The 15 Best Things to Do on Duval Street in Key West

They don’t call it the Duval Crawl for nothing. Start at one of the more infamous watering holes like Sloppy Joe’s, Captain Tony’s Saloon, or the Key West First Legal Rum Distillery. Order a cold drink, listen to a little live music, and then stroll over to the next fine establishment on the block (there are dozens!).

No this isn’t Pamplona, it’s Key West. Every summer Ernest Hemingway look-alikes ride a manmade bull on wheels in a parade during the annual Hemingway Days festival. The Pulitzer Prize-winning author lived and wrote in Key West throughout most of the 1930s.

Whether you’re in the market for a mini buoy modeled off of the Southernmost Point, or a slightly offensive, only-in-Key-West statement T-shirt, there are plenty of souvenir shops that line Duval Street. Or check out one of the elegant local boutiques like Terra Nova, where you can find island-style wraps and stylish resort wear.

If you’re into the paranormal, then you’ve come to the right place. Key West is home to its fair share of ghoulish haunts like the town’s oldest graveyard, historic Victorian mansions and more. The local ghost hunters say even the Hard Rock Café is haunted!

Join the crowds at Mallory Square for a nightly sunset celebration. As the sun sinks into the sea, you’ll find acrobats, guitarists, sword swallowers and entertainers like Will Soto performing his juggling high wire act.

It’s completely acceptable to wear costumes year-round in Key West. But the atmosphere gets extra festive during the annual 10-day Fantasy Fest every October. More than 50,000 costumed revelers descend to Duval Street for a flamboyant parade and party.

Near the end of the 19th century, wealthy business owners began constructing pastel-colored Victorian mansions that many today describe as Key West-style architecture. Spend the night in one of these historic homes and book a room at the Southernmost House, both a hotel and a museum, located at the southern end of Duval Street.

Renting bicycles and cruising down Duval is a great way to explore the entire stretch from end to end. Start at the Southernmost Point and then ride up the strip all the way to Mallory Square on the north end. You’ll find plenty of places to stop along the way.

Home to an active and fun-loving LGBTQ community, Key West is a great place to check out a drag queen show or two. On Duval Street, talented divas perform nightly shows at Aqua Nightclub, La Te Da, and 801 Bourbon Bar.

Because of its colorful history and tropical landscape, Key West has attracted international artists from around the world for years. Browse through island-inspired collections at places like the Peter Lik Gallery at 519 Duval Street. 

Did you know that around 40 six-toed cats live at the Ernest Hemingway Home and Museum? Legend has it that the writer was given a white six-toed cat by a ship's captain and the legacy lives on. At the home, you can also go on one of the daily tours to learn about the life and times of one of Key West’s most famous residents.

Key lime pie is the signature dessert of the quirky island. Equal parts sweet and tart, it’s a must-try at Kermit's Key West Key Lime Shoppe on Duval Street.

Perfect for families (kids 12 and under ride free!), the 90-minute Conch Train Tour has been introducing visitors to the unique aspects of Key West since the 1950s. The tour departs from the Front Street Depot, makes a loop through Old Town Key West, and ends right behind Mallory Square.

If you’re an aficionado of all things weird, then you’ll want to visit the strangest place in all of Key West. Ripley’s Believe It or Not Odditorium is home to more than 500 peculiar exhibits like a statute of Captain Jack Sparrow made from recycled car parts.

While it’s now the restored façade of a convenience store, The Strand Theater was a popular place for live shows in the 1920s, and it’s the perfect backdrop for a unique photo. Or head over to the Southernmost Point to snap a tourist-style selfie. Be on the lookout for one of the many wild roosters that roam the island and snap a pic—if you can catch it in time!