7 Things You Need to Do in Key West

Key West sits approximately 100 miles from the Florida mainland in the western Florida Keys. Across only 4.2 square miles, the island destination offers a range of activities, from picturesque beaches and verdant flora to immersive history and delicious cuisine. 

Whatever you decide to do on Key West, make sure to take a deep breath and relax. Life moves slower here, and, in order to enjoy your vacation, so should you. Ready to decompress? Here are seven things you shouldn’t miss on your trip to Key West. 

Delve into History 

A number of notable historical figures have called Key West home. Among the most famous are the writers Tennessee Williams and Ernest Hemingway, the latter of whom lived in the Spanish colonial mansion that’s now known as the Ernest Hemingway Home and Museum. Take a tour of the residence where Hemingway penned parts of For Whom the Bell Tolls and A Farewell to Arms, and pet the cats that purportedly descend from his six-toed feline, Snow White. 

Another of Key West’s famous residents was Harry Truman. The then-president spent his winters at what became known at the Little White House. Today, the building is a museum where a one-hour tour provides insight into the home’s history, including its role in naval conflicts dating as far back as the Spanish-American War. 

Speaking of the Spanish-American War, a fort used in the conflict—as well as in the Civil War—can be found in Fort Zachary Taylor Historic Park, located on Key West’s westernmost point. Immerse yourself in the history of the fort on a guided tour. Afterward, hike, snorkel, bike, or fish at the park. There’s also a beach, but because it’s rocky, make sure to bring appropriate footwear. 

Eat 

After working up an appetite, head over to Duval Street to chow down on a sloppy-joe sandwich at Sloppy Joe’s bar. Named for its former bartender “Sloppy” Joe Russell, who was also Hemingway’s fishing guide, the bar is also a great place to check out live music.

 
For dessert, take a walk over to nearby Kermit’s Key West Key Lime Shoppe, a bakery and restaurant that serves delectable Key lime pie as well as the island’s signature treat, Key lime pie on a stick. Frozen and dipped in chocolate, it’s a great way to cool off on a hot day. 

Connect with Plants and Animals 

At the indoor oasis Key West Butterfly & Nature Conservatory, visitors will find more than 50 species of butterflies and a multitude of lush tropical plants. There are also 20 bird species, among them a pair of flamingos named Rhett and Scarlett.   

Another can’t-miss stop for plant lovers is the Audubon House & Tropical Gardens. Here, you can tour a verdant garden teeming with bromeliads, orchids, and other tropical varietals. Located in Old Town, the house is named for famed ornithologist John James Audubon, whose artwork is on display here. 

Watch the Sunset 

Some say you can see a green flash as the sun dips below the horizon off of Key West. The best place to observe this anomaly is Mallory Square, a popular spot located on the island’s northwest tip.  

Get here early to explore the free daily arts festival that takes place in the two hours before sunset, then grab dinner at Hot Tin Roof (the no. 1 restaurant in Key West, per Tripadvisor) or another surfside restaurant, like Latitudes on tiny Sunset Key, which lies about 500 yards from Key West. Make sure to plan ahead, however, as these eateries can be booked months in advance. Alternatively, take a cruise and watch the sun go down from out on the water.  

Relax on the Beach 

While not known for its beaches, Key West boasts ample sandy shorelines. The aforementioned beach at Fort Zachary Taylor Historic Park is on the rockier side, so those looking for a more traditional beach day should opt for Smathers Beach.  

Visitors here can splay out on the soft, sugar-white sand while enjoying shade offered by palm trees. Food trucks are nearby, as are bathrooms and equipment rentals.  

Visit the United States’ Southernmost Point 

Have your picture taken next to a multicolored buoy that marks the country’s southernmost point. The buoy, which reads “90 Miles to Cuba,” is adjacent to two plaques that provide important historical insight into Cuban exiles and the local Black community.  

Next, head over to the Key West Lighthouse. Along with offering views that look out toward Cuba, the top of the lighthouse contains history in the form of a museum located inside a 19th-century keeper’s quarters. 

Stroll Down Duval Street 

Sloppy Joe’s and Kermit’s Key West Key Lime Shoppe aren’t the only places worth visiting on Duval Street. Along this mile-plus stretch, travelers will find a variety of shops.  

There are also art galleries, a ghost tour, and plenty of other places to eat and drink. Get your caffeine fix at one of the multiple Cuban Coffee Queen locations, and munch on tapas at Nine One Five, a bistro whose front porch is a prime people-watching spot. 

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