A Locals' Guide To The Perfect Key West Bar Crawl
While the name Key West often conjures images of picture-postcard beaches and clear waters that are as warm as a bath, it's also famous for its raucous nightlife. Many of Key West's famous residents enjoyed a tipple or two, and so do most of its visitors. Whether you want to make like Ernest Hemingway and sip on a Papa Doble (a Hemingway Daiquiri) or follow in Truman Capote's footsteps with a screwdriver, you'll find somewhere to imbibe in Key West.
But where to go on your Key West bar crawl to experience a bit of local life? As the sun sets in this tropical paradise, the vibrant nightlife scene really gets going, and tourists and locals alike pour into the streets. One of the top watering holes is the Green Parrot Bar; many local Redditors in the r/KeyWest forum name it their favorite bar. It's a self-proclaimed icon of Key West, is open seven days a week until 4 a.m., and features live music, happy hours on weekdays, and Monday night bingo. Start here, end here, just go here.
The local experience
Key West locals in the r/KeyWest forum on Reddit name Don's Place as the ultimate dive bar in the area. Don's considers itself a local bar for tourists, so everyone's welcome, though Redditors say that there are usually more locals than visitors. There's an outdoor tiki bar, numerous televisions to watch sports, and places to play games. Don's is open from 7 a.m. to 4 a.m., so you can tip up pretty much any time and enjoy the cheap drinks.
Other popular and lively local recommendations include Mary Ellen's Bar and Kitchen, as well as General Horseplay. Mary Ellen's is a good place to get something to eat — mainly sandwiches and snacks — and they often have live music and other events. On Thursdays, Mary Ellen's runs the famous charity Vibrator Races (it's exactly what it sounds like, they race vibrators), and you'll be expected to join in the fun if you're there. Don't take the kids. General Horseplay is home to a crowd of younger locals, according to Reddit, with one local saying it has the best cocktails and music on the island. The bar's tagline is "cocktails [and] tomfoolery," so you know what you're getting.
Laid-back vibes
It's all relative in the party town of Key West, but if you're looking for a slightly more chilled-out vibe, there are several bars to check out. Many of them claim to give patrons a taste of the old Key West and locals flock to them. First is Schooner Wharf Bar, which offers visitors stunning views over the seaport, an extensive menu, and daily entertainment as well as three happy hours, one of which is from 2 a.m. to 4 a.m.
Hogfish Bar & Grill is on Stock Island, so it's physically distant from the main Key West party area. It also tries to distance itself in terms of atmosphere, too. " ... [T]he Hogfish Bar and Grill is a true 'locals' spot that avoids the pretension and hype of more touristy areas," claims the bar's official website. They serve fresh seafood, so it's a great place to grab a bite and a cocktail.
For real old-school Key West charm, Redditors in the r/KeyWest forum recommend Chart Room. The bar is now in the luxury Pier House Resort but has kept its down-to-earth charm. "As the unofficial headquarters of Mel Fisher and Jimmy Buffett, Chart Room holds the key to countless Key West tales and memories," reads the bar's official website. Chart Room serves straight-up spirits and strictly enforces a non-straight-up dress code, so come casual.