Key West Island on the Florida Keys is truly an island city. By day, people scuba dive, ride jet skis, water ski, snorkel with the fish, lounge by the beach, swim in the turquoise water, explore the island or browse the boutique shops. By night, people go bar hopping downtown on Duval Street. And boy, do people go out. Every single night of the week, bars are totally packed—it reminded me of Ios town in the Greek Islands. Whether you like live music, a good dancing crowd, or a chill place to hang out with friends, Duval in Key West has it all. After a few nights of extensive research, here are my favorite top five best bars for variety, music, entertainment and island-fun.
Quick Tip: Key West allows you to drink and carry open containers of alcohol on the street.
Located on the corner of Greene and Duval Streets, Sloppy Joe’s is one of Key West’s oldest functioning bars. It has hosted people since 1933 and still rocks with great live music. Open 9 a.m. to 4 a.m., music starts around noon each day and you can enjoy a hearty pub-grub lunch menu. Later on in the night, bar staff move the tables and a larger band takes the stage. Music ranges from rock to soft metal and the floor becomes a small venue for a concert. If this atmosphere is too rowdy for you, visit Joe’s Tap Room, a smaller room featuring specialty beers on tap, the same menu and a satellite TV.
This is actually the smallest bar I’ve ever been in. It probably holds about four or five people comfortably, and there is standing room outside. The bar is set up so the bartender is in the back (his bench is about four feet wide) and you form a line next to the sunset mural to get drinks. Definitely worth a stop by—they have the best house tequila I’ve ever tasted. It’s a great in-between place to stop for a drink while you’re deciding where else to go.
Tucked behind Duval Street at 4 Charles Street, the Alamo is a large open-space, locals hang out. Most tourists don’t go here and I heard about it from one of the local guys leading our first jetski tour. I stopped by here two nights in a row and both nights El Alamo hosted great live music: Thursday featured a one-man vocalist and Friday featured an acoustic guitar ensemble with three singers. You can play pool, flip cup and beer pong here.
It might seem weird to be drinking at an Irish bar in Key West, but Irish Kevin’s is definitely no disappointment. You can tell the quality of an Irish bar in America by the way the bartender pours a Guinness. If tenders let the beer settle for a few minutes (pouring it slow), they just might know their stuff. The bartenders at Irish Kevin’s were both very attentive, and they poured a nice Guinness. Double bonus. It’s one of the larger spaces on Duval Street and a great place to go with a big group for a louder atmosphere.
Ladies, you drink free here on Thursday nights from midnight until close. It’s located right on Duval Street next to Sloppy Joe’s and makes a great addition to the Key West bar hopping chain. This is one of the best happy hour places: on Sunday and Monday nights happy hour runs from 5 p.m. to midnight. Happy hour is two for one on bottled beer and $5 daiquiris. Also check back for seasonal and week night drink specials. This is a great place to go if you’re traveling on a budget.