By Lauren Tjaden

Notorious. Epic. Legendary.  

That’s Duval Street in Key West, a quirky, free-spirited place where roosters roam among the tourists and historic buildings, where normal concerns and decorum dissolve in the tropical breeze.  

A mere 1.25 miles long, Key West’s main drag is nicknamed “The Longest Street in the World” as it runs the entire distance from the Gulf of Mexico to the Atlantic Ocean. This stretch of pavement has rightly earned a reputation as party central with its menagerie of boisterous bars – a higher number per capita than any other place in the country -- but it’s more than that; it’s the beating heart of the Conch Republic, brimming with eclectic shops, art galleries, eateries and attractions.

Sloppy Joe’s Bar is inextricably linked with Key West’s most famous resident writer, Ernest Hemingway, and a band of colorful characters; it remains an authentic slice of Old Town.


I’m here for the party

All the stories you’ve heard about Duval’s no-holds-barred craziness are mostly likely true, and when the sun goes down the block wakes up, with throngs of people filling the sidewalks, music spilling into the street, and iconic bars packing a potent punch.

Completing the infamous Duval Crawl isn’t a journey to be undertaken lightly – or in one night – as at last count 43 bars populate the road, in addition to numerous restaurants that serve drinks.

Favorites include the oldest bar in Key West, Captain Tony’s Saloon, constructed in 1851 as an icehouse that also served as a morgue and much-loved by characters including Ernest Hemingway, Truman Capote, and Jimmy Buffet; Sloppy Joe’s, a historic location that promises food, live music and dancing (check out their crowd cam); and Hog’s Breath Saloon, an uninhibited establishment that offers daily live entertainment, a raw bar and food.

Not to be outdone, Rick’s Bar encompasses eight different bars and declares itself to be ‘the largest drinking establishment in the Florida Keys,' while the Smallest Bar Inn covers the other end of the spectrum at 72-square-feet, about the size of a jail cell.

If you’re feeling overwhelmed with the choices, book a Duval Crawl tour, a lighthearted, 2.5 hour guided tour that includes five cocktails and a souvenir t-shirt. Or take the Green Parrot Bar’s Key West Cocktail Challenge, with six stops on their recommended walking tour.

Take a selfie at the Southernmost Point, the colorful concrete buoy that denotes the southernmost point of the continental United States, a mere 90 miles from Cuba.


See the sights

It seems everyone who’s ever visited Key West has a picture of themself at the Southernmost Point, the colorful concrete buoy that denotes the southernmost point of the continental United States, a mere 90 miles from Cuba. Join the tradition near the southern end of Duval (at Whitehead Street and South Street).

The Key West Butterfly & Nature Conservatory is a must-visit, inviting you to take a stroll through a lush, tropical paradise of flowering plants and cascading waterfalls populated with hundreds of living butterflies and colorful birds. It also features a learning center, gift shop and art gallery.

 Mallory Square, located off the northern tip of Duval, provides another beloved Key West ritual, its nightly sunset celebration, where crowds gather about two hours before Mother Nature provides the showstopper event. Street entertainers fill in the gaps. On any given evening, you might see a highwire unicycle act, musicians, or a fiery-sword swallower. And then there’s Catman, who shows off his house pets in what’s billed as the "best cat show on Earth." The hype isn’t for nothing; these talented felines walk tightropes and jump through rings of fire in a fascinating comedy performance.

There’s more; the nearby Hemingway House and Museum, the Key West Aquarium in Mallory Square, and even the Walgreens are worth a visit—the latter is housed in the historic Strand Theater, complete with a restored exterior and decorative figurines.

A ride on the Old Town Trolley will introduce you to the town on a fully-narrated, 90-minute sightseeing expedition. You can hop on and off at the sites you’re interested in and find out about the rest.

A taste of paradise

When it’s time to refuel, Duval’s diverse eateries ensure you’ll leave satisfied.

La Trattoria serves up a romantic, bistro-style experience along with authentic Italian fare, locally-caught seafood, and craft martinis accompanied by live music. For a special treat, try the Nine One Five Bistro, an upscale affair set in a stunning Victorian-era home that treats the palate with offerings like grilled octopus, crisp bacon wrapped dates, and a seafood soup swimming with Key West pink shrimp, clams and local snapper; or LaTeDa, promising open-air fine dining in a casual atmosphere and delivering dishes like Crispy Lacquered Duck, Sautéed Key West Yellowtail Snapper and Stuffed Chicken.

For quick fare, head over to DJ’s Clam Shack, which earns high marks for its affordability and mouth-watering menu of Stuffed Lobster Roll, Mahi Mahi Tacos and Conch Fritters; or Fritas Cuban Burger Café, offering their signature Fritas as well as classic Cuban sandwiches and tacos.

Here are places to eat centered around Duval Street from OpenTable.

Places to stay

To explore all of Duval, never mind Key West, you’ll need more than one day. Check out these places to spend the night, ranging from intimate B&B’s hugging the Atlantic to famed resorts set amidst the backdrop of pubs, stores and restaurants.

At the quieter end of Duval, the Southernmost House Hotel is an acclaimed adults-only B&B constructed as a private residence in 1896. Sited on the Atlantic Ocean, it’s complete with wraparound porches and a private pool. Nearby, the Southernmost Beach Resort is a simple yet sophisticated resort that blends historical charm and modern facilities.

Other offerings include the Crowne Plaza Key West La Concha, located in the core of Duval and holding bragging rights as the tallest building on the entire island; the New Orleans Guesthouse, the only gay, all-male hotel on Duval; and the unassuming 24-room Orchid Key Inn, featuring a tennis court and an outdoor swimming pool.

On Duval’s northern point, The Pier House Resort, tucked next to the Gulf of Mexico, has been providing island-chic accommodations for over 40 years, with a private beach, spa, bars and dining; while the award-winning Ocean Key Resort and Spa promises stunning views of emerald-hued waters and private, furnished balconies.

Here are places to stay on and near Duval Street from TripAdvisor, and places to stay in Key West from its visitors’ services.

How to get around

You should ditch the car keys as parking can be challenging on Duval Street and plenty of other ways to get around exist.

Walking is a great option, as Duval is only a smidge over a mile long and all of Old Town is less than two square miles—and it’s pancake-flat.

Bicycling is another popular choice, and you can rent one-speed beach-style bicycles, known as ‘Conch Cruisers’ at a number of places for about $50 a week.

Or hop on the free bus, courtesy of the City of Key West.  Its ‘Duval Loop’ features 18 stops, providing simple access to numerous points of interest. Buses run frequently. Check out a map and information about the Duval Loop Bus.

You can leave your wheels at Key West Park N’ Ride, situated on the corner of Grinnell and Caroline Streets, for $4 per hour or a $32 maximum daily fee. Your Park N’ Ride Garage ticket entitles you and everyone else in your vehicle to ride the city routes of public transportation in Key West for free.

Famed festivals include Hemingway Days, a July extravaganza featuring scores of bearded Hemingway look-alikes.


Events and Festivals

Check the calendar for major events before you go, as they’ll mean huge crowds on Duval Street… and also huge fun, if you want to be part of the action.

Famed festivals include Hemingway Days, a July extravaganza featuring scores of bearded Hemingway look-alikes; Fantasy Fest, an annual ten-day party for grownups held in October; and the Conch Republic Independence Celebration, a wacky commemoration of the very brief 1982 secession of the Florida Keys from the United States. The Key Lime Festival takes place late June to early July each year, honoring citrus, eccentrics, people and pie; while every August, Key West Lobsterfest celebrates local seafood with the biggest party of the summer.

When you go…

For places to stay and eat, things to do, transportation information and events, check out Key West’s visitor’s services.

Places to Remember