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At the southernmost tip of the Florida Keys archipelago where the Gulf of Mexico meets the Atlantic Ocean lies Key West, once a crucial military outpost and now a popular boating and tourist destination recognized for its quirky denizens and laid-back vibes. For the past 10 years, yours truly has joined the flotilla of boaters and snowbirds who escape to this unique island when things get chilly on the mainland. During my time, I’ve come to appreciate its rich history, which virtually oozes from its pores, so much so that a single article could never capture it all. It’s in this vein that I’d like to share a few of my favorite places with Marinalife readers making plans to visit Key West.
First, a word about the name Key West. The 16th century Spanish settlers originally called the island “Cayo Hueso,” which translates to “Bone Island,” referring to the scattered bones of the Calusa Indians who once lived in the Keys and perhaps also as a nod to the white coral rock on the beaches that resembled bleached bones. English speakers later anglicized it to Key West and the name stuck.
Key West is also known as the Conch Republic due to a symbolic secession in 1982. That year, the U.S. Border Patrol set up a drug smuggling blockade on Route 1, the only road connecting Florida Keys to the mainland. It caused significant inconvenience and economic hardship for Keys residents and businesses.
In response, Key West declared its independence. The humorous stunt gained significant attention and helped get the roadblock removed. Since then, the Conch Republic has become a part of local identity and culture, celebrated with an annual independence festival in April.
You can’t visit Key West without bumping into the celebrated author Ernest Hemingway. Not literally, of course, because he’s dead, but his presence permeates the place. In fact, the most popular historic site in Key West is the house where he lived in the 1930s and sporadically through the 1940s. Built of native limestone, the two-story Spanish Colonial style home is filled with Hemingway memorabilia, photos, books and furniture.
While you can roam the house and gardens solo, I’d suggest joining a tour because the guides are incredibly knowl - edgeable and entertaining. For example, I learned the 60-foot saltwater swimming pool was once the largest in Florida. Hemingway’s second wife Pauline commissioned it when she found out he was having an affair with a journalist while overseas reporting on the Spanish Civil War. For spite, she had it built on the site where Hemingway liked to host neighborhood boxing matches.
Then there are the cats. Hemingway loved pussies and according to one guide the dozens of polydactyl (6-toed) cats roaming the house and grounds today are descendants of a cat named Snow White, given to Hemingway by a local ship captain. It’s said Hemingway fed his felines fresh fish and added whiskey to their milk. Knowing the writer’s affinity for drink, I’m not surprised.
The striking, four-story red brick building beside Key West harbor was built in 1891 and served as the city’s original customs building, post office and courthouse. A national landmark, it now features permanent and changing exhibitions weaving together Key West’s 200+ years of history, art, people and events.
The permanent exhibit with photos and a film about oil tycoon Henry Flagler and his unwavering obsession to erect an overseas railroad linking Key West to the mainland is a must see. But don’t overlook the small room showcasing the work of artists who came to Key West with the Depression Era Works Progress Administration (WPA) program. These artists were part of a plan to promote the city as a vacation paradise, though I’m not sure all their work hit the mark.
The museum also houses the largest known collection of paintings by Tennessee Williams, another celebrated author who made Key West his home from 1949 until his death in 1983.
Key West is a drinking town, and one of its oldest watering holes is the Green Parrot Bar. Once a hangout for WWII submarine sailors stationed at the Key West Naval Base, the bar today is funky, open air and laid back with a free-spirited clientele and great live music.
There’s a pool table, dart board and so many odd paintings and local artifacts that the bar has been called Key West’s attic. Plus, it’s not as popular with the cruise boat crowd as some other well-known bars. In a town that’s always changing, the Green Parrot is one venue that seemingly remains the same, and the locals who frequent it like it that way.
The wooden-frame house that is now the La Te Da hotel, restaurant and bar was constructed in 1892 by Teodoro Perez, the island’s premier cigar manufacturer and a well-known supporter of the Cuban independence movement. As soon as his house was finished, he invited his friend José Martí, the poet and head of the Cuba Revolutionary Party, to visit and drum up money for weapons and ammunition.
As the closest port to Havana, Key West was a hotbed of anti-Spanish sentiment around the turn of the century. During his stay, Martí gave speeches from the second-floor balcony overlooking Duval Street. Local Cubans soon began referring to Perez’s house as “La Terraza de Martí” or “the Balcony of Martí.” The restaurant is top shelf, and the open-air terrace bar is a perfect venue for people watching and listening to live entertain- ment from the adjacent piano bar. The martinis are pretty darn good, too.
Key West cemetery is a lot like the city itself: quirky, crowded and a tad unkept. It was founded in 1847, and the graves reflect the long history and diversity of Key West and range from simple markers to obelisks and elaborate mausoleums. The cemetery has Jewish and Catholic sections, an area for Cuban martyrs, and plots for priests.
The most prominent monument is to the USS Maine, which was blown up in Havana Harbor in 1898 killing 260 American sailors. Two dozen of those dead are buried here along with other veterans of the Spanish-American War.
Stroll about and you’ll undoubtedly notice the photogenic wild chickens and iguanas that frequent the grounds. But don’t let them distract you from the epitaphs on the graves. A few will make you laugh. On one grave: I Told You I Was Sick. On another: I Always Dreamed of Owning a Small Place in Key West. FYI, the small cemetery office offers an excellent free walking tour guide.
During the Civil War, Key West remained in Union hands thanks to several federal forts in its vicinity. Constructed in 1862, Fort East Martello today serves as a historical museum (it was the first in the Florida Keys) and a small art gallery. Visitors can explore the preserved battlement’s collection of relics from the Civil War, learn about Key West’s wrecking and cigar manufacturing industries, as well as meet the infamous Robert the Doll.
Once a local child’s plaything, Robert the Doll is Key West’s creepiest and most famous haunted spirit, often accused of tragedies that befall those who disrespect him. According to the museum curator, Robert casts curses on those who take his photo without first asking permission.
Now 117 years old, Robert resides in a glass display case with humidity control and UV-filtered glass and surrounded by letters from previous visitors and naysayers begging Robert’s forgiveness and asking him to remove any hex he has cast.
I took a photo of the pockmarked straw-filled doll two years ago before I knew the backstory and since have had foot surgery, pink eye, and a strange case of beard psoriasis. Perhaps I’ll hand deliver my own letter to Robert this coming winter when I head back to the eccentric little island.
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