A Resident's Guide to Nightlife in Key West

If you’ve ever visited Key West, you’ve probably walked Duval Street and popped into the many bars, restaurants, shops, and art galleries on the strip. You also likely went to Mallory Square to enjoy the entertainment and sheer spectacle of the daily celebration surrounding the sunset.

This quirky island—the last in the chain of islands known as the Florida Keys—attracts throngs of tourists each year. But it’s also home to locals, who work and live on the island. Though locals of the Conch Republic—affectionately referred to as “conchs”—enjoy a night out at Sloppy Joe’s rubbing shoulders with the people who bring vital dollars to the island, they also like to party with fellow locals and swap stories about life on the island.

While outside the coverage of Neighborhoods.com, Key West has some places especially popular with residents. Here are the spots to check out, if you want to party like a local.

Schooner Wharf Bar

Schooner Wharf Bar photo by Shutterstock

Located at the foot of William Street on the city’s Historic Harbor Walk, Schooner Wharf Bar is popular with locals due to its rustic charm, food, and music. The bar is the home port of the Key West flagship Schooner Western Union, which is available for sunset cruises and private parties. It’s also the site of numerous special events throughout the year, including the Lighted Boat Parade in December, the Minimal Regatta over the Memorial Day weekend, Wrecker's Cup Race Series, and one of the Keys' favorite events, the Battle of the Bars.

The Green Parrot

If you ask where the locals hang out, the Green Parrot is most likely at the top of the list. Located at the corner of Whitehead and Southard streets, it features live music on the weekends and a “come-as-you-are” atmosphere. It describes itself as “a jury of non-judging peers, a rugged and ragged council of friends” and over the years has hosted everything from poetry slams to divorce parties.

Captain Tony’s Saloon

Captain Tony's Saloon photo by Shutterstock

Dubbed the oldest bar in Florida (it opened in 1851), Captain Tony’s Saloon is frequented by locals who have been coming here for decades. It’s reported to have been frequented by such legends as Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein, and Jimmy Buffett. Including serving as a city morgue when it was first constructed, the saloon’s history is as colorful as the many bras that hang from its ceiling.

Bottlecap Key West

Located at 1128 Simonton St. near “the quiet end” of Duval, Bottlecap Key West is an out of the way spot that many tourists wouldn’t even recognize as a bar. It describes itself as a “Cheers”-like bar with a cozy patio area, virtual jukebox, pool table, and liquor to go. Come by for Comedy Key West on Thursdays and Fridays in the Blue Room, which also hosts private parties.

The Bull, Whistle Bar, and the Garden of Eden

Whistle Bar photo by Shutterstock

These three bars are located within one building at the corner of Duval and Caroline. Each bar occupies one floor with a personality all its own. Here, the walls tell a story in hand-painted murals of the people, places, and events that make up the history of this open-air bar which many still consider a part of the city’s Old Town Heritage. But the patrons, many of whom are locals, also tell their own stories, and they get more interesting the more stairs you climb. The Bull, on the first floor, has live music, and the Whistle has an outdoor seating area around its edge that’s perfect for people watching. And those who climb their way to the third floor enter the Garden of Eden, the city’s only clothing optional bar. There, you’ll find people in various states of dress, along with the onlookers and, invariably, a few dazed tourists who stumble into the bar unaware of its dress policy.

Virgilio’s

Although it’s right on Duval Street (and therefore attracts its fair share of tourists), Virgilio’s is still considered a hot spot for locals. This martini bar features classic cocktails (including $5 Martini Mondays), live music, and late night dancing in the garden bar. Unlike other local bars, this is definitely not a dive bar; in fact, many are drawn to its classy atmosphere and wide array of martinis on the menu.

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