Cultural Walking Tour” is one of the company’s most popular offerings. It celebrates the Cuban and Caribbean influences on both food and culture in the Keys.
You’ll stop at five, locally-owned establishments for hearty tastings and along the way, your guide will provide insights about the city’s history, culture and architecture, plus give tips on where to visit and eat during your trip.
Our tour started at El Siboney, a longtime, family-owned and operated restaurant, specializing in authentic Cuban food, paella and local seafood. We sampled some delicious Puerco Asado, marinated roasted pork, with white rice, black beans, plantains and Cuban bread.
Next stop was The Speakeasy Inn and The Rum Bar for a Rum Runner cocktail. This establishment is located in an historic building with two unusual features. The first are the balustrades around the second-floor balcony, which depict shapes of bottles, hearts and spades. Homeowner Raul Vasquez brought these back from Cuba so he could advertise the fact that there was alcohol and gambling available during Prohibition times. He smuggled the rum back from Cuba, too, and stored it in his basement (unusual feature number two). Basements are few and far between on the island, as there’s just too much water underground to make basement construction practical or feasible in most cases.
This snug watering hole offers 350 plus rums from around the world. If you want to try a few, ask for a flight. The bartenders here are knowledgeable and always happy to give you information about the different rums. They can make just about any drink you want, but, as you might expect, traditional tropical rum drinks are their forte. The house specialty is a Painkiller and I’m told this libation is legendary on the island.
At Mangoes, we had freshly made conch fritters with Key Lime aioli. Our guide talked to us about conch (pronounced “konk”), a mollusk similar to calamari in texture. It’s readily available on the island and very versatile. Many restaurants serve conch dishes and you’ll find conch salad, conch chowder, cracked conch burgers, conch wrapped in tortillas, breaded and deep-fried.
Our guide told us that people born and raised on Key West are called “conchs,” while those who live here but are born elsewhere are known as “fresh-water conchs.”
She then shared why Key West is called the “Conch Republic.” It all started in March of 1982 as a response to a roadblock on the main highway between the Keys and mainland Florida. The Border Patrol erected this blockade to stop vehicles and search for drugs and illegal immigrants. It created a massive traffic jam and was a major pain for residents in the area. To comprehend how serious this was, you need to know there are only two roads that connect the mainland to the Keys.
City council members tried to stop the roadblocks and searches by complaining to the federal government and attempting to get injunctions against the action. But they failed. In protest, Mayor Dennis Wardlow, declared the independence of Key West on April 23rd of the same year. He reasoned that the roadblocks acted as a border station, which meant that the government was treating the Keys like a foreign nation. So, in his mind, they might as well act like one.
Wardlow was designated the Prime Minister and the territory became the Conch Republic. There was much hoopla generated over this tongue-in-cheek secession, but the publicity had an effect. It didn’t take long before the roadblocks were removed, however, the Conch Republic remained. You can actually still get a Conch Republic passport, driver’s license and identification card. And if you fly in to Key West, you’ll see the “Welcome to the Conch Republic” sign at the airport.
Back to the food tour and to Kaya Island Eats for some delicious mahi mahi with pineapple salsa and coconut rice, perhaps my favorite of the samples on the tour. The flavors melded so well and I know if I have this dish anywhere else in the future, it will take me back to Key West in a visceral way.
Last stop was Cuban Coffee Queen to sample real Cuban coffee – strong, oh, so strong! And to accompany it, a slice of perfectly tart Key Lime Pie. I’m besotted with anything that has Key Lime in it and love that you can find it in everything from ice cream and sauces….to lotions and potions.
As the sun sets, the nightlife on Key West gets going in a big way. People flock to the bars and restaurants to eat, imbibe and party hearty. Live music and entertainment overflows onto the main streets and all along the harbor front, and the crowds get more raucous by the hour. It’s a great people-watching scene!
Those who are staying in one of the hotels or inns that are centrally located to all the action have a better chance of finding their way back to their rooms late at night without too much issue, stumbling aside. Or you can be like Hemmingway, who used the island’s lighthouse to navigate home after a night of debauchery.
If your lodging is in the heart of town, you only have to park your car once, as most everything is walkable. During my time on the island, I stayed at The Marker Key West, a luxury, amenity-rich, boutique property set on two beautifully landscaped acres, featuring 96 rooms and suites, three swimming pools (one is adult-only) and an onsite restaurant and bar. This special haven has the feel of a tropical island resort escape, yet it’s situated right on the Historic Seaport and close to restaurants and attractions.
Rooms are spacious and airy, with lots of natural light, while the décor is fresh and breezy. Private balconies offer various views; some overlook the pools, others gaze out at the harbor, where you can be dazzled by a fiery sunset or watch the parade of boats pass by.
Beds are super comfy with sumptuous linens. Bathrooms feature soaking tubs and walk-in rain showers, with Key West Aloe bath products (my new favorites!). And if you are one of those who needs to exercise in a gym, no worries, as there’s a state-of-the-art fitness center where you can do some heart-pumping cardio or weight training.
Rent bikes, book a boat trip or watersport activity, get directions and restaurant suggestions, reserve show tickets…ask and you shall receive, as the concierge here is a font of knowledge about all things Key West.
If you go: