Key West Bar Crawls
Hit Duval Street for the ultimate night out. With plenty of bars, clubs, pubs, eateries and restaurants to choose from, allow us to help you plan a personalized Key West bar crawl. Our local, knowledgeable team is happy to provide recommendations based on your personal taste.
While the Sun’s Still Up…
Start with Sloppy Joe’s, at 201 Duval Street. This infamous bar opened in 1933, on the day Prohibition was repealed. A favorite spot of Hemingway’s, the bar is known for live entertainment and for being open 365 days a year.
Next, head down the street to Fat Tuesday at 305 Duval. This open-air bar is a great place to visit any time. Grab a table in the courtyard and (at least) one of their notoriously strong frozen drinks, which come in t10 different tropical flavors.
To continue your evening, walk two blocks up to 524 Duval for more energetic vibes. At Virgilio’s, you’ll enjoy live music and tasty martinis in a dimly lit bar offering sunset views.
Hit up another legend, Captain Tony’s Saloon, at 425 Greene Street. Named for its owner and past mayor of Key West, Captain Tony Tarracino, this bar was a Jimmy Buffett favorite. Past patrons have included Presidents Truman and Kennedy, Elizabeth Taylor, Truman Capote and Tennessee Williams
When the Sun Goes Down…
For some fun, go up a bit further on Duval, to 801 Duval Street. The 801 Bourbon Bar is a dance club that features drag shows and cheap drinks. Feel free to join the fun on stage.
After the show, make your way down to 224 Duval to the Bull and Whistle Bar. With themed bars on each of the three floors, there is something for everyone. The drinks are strong, the dance floor is crowded and the bartenders are friendly.
If you feel like dancing, head down to 202 Duval Street. At Rick’s Bar, you’ll find live music and dancers at the Red Garter Saloon and a dance floor with a DJ at Rick’s Upstairs. For more ideas on where to go in Key West, browse our nightlife suggestions.
After the Bar…
Although it’s fun to party, always do so responsibly. If you’re too far from 0 Duval Street to walk back, please take a taxi.
Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and Sunset Pier.
Jun05Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.
Date: May 8 - June 26, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Jun06Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.
Date: May 9, 2026 - June 27, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Jun07World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - June 28, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Jun09Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - June 30, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Jun10Zero Duval Scavenger Hunt
Experience a one-of-a-kind, interactive scavenger hunt in the downtown area of Old Town, starting at Zero Duval.
Date: May 13, 2026 - June 24, 2026
Time: Wednesday's, 10:00 am – 12:00 pm
Location: Old Town Key West (starts at Zero Duval)
Jun11Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - June 25, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Jun11Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - June 25, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Jun11Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - June 25, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Jul23Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingway look-alikes
Date: July 23 - 27, 2026
Time: Varies by event
Location: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
