The Quintessential Key West Bar Crawl

There’s something for everyone at the world-famous bars and nightclubs of Key West. Listen to live music, sample refreshing drinks or enjoy the casual ambiance. If you want to embark on the quintessential Key West bar crawl, check out the Key West Cocktail Challenge. Order a specialty cocktail at each of the six Pat Croce and Company establishments, including the Half Shell Raw Bar, Turtle Kraals, The Rum Barrel Bar and Grill, Island Dogs Bar, Charlie Mac’s 404 and the Green Parrot Bar, to receive a complimentary Cocktail Challenge shirt. Take as long as you would like to complete our challenge, and don’t forget to drink responsibly. Check out our recommended Key West Cocktail Challenge walking route to start your bar crawl adventure!

Image of Key West Cocktail Challenge Map

Stop #1: The Half Shell Raw Bar
Set in the historic Key West seaport at 231 Margaret Street, the Half Shell Raw Bar is a favorite spot for locals to enjoy the island’s freshest seafood. With delicacies like conch, oysters, shrimp and clams sourced daily from the restaurant’s own fish market, you’ll get a taste of old Key West that you can’t find anywhere else. Order their Oyster Shooter, complete with Jalapeno-infused vodka, a fresh oyster and a splash of cocktail sauce, and get ready to make the next stop on the Key West Cocktail Challenge.

Stop #2: Turtle Kraals
Located next to the Half Shell, Turtle Kraals is known for intimate waterfront dining, delicious entrees and tropical drinks. Settle in at Turtle Kraals’ Tower Bar for an unforgettable view of the historic Key West seaport and Key West’s famous sunset. Sample a tangy Key Lime Margarita, get a map punch and catch some of the restaurant’s one-of-a-kind turtle races if you’re there on a Monday or Friday night.

Stop #3: The Rum Barrel Bar and Grill
What could be better than enjoying refreshing drinks, eating delicious food and watching sports on big screen TVs? The Rum Barrel has all this and more, including a unique beer pong game machine for partying in paradise. Grab a signature drink off the Rum Barrel’s expansive menu, and head to the upstairs Quarterdeck to take in panoramic island views and great live music. The Rum Barrel is located at 528 Front Street.

Stop #4: Island Dogs Bar
Ready to relax and people watch? Stop by Island Dogs Bar, located at 505 Front Street, and take a seat on their breezy front porch. This is the perfect place to meet both Key West locals and tourists just passing by. Island Dogs encourages people to come as they are and revel in laid-back island living. Sample their signature Key Lime Pie Martini, receive a map punch and you’ll be nearly finished with the Key West Cocktail Challenge!

Stop #5: Charlie Mac’s 404
Next, you’ll find succulent, award-winning BBQ at Charlie Mac’s 404. With an array of smoky and sweet BBQ sauces to complement your meal, you can’t go wrong with some tasty pork sliders or brisket. Charlie Mac’s also offers one of the largest craft beer selections in Key West. If you arrive early enough, enjoy happy hour specials on drinks and appetizers during weekdays. Be sure to order Charlie Mac’s Huckleberry Lemonade before you leave to get a punch on your map.

Stop #6: The Green Parrot Bar
Finish your crawl right here at the Green Parrot Bar located near Duval Street at Southard and Whitehead Streets. Here, you can enjoy some of South Florida’s best live music, sample free popcorn and shoot pool while you mingle with locals. Sip our signature Root Beer Barrel, a shot glass filled with root beer schnapps inside a rocks glass filled with lager beer, to receive the final punch on your map. Then, present your completed Key West Cocktail Challenge Map for a complimentary t-shirt, and be sure to wear your bragging rights wherever you go!