Things to Do in Key West: Island End of the Road
There is a moment when you cross the last of the bridges from the mainland and the road finally runs out at the southernmost point of the United States. Key West greets you with a swagger all its own, a blend of conch culture, pastel houses, fishing history, and an easy going rhythm that is hard to shake even after you leave. I spent a long weekend here and packed in as much as I could. Here is how I did it, in the order I would recommend.
Watch the Sunset From Mallory Square
Every evening the whole island seems to migrate to Mallory Square for the sunset, and I now understand why. The old pier fills with jugglers, tightrope walkers, and musicians performing against the wide open horizon, while boats drift past and the sky turns orange then pink then deep purple over the Gulf. I got there early to claim a spot on the railing and watched the entire performance build to the moment the sun slipped below the water, when the crowd actually applauds. It is touristy, sure, but the energy is infectious, and I never missed it once in my three nights.
Walk Duval Street and the Little Neighbourhoods
Duval Street runs from one end of the island to the other and is the spine of Key West life. In the day it is full of shops, galleries, and houses with wide wraparound porches dripping with bougainvillea. At night the bars take over, and I wandered the blocks listening to different live bands spill out of every doorway. The real joy, though, is stepping off the main drag into the quiet side streets, where the gingerbread cottages and garden lanes give you a calmer picture of island life between the noise.
Visit Ernest Hemingway’s House and the Famous Cats
The writing room where Hemingway worked sits in a walled garden in the middle of town, and the house is now a museum faithful to the period. I walked through the rooms he lived in, saw his studio above the pool, and met some of the six toed cats that roam the grounds, descendants of his famous pets. The garden itself is lush and shady, perfect for cooling off between stops. Even if you have never read his books, the history and the house’s character make it worth the entry fee.
Climb to the Top of the Lighthouse
Next door to the Hemingway house, the Key West Lighthouse gives you the best view over the treeline rooftops of the old town. I climbed the spiral staircase to the top and looked out over white wooden houses, palm trees, and the sea on three sides. It is a short, easy climb and the payoff is immediate, and because the crowds tend to skip it, I found myself alone up there for a while. Turn it into a morning stop with the Hemingway house and you have a perfect historic duo.
Take a Big Day on the Water
The water is the heart of the Keys, and no trip is complete without a proper day of it. I joined a catamaran sail out to the reef, where I snorkelled over living corals and schools of fish in water so clear it looked staged. On the way back the crew hooked a line and we watched dolphins playing in the wake. For something even more memorable, some operators offer a longer crossing to the remote sand flats where you can wade in waist deep turquoise water for hours. Either choice beats staying ashore.
Eat the Conch Specialties and Seafood Everywhere
Key West has its own food culture built on the sea. I ate conch fritters, golden fried balls served with a spicy dip, and I tried conch in a ceviche that tasted of pure lime and ocean. For bigger meals I worked my way through the catch of the day, grouper, snapper, and shrimp, in a string of low key restaurants and dockside shacks. Breakfast was easy, too, with plenty of spots serving eggs benedict and strong coffee on shaded porches. I made a rule of never ordering anything I could not find fresh on the island.
Race to the Southernmost Point and Save Room for the Keys Beyond
The famous painted buoy marking the southernmost point of the continental US draws long photo queues, so I went at first light when it was quiet. After your fill of the old town, one more joy of Key West is that the rest of the Keys string out behind you. I hired a bike and rode a stretch of the flat route along the water, and I also took a short drive back toward the big islands for the long bridges and the fishing villages. Whether you stay put or push on, Key West leaves you with that rare, sun soaked ease, and I spent my whole trip back on the mainland wanting more.
