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A Guide To The Best Key West Dive Bars

Captain Tony's Key West Dive Bar

The crew at Captain Tony’s.

by Shayne Benowitz

Dive bars. They hold a special place in the hearts of many. Come as you are, drink cheap, and have a great time. Although not always my cup of tea, I’ve definitely had some great times in the local dives. These classic Key West watering holes hit the spot when you want to kick back without care.

 

 

Outside Captain Tony's Dive Bar

Captain Tony’s

The site of the original Sloppy Joe’s where Hemingway used to hang is located right off Duval Street on Front. It’s a dark hole in the wall with pool tables, the occasional live musician, and walls lined with memorabilia. Named for a much-loved and somewhat infamous Key West character, Captain Tony’s is a great spot for some trouble. It’s one of Captain Westy’s favorites. We like to grab the benches around the unused fireplace and if we’re feeling frisky we’ll order up a round of the house specialty rum punch. They’re tasty with a distinct pineapple flavor and they come in cool souvenir cups!

 

 

Chart Room Key West Dive Bar

Chart Room

This little hideaway is tucked into the Pier House Resort. It’s small, dimly lit, lacking ambiance, but flush with peanuts, free hotdogs, and a fun dice game. Things get silly at the Chart Room. Sit at a large round table with your friends and order up a round of Jack & Cokes or some bottled beers and play Ship, Captain, Crew. All you need is the dice and a bunch of dollar bills.

 

 

Green Parrot

There’s nothing secret about the Green Parrot, one of the most loved and frequented bars amongst locals and tourists alike. Whether it’s live music on a Saturday night, midday beers, happy hour, or closing it down at 4am, the Parrot is always full of surprises. My favorite memories have been quieter nights with a good group of friends playing darts, drinking beer, eating popcorn, and of course a few rounds of root beer barrels!

Shayne Benowitz is a Fury crewmember and freelance writer. For more travel stories and a daily dose of what’s cool around the globe visit her Wanderlust Website at http://web.me.com/shaynebeth.

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