By Gary Bennett
They say Key West is for pirates, parrots and poets. I didn’t see any of those on a recent visit, but the phrase captures the island’s whimsical, creative and laid-back spirit. Like Las Vegas or New Orleans, it’s one of those places every American should experience at least once before they head off to that great overseas highway in the sky.
And speaking of highways, few routes are as memorable as the 113-mile Florida Keys Overseas Highway. Stretching from Key Largo to Key West across an astonishing 42 bridges, it hopscotches from island to island, each with its own personality. The drive delivers uninterrupted ocean views, glimpses of coral reefs, dolphins and endless boat traffic. Think dozens of Chesapeake Bay Bridges lined up end to end.
Yes, Key West has its own international airport with flights from across the U.S. and abroad, but I’m not sure why anyone uses it. Flying into Miami, renting a car, and driving the Keys offers a breezy, scenic adventure filled with quirky shops and water in every direction. It goes by quickly.
Key West is the southernmost city in the continental U.S. Surprisingly, it’s closer to Havana (90 miles) than to Miami (165 miles). Jutting far into the Atlantic Ocean and Gulf of Mexico, the island has a tropical climate and is regularly hit by hurricanes and tropical storms.
With weather similar to a Caribbean island, daytime and nighttime temperatures rarely vary by more than 15 degrees at any time of year. Prevailing easterly trade winds keep summer temperatures from climbing too high and winter temperatures from dropping too low. It’s rare for the thermometer to reach 95 degrees.
As you pull into town, you’ll notice palm-shaded streets, stately historic homes, salty air and nightly waterfront sunsets that are astonishingly beautiful. Only about 30,000 people live here full-time. Because the weather barely shifts from season to season, visitors come throughout the year, which helps disperse crowds. We’ve visited in both January and August; the weather felt almost identical, and the island never seemed like an overwhelming tourist trap — more like a homey escape.
Many early residents immigrated from the Bahamas and were known as “Conchs” (pronounced “conks”). In the 20th century, residents began embracing the term, and today it generally refers to full-time locals.
One of the island’s most beloved stories dates to 1982, when Key West symbolically declared independence as the “Conch Republic” in response to a U.S. Border Patrol blockade at the junction of U.S. Route 1 and the mainland. The blockade created major traffic delays and disrupted daily life. Although the secession was purely symbolic, the tale endures, and the Conch Republic Independence Celebration is marked annually on April 23.
Key West is compact in both population and size, but you’ll want at least three or four days to get a real feel for the place.
MUST-SEES
Start with a visit to the southernmost point in the continental U.S., marked by a giant, whimsically painted concrete buoy. Locals say the point was once indicated by a simple sign, but constant photo-seekers led to its upgrade. Here you’ll also find the “90 miles to Cuba” marking. It’s kitschy, but worth the photo (this is one of the most photographed spots in the country). The marker sits at 1400 Whitehead Street on the waterfront, and there’s no admission fee. When we visited, the line was short and we snapped our picture in minutes.
Next, grab a photo at Mile Marker 0, the literal and figurative end of the road in America. It marks the southern terminus of U.S. Route 1, the longest north-south road in the nation. For the dedicated road-tripper, its northern end is in Fort Kent, Maine, near the Canadian border. Driving it straight through would take more than 50 hours — and you’d likely hit every stoplight in every small town along the way.
Take a leisurely walk down Key West’s most iconic street, Duval Street, the island’s historical, entertainment, culinary and cultural center. It runs 14 blocks — about a mile — from the Gulf of Mexico to the Atlantic Ocean. No one rushes here; you’re on island time.
Under the category of “only in Key West,” don’t be surprised if free-roaming chickens wander across your path. They strut around as if they own the place — and perhaps they do. Early Cuban settlers brought chickens for food and cockfighting. When supermarkets took over and cockfighting was outlawed, many birds were released. Today, locals often prefer the chickens to tourists, and attempts to control their population have sparked strong resistance.
Once you’ve navigated the chickens, visit two historic landmarks: the Ernest Hemingway Home and the Harry S. Truman Little White House.
Hemingway lived in Key West from 1931 to 1939. His wife’s wealthy uncle purchased the home as a wedding gift. It features an impressive swimming pool that cost the equivalent of nearly $350,000 today. Here, Hemingway was introduced to deep-sea fishing by Joe Russell (the original “Sloppy Joe”) and acquired his lifelong nickname, “Papa.”
These were his most productive years. He wrote “For Whom the Bell Tolls,” “The Snows of Kilimanjaro,” “To Have and Have Not” and “Death in the Afternoon” in the mornings at his estate, reserving afternoons for his family. (“A Farewell to Arms” was completed before he arrived in Key West.)
President Harry S. Truman visited Key West 11 times during his presidency, spending a total of 175 days there, mostly during winter. At the Little White House, he conducted official business and worked on the Truman Doctrine, which pledged political, military and economic support to democratic nations threatened by authoritarian regimes. President Dwight Eisenhower later recuperated there after a heart attack, and Presidents John F. Kennedy and Jimmy Carter were also frequent visitors.
While in town, stop for a drink and a meal at Sloppy Joe’s Bar. The food and drinks themselves are nothing remarkable, but the history is. Founder Joe Russell, a rumrunner from Cuba, needed a place to sell his goods. With encouragement from Hemingway, he opened The Blind Pig, which became Hemingway’s favorite bar. Hemingway suggested renaming it “Sloppy Joe’s” in reference to the wet floors caused by melting ice used to sell seafood. The name stuck.
In one legendary episode, Russell — unhappy paying $4 a month in rent during the 1930s — moved the bar down the block, “lock, stock and barrel,” with help from his customers, who continued drinking as they carried furniture and supplies. The landlord was furious but could do little about it.
End your stay with the sunset celebration at Mallory Square, held nearly every night of the year. This waterfront event begins an hour before sunset and features artists, craftspeople, psychics, street performers, food vendors and crowds of locals and visitors who gather to watch the sun sink into the Gulf to cheers and live music.
Gary Bennett is a longtime Frederick resident who spends his time hiking, biking, volunteering and providing childcare for grandchildren. He is married and retired from his career as a nonprofit marketing executive.