Sloppy Joe's opened its doors to alcohol-swilling patrons on December 5, 1933, the very day Prohibition ended. This dedication to selling spirits to the masses has persevered ever since, and the bar has earned legendary status in Key West, making it a must-stop destination for all lovers of drink who've stumbled their way onto the island. The bar's most famous patron is easily Ernest Hemingway, who frequented Sloppy Joe’s during his stint on the island in the 1930s. Today the bar is home to the annual Hemingway Lookalike Contest, held during the Hemingway Days Festival every July. The bar remains open 365 days, from 9 a.m.-4 a.m. (noon-4 a.m. on Sundays). Live bands entertain nightly and food – hamburgers, salads and the like -- is on the menu, though, let's be honest, you're really here for the booze.
The good folks of Key West like to celebrate watching the sunset like it’s a national holiday … only one that occurs daily. One of the island's prime spots for bellying up while experiencing nature's spectacle is the Schooner Wharf Bar, which overlooks the water at the island's Historic Seaport. Drinks of choice include rum runners, daiquiris and the Schooner Breeze, a heady concoction of 4 flavors of rum, cranberry and pineapple juice. Fresh seafood lovers will be tempted to compliment their beverage with the bar's fresh-shucked oysters, pick-and-peel shrimp or stone crab claws. If watching the sunset isn't your thing, the bar also offers a schedule of live music and magic shows to entertain the masses.
Get more bang for your drinking dollar at The Bull & Whistle Bar -- technically 3 bars in 1. On the ground floor of the Duval Street structure you'll enter The Bull, a dimly lit, open-air bar painted with murals of old Key West, and typically quite crowded. The Whistle Bar, located on the building's second floor has a quieter, breezy ambience, featuring large windows and doors that open onto a wraparound balcony perfect for people-watching the crowds below on Duval Street. Finally, for the risque at heart, there's the Garden of Eden, a co-ed, clothing optional rooftop bar. A nightly roster of live music at the downstairs bar gets the crowd dancing, while pool tables can be found at the Whistle Bar. Check the website for printable 2-for-1 and $1 drink coupons.
"Hog's breath is better than no breath at all," or so the saying goes at the Hog's Breath Saloon, a Key West drinking landmark since it opened in 1976. Sure, the drinks are strong, the food, including conch fritters and fish nuggets, is decent and the crowd is dotted with locals … but really, patrons wrangle to converge here for epic events like an annual Homemade Bikini Contest and the Hair of the Hog Leather & Lace Contest, featuring a Bloody Mary breakfast. Both events are held during the island's Fantasy Fest at the end of October.
One of Key West's most popular gay bars, the Bourbon St. Pub opened in 1995 and morphed into a complex comprised of 4 bars, including the outdoor Garden Bar and pool area, which is men-only and clothing optional. Should you find yourself not willing to leave the action at night's end, book a room at the New Orleans House, an all-male guesthouse attached to the complex, featuring rooms overlooking the pool area. The pub hosts nightly entertainment and events, including male go-go dancers, pool parties and an annual Mr. Pride contest. If you're visiting Key West on New Year's Eve, head outside the pub to ring in the New Year -- Bourbon St. features a "drag queen drop" at midnight, when a drag queen named Sushi is lowered from the building's roof to the street in a gigantic red high-heeled shoe.
If the hordes of tourists choking Duval Street become too much to handle, seek respite at the Green Parrot, tucked away on Whitehead Street, just a block off of Duval. Open in various iterations (a grocery store then bar) since 1890, the Parrot attracts an "old salty dog" crowd of locals and fishermen, with a smattering of tourists lucky to have found the much beloved dive bar. A jukebox keeps the mood lively, featuring all manner of artists -- from Van Morrison to The Temptations, though the bar also offers live music and an ever-changing schedule of funk, R&B, zydeco and blues bands. Grab a bite to eat before arriving; aside from doling out free popcorn, the Green Parrot is a drinks-only establishment.