Key West sits at the end of a 180-kilometre chain of coral islands linked by the Overseas Highway — the southernmost city in the continental United States, 145 kilometres from Cuba, with a character that reflects its isolation, its history as a Navy town, its fishing culture, and its long tradition as a refuge for writers, drinkers, and people who didn’t fit particularly well anywhere else. Ernest Hemingway lived here for most of the 1930s. Tennessee Williams spent his winters here. The sunsets over the Gulf are a civic institution.
We took a road trip down to Key West. It’s a long way down and takes a surprising amount of time to get there. The journey is perhaps more interesting than the destination. We found Key West to be expensive, not really a beach destination and probably great if you’re fond of boating and fishing. Getting to and from Key West is very picturesque providing you can find places to stop and take photos!
A Little Background
The Calusa people inhabited the Keys before European contact. The island was known to Spanish sailors as Cayo Hueso (Bone Key) — possibly for the bones of the Calusa found here, or possibly a mis-hearing of a name that has been lost. American control came with the purchase of Florida in 1821. The Navy established a base here in 1823, and Key West became one of the wealthiest cities per capita in the United States in the mid-nineteenth century, its prosperity based on wrecking (the salvage of ships that ran aground on the reef) and sponging.
The wrecking industry collapsed when lighthouses made the reef navigable; the cigar industry flourished briefly; the sponge industry collapsed when a blight hit the sponge beds in the 1940s. The Navy base, which brought men, money, and infrastructure during both World Wars, was the city’s economic anchor for most of the twentieth century. Tourism came later but now completely dominates the economy. The LGBTQ+ community that settled in Key West from the 1970s onward contributed significantly to the city’s current character and its accommodation of difference.
What to See and Do
The Ernest Hemingway Home and Museum on Whitehead Street is the house where Hemingway wrote For Whom the Bell Tolls, A Farewell to Arms (revised here), and The Snows of Kilimanjaro, among other work. The house is as he left it, more or less, and is populated by approximately fifty polydactyl (six-toed) cats, descended from Hemingway’s original cat. Adult approximately US$16.
The Key West Butterfly and Nature Conservatory on Duval Street is a glass-enclosed garden with hundreds of free-flying tropical butterflies, and considerably more worthwhile than its location on the tourist strip suggests. Adult approximately US$15.
Mallory Square at sunset is the institution — every evening, the town gathers on the waterfront plaza west of the old town to watch the sun go down over the Gulf. Jugglers, acrobats, musicians, and an audience that takes the ritual seriously. Free.
Fort Zachary Taylor Historic State Park is at the island’s western tip — a Civil War-era Union fortress (Key West remained Union during the Civil War, a fact that surprised many Floridians) with the largest collection of American Civil War cannon in the country, and a beach on the Gulf side that is the best swimming beach in Key West, with coral rubble and clear water. Admission approximately US$6 per vehicle.
The Duval Crawl — Duval Street is Key West’s main tourist strip, a kilometre of bars from the Atlantic to the Gulf. It is what it is, and it has a certain commitment to its own excess that commands a grudging respect. Sloppy Joe’s Bar, which Hemingway frequented, has moved from its original location but is still there. The Southernmost Point buoy, at the foot of Whitehead Street, has a permanent queue of people wanting to photograph themselves at 24°33′N.
Snorkelling on the reef — the Florida Reef is the only living coral barrier reef in the continental United States. Glass-bottom boat tours and snorkel charters run daily from the Garrison Bight marina; a half-day snorkel trip costs approximately US$40–55. The reef is approximately 10–15 kilometres offshore.
Getting There
Key West International Airport (EYW) has connections to several Florida cities and a handful of East Coast destinations. Most people arrive by road: the Overseas Highway (US-1) runs the length of the Florida Keys, 180 kilometres from Florida City to Key West, with 42 bridges including the 11-kilometre Seven Mile Bridge — one of the more dramatic road journeys in the United States. Greyhound buses run from Miami. The Florida Keys Overseas Heritage Trail provides a bike path running roughly parallel to US-1 for most of its length.
Cost and Hours
Key West is expensive relative to mainland Florida. Mid-range hotels run US$200–350 per night; higher during Fantasy Fest (late October) and spring break. Off-season (September–November) prices drop significantly. Allow two nights minimum; three is comfortable.