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A Guide To The Best Key West Dive Bars

Friends at the Green Parrot.

Dive bars – they hold a special place in the hearts of many. Come as you are, drink cheap, and have a great time. These classic Key West watering holes hit the spot when you want to kick back without care.

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!
428 Greene Street
Key West, FL 33040

 

Mary Ellen’s Bar
You can find Mary Ellen’s in a quiet alley right off Duval street. You come for the drinks and stay for the food. With a walk-up counter & famous for their grilled cheese & tomato soup, this place is perfect for a late-night meal after a night out on Duval. While here, enjoy the variety of live entertainment offered.
420 Applerouth Ln
Key West, FL 33040

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.
1 Duval Street
Key West, FL 33040

 

Half Shell Raw Bar
An authentic fish house In Key West’s Historic Seaport, you can eat and drink here while enjoying the view, as this place is located on the water. Featured on Travel Channel, menu includes oysters, clams, shrimp & more! Happy hour 4:30pm – 6:30pm.
231 Margaret Street
Key West, FL 33040


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!
601 Whitehead Street
Key West, FL 33040

Bobby’s Monkey Bar
A fun late-night spot that serves their cocktails strong, but cheap, includes plenty of karaoke & a very laid-back ambiance.
900 Simonton Street
Key West, FL 33040

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