4 Great Bars (& 1 Great Hangover Spot) in Key West

When I first set foot on Key West’s Duval Street, I was greeted by eccentric shops, themed restaurants, pink taxicabs and warm, inviting sunlight. I immediately knew that I was in for a unique experience. I spent a weekend there for a bachelor party, so the itinerary wasn’t really focused on visiting the cultural parts of the town, but simply on finding some great places to get lost in the revelry.

One such place is a small, friendly bar known as Flying Monkeys Saloon. The outdoor atmosphere makes for great people watching, and the small, yet roomy space makes it easy to mingle and make new friends. And don’t forget the frozen drinks, which are some of the absolute best. These cleverly named drinks include: Grape Ape (bourbon, 151 rum and grape punch), Howler (grain alcohol, vodka and lemonade), Ruby Roo (fresh raspberries and 151 rum) and, of course, the titular Flying Monkey (a mix of the Howler and the Ruby Roo). If you find yourself in Key West, be sure to make Flying Monkeys your first stop to get the party started. However, be advised that their drinks, while exceptionally good, are also quite strong. It probably wasn’t the best idea for me to have two Flying Monkeys in a row on an empty stomach while jet lagged. But hey … it was a bachelor party.

If you’d like to get some food in your system after your arrival, Willie T’s Restaurant & Bar is an excellent spot to do so. The menu consists of American and Caribbean cuisine with an emphasis on seafood. Our time at Willie T’s was both delicious and educational, as one of my fellow travelers and I learned how to say “thank you” in Russian. (Of course, this was done solely in an effort to garner the attention of the attractive Russian waitress tending to us.) One especially fun thing about Willie T’s is the seemingly infinite amount of one-dollar bills stapled to the walls, the ceiling, the bar and even the trees. It’s customary for first-time visitors to write their names on dollar bills so they can be immortalized within the restaurant. If you decide to visit Willie T’s, make sure you find the time (and space) to leave your mark. After you’ve done that, look for a dollar bill marked “Deech” on the wall leading to the outdoor patio to bask in my glory.

While Willie T’s has a full bar with great drink selections, Irish Kevin’s is a much more appropriate place for those looking for a traditional bar scene. It usually attracts plenty a crowd with its live music, great service and all around excellent dive bar feel. There’s no food menu, so it’s best to come here for after-dinner drinks and not-for-kids entertainment.

While we enjoyed the classic bar atmosphere of Irish Kevin’s, we found ourselves yearning for something with a bit more space. This led us to a lively, laid-back spot known as El Alamo. Like many other Key West joints, El Alamo is an outdoor bar with live music and a friendly crowd. However, what sets it apart is its bevy of outdoor games, which include cornhole, beer pong and flip cup. It also serves $1 PBRs and features a pool table in its small indoor shack.

Since our time spent on Duval Street was for a bachelor party, we decided to use the next morning to end it in the manliest way possible: with a breakfast consisting of crepes and mimosas from an adorable French cafe known as Le Creperie. Here you’ll find both savory and sweet crepes, both of which are highly satisfying. I chose to go with a crepe topped with bananas, strawberries and Nutella for a sweet end to an even sweeter weekend.

What’s your favorite spot in Key West?

— written by Mike DiChiara