If there’s anywhere in the continental United States that’s a true getaway from reality, it’s Key West. One of the funkiest towns in the country, this small tropical island—the last in the Florida Keys archipelago—follows the beat of its own drum, to say the least.
In fact, Key West proved its fierce independence by declaring itself the Conch Republic with a tongue-in-cheek “secession” in 1982. The flag of the Conch Republic, which you’ll see flying from many a front porch in Key West, jokingly declares “We Seceded Where Others Failed!” and its proud citizens live by the motto: “We’re all here because we’re not all there.”
Visit today and you’ll agree that Key West is a town that plays by its own rules—and has a whole lot of fun doing so. It’s a blast to visit, especially during a time when many cooped-up Americans facing restrictions crave the chance to get out, enjoy some sunshine, and let their hair down. What better place to do so than America’s own piece of paradise, a spot as blissfully tropical as any (currently-hard-to-get-to) Caribbean island, no passport required?
While Key West does have virus-prevention safety protocols in place, Florida remains one of the most famously lax states in the country, in part due to year-round mild weather and the resulting ability to soak up the great outdoors no matter the month. In recent months, people—especially freshly vaccinated seniors—have taken notice. Key West has seen high numbers of tourists this winter and spring, with many weekends fully sold out in hotels across town.
How to Get ThereKey West sits at mile marker zero. In other words, it’s pretty far from the mainland—128 miles and 42 bridges, to be exact. As the southernmost point in the continental United States, it’s at the very southern tip of the Florida Keys island chain, which extends off the southeast tip of the Florida peninsula.
Once in Key West, you can rent a car or get around via bicycle, ridesharing, or even your own two feet, especially if you stay near one of the main drags like Duval Street or Mallory Square. Key West isn’t very big—about four miles long and two miles wide—and the popular Old Town makes up about half of this area, but you will likely want to be able to explore further than your own feet can carry you, so renting a bicycle can be a great option during your stay.
History, Sunsets, and Food With CharacterA common misconception about Key West (and the Florida Keys as a whole) is that because it’s a tropical destination, there must be beaches, but this is, oddly, inaccurate. Key West isn't a beach town and there really aren’t many sandy shores; instead, people go there to enjoy the history, culture, and town. If you do want to get out on the water during your visit, it will be via sailing, snorkeling, diving, or boating excursions.
Taking an open-air trolley tour is a great activity to do on your first day to both get the lay of the land and cover a ton of ground, which can help you find places you want to circle back to. Your ticket includes unlimited hop-on and hop-off all day long, so you can disembark where you please and get transported all around the island.
You’ll hear Key West’s history on your tour, but before you go, you should know that this spot has long attracted artists, poets, and creative types—including, famously, Ernest Hemingway and his beloved six-toed cats. Touring the Ernest Hemingway Home & Museum is a must on any visit to Key West.
Approximately 60 quirky-looking cats roam the property freely, many of them likely descendants from Hemingway’s own original cat, Snow White, whom he received as a gift from a ship captain (sailors preferred polydactyl cats, believing their extra toes made them exceptionally deft mouse-catchers).
Like many popular bars and restaurants in Key West, Sloppy Joe’s is located on Duval Street, one of the main drags to shop and stroll. Stick around here to find things to do during the day, but come time for sunset, head over to Mallory Square, located on the street’s northern terminus. Sunset is celebrated every night on Mallory Square with street performers, artists, and eccentrics. It offers a splendid view of the setting sun, which usually appears in brilliant reds, oranges, and yellows, made especially beautiful as it reflects over the tropical blue waters.