Exploring Another World in Key West

March 26, 2021 Updated: March 26, 2021

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.”

The sun sets out over the Gulf of Mexico, as seen from Key West. (Ricardo Reitmeyer/Shutterstock)

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?

Old Town Trolley tours provide engaging, narrated history of Key West. (GagliardiPhotography/Shutterstock)

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.

The Ernest Hemingway Home & Museum. (KAREN BLEIER/AFP via Getty Images)

How to Get There

Key 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.

One of the six-toed cats of the Ernest Hemingway Home and Museum on Aug. 30, 2020. (LEILA MACOR/AFP via Getty Images)

Getting to Key West can be a bit tricky; one option is to fly into Miami International Airport, which has a lot of flight options, and from there you can rent a car, book a seat on the Keys Shuttle, or even book an hour-long connecting flight to get to Key West. Another option is to fly directly into Key West International Airport, though flight options are limited and tend to be pricey. Many people arrive via cruise ship, at least in normal times.

Key West Faces Tough Economic Road As Coronavirus Closures Affect Tourism
Roosters on Duval Street. (Joe Raedle/Getty Images)

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.

Tourists look out over Key West, Florida
Tourists look out over Key West from the top of the Key West lighthouse in this file photo. (KAREN BLEIER/AFP via Getty Images)

History, Sunsets, and Food With Character

A 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.

Ernest Hemingway Home in Key West
Denny Woods, who won the 2001 Ernest Hemingway contest, visits the home/studio where the real Hemingway wrote many of his classic books, on July 22, 2001. The home is where Hemingway wrote classics such as “Death in the Afternoon” and “For Whom the Bell Tolls,” among others. (Joe Raedle/Getty Images)

Most visitors will spend most of their time on land; luckily, there’s plenty to do. Any city where Old Town Trolley Tours are available, I’m going to recommend taking one, and Key West is no exception. In fact, it’s one of my favorite cities for this tour because there’s just so much funky history you’d miss out on otherwise—and Key West loves its tourists, so the tour guides tend to be especially informative, interactive, and engaging.

A sign welcomes visitors to Mallory Square. (Luiz Barrionuevo/Shutterstock)

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.

Visitors gather on colorful bar stools lining Sunset Pier at Mallory Square in Jan. 2019. (lazyllama/Shutterstock)

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).

Kermit’s is one of the places to taste key lime pie. (LMspencer/Shutterstock)

While you have Hemingway on the brain, head over to one of his favorite haunts, now a Key West institution: Sloppy Joe’s Bar. You practically haven’t visited Key West unless you made a stop at Sloppy Joe’s, so pop in for an original Sloppy Joe sandwich and a dose of history: the bar opened, conveniently, the very day Prohibition was repealed in 1933. It’s been a Key West staple ever since.

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.

Sloppy Joe’s Bar opened on Dec. 5, 1933, the day Prohibition was repealed. (Fotoluminate LLC/Shutterstock)
sloppy joe's bar
Sloppy Joe’s Bar opened Dec. 5, 1933, on the day Prohibition was repealed. (Courtesy of Sloppy Joe’s Bar)
sloppy joe and white claw
A sloppy joe at Sloppy Joe’s. (Courtesy of Sloppy Joe’s Bar)

There’s a lot to explore in Key West, so if you start feeling drowsy, it’s best to grab a cortadito from Cuban Coffee Queen to perk you right up. This charming coffee stand, which is painted with the iconic “Greetings from Key West” mural on one side, is representative of Key West’s Cuban heritage; it’s only 90 miles to Cuba from the southernmost point (where all tourists stop to snap a photo), and Cuban refugees have been settling here since the 1830s.

cuban coffee queen
Lining up for cafe con leche at Cuban Coffee Queen. (Courtesy of Cuban Coffee Queen)
cuban coffee queen
A spread of sandwiches from Cuban Coffee Queen. (Courtesy of Cuban Coffee Queen)

Another Key West must? Tasting several different versions of its famous key lime pie. Organize your own tasting tour, sampling the town’s many different takes on this sweet-tart concoction. At Blue Heaven, you’ll find a version with a tall tower of meringue, while at Kermit’s (and many other spots around Key West), it’s key lime pie on a stick: it’s a frozen slice dipped in Belgian chocolate and put on a stick, which makes it (somewhat) easy to walk and eat on the go. Rich and unique, it’s the spirit of Key West captured in one memorable bite.

Skye Sherman is a freelance travel writer based in West Palm Beach, Fla. She covers news, transit, and international destinations for a variety of outlets. You can follow her adventures on Instagram and Twitter @skyesherman