Crawl 'Til Ya Fall: Key West's Duval Crawl

Crawl 'Til Ya Fall: Key West's Duval Crawl

Posted in Entertainment on October 04, 2017

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If you've ever been on Duval Street in Key West, you know it's always a party! If you haven't yet experienced the madness, it is definitely a must. In the wake of the devastation caused by Hurricane Irma, bars, restaurants, and small businesses in Key West are OPEN, and it's a great time to head down and support them as they rebuild! USA Today recently reported that the first cruise ship post Irma docked in Key West on 9/24, and it was back to business (read: fun) as usual.

Duval St. runs through Key West from North to South, starting at the Gulf Of Mexico, and ending at the Atlantic Ocean. It is a 1.25 mile street zoned for commercial use, and contains roughly 43 bars! It has long been a Key West tradition to sample a cocktail in as many of these places as possible in the course of a day - hence the name, The Duval Crawl. Did we mention that the bars open and festivities begin at 9am daily? Live bands inside and out, DJs, stand up comics, dueling pianos - every place has it's own form of entertainment. Add in the fact that the town is bursting at the seams with tourists & cruise ship passengers, and you have one constant giant party going on. There are tour companies that will guide you on your crawl based on your likes/dislikes and how much time you have, or you can just do what we did and pick a spot and get right to it with your first drink! As the clock in Sloppy Joe's says, "It's always 5 o'clock in Key West!"


It's a good idea to get some food in your stomach before the bars open (if you're starting early). A great place for breakfast is the oldest cafe in Key West, Pepe's Cafe. They have been serving hearty food since 1909 at their 806 Caroline St. address. Their homemade breads, custom omelets, pancakes and grits are all delicious. They open at 7:30am and have a full bar. Start off the day with a fresh squeezed mimosa!

Sloppy Joe's

Sloppy Joe's is a true Key West institution. Long associated with writer Ernest Hemingway, the bar went through two name changes and a move across Duval St. to the present location. The 80-year-old establishment features a huge curved bar, enormous stage where live bands play all day & night, and in July they host an Ernest Hemingway look-alike contest. Head to the corner of Duval and Greene St. for a great place to start your crawl.

Captain Tony's Saloon

Once you've finished up at Sloppy Joe's, cross the street to Captain Tony's Saloon. Known for their Pirate's Punch, which is basically a rum bucket, the ceiling is covered with signed bras from previous patrons! There's always live music to enjoy at this dive bar located on the opposite corner from Sloppy Joe's.

Smallest Bar

Located in a very crowded part of Duval St. is the Smallest Bar. The name doesn't lie, as it's an alcove really, with just a couple of bar stools. It's definitely a good spot to stop for a quick drink and a picture and keep on movin'!

Irish Kevin's

Just a little south of Sloppy Joe's at 211 Duval Street is Irish Kevin's. This was my favorite! This Irish pub was big, loud, and a ton of fun. Bradd Shadduck, the singer/standup comic, was hysterical! He really got the crowd going and tortured anyone passing by outside that wouldn't come in for a drink. The beer list is extensive - another great reason to stop.

The Bull and Whistle Bar

The Bull And Whistle Bar is at 224 Duval St. The inside bar on the first level is known as The Bull. The second story has large balconies where you can sit and people watch and is known as The Whistle. The rooftop garden is called the Garden of Eden, and clothing is optional.

Green Parrot Bar

We took a little detour off of Duval to 601 Whitehead St to have a cocktail at the Green Parrot Bar. There's always something going on here to accompany the cocktails, beer, and free popcorn. They host bingo nights (with all proceeds going to local charities), ukulele nights, and all kinds of live music. Lots of locals share Key West stories and keep coming back here. Need we say more?

The Best of the Rest:

There are way too many hot spots on the Duval Crawl to review individually, but here is a list of some others to try.

  • Rick's Key West - 202 Duval St
  • Lazy Gecko - 203 Duval St.
  • Flying Monkeys - 227 Duval St
  • Fat Tuesday - 305 Duval St
  • The Rum Bar - 1117 Duval St
  • Cork and Stogie - 1218 Duval St

So grab a map of Duval Street, and start crossing places off as you partake in this Key West tradition!

Written by Jeanne Maria

After years of working hard, Jeanne now just does what she wants. Painting, writing, traveling, daily beach walks with her puppy, and the occasional cocktail make her a very happy person. Life is too short, make a long bucket list and get to it!