Best Nightlife Spots

Best Nightlife Spots, Key West, Florida (D)

Partying is a way of life in Key West. After watching the world's most famous sunset, you will want to be the one who knows where the popular spots are in Southern Most City. Key West offers a wide range of entertainment, on Duval Street and off the beaten path. This guide will help you find the best spots for nightlife in Key West.
Image Courtesy of Stacy Stepanovich.
This article is featured in the app "GPSmyCity: Walks in 1K+ Cities" on iTunes App Store and Google Play. You can download the app to your mobile device to read the article offline and create a self-guided walking tour to visit the attractions featured in this article. The app turns your mobile device into a personal tour guide and it works offline, so no data plan is needed when traveling abroad.

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Attractions Map

Guide Name: Best Nightlife Spots
Guide Location: USA » Key West
Guide Type: Self-guided Walking Tour (Article (D))
# of Attractions: 11
Author: Stacy Stepanovich
Author Bio: Stacy Stepanovich is a writer who lives aboard a 47 foot Concorde motor yacht in St. Marks, Florida. She has a MFA in Creative Writing from Goddard College and a BA in English from the University of Pittsburgh. She has extensively traveled the coastal waters of Florida and the Abacos during her eight years of living aboard.
Author Website:
Sight(s) Featured in This Guide:
  • Dante's Restaurant and Raw Bar
  • The Garden of Eden
  • Hog's Breath Saloon
  • Captain Tony's Saloon
  • Irish Kevin's
  • Sloppy Joe's
  • Schooner Warf Bar
  • The Half Shell Raw Bar
  • Key West's Smallest Bar
  • The Sports Page Bar and Grill
  • The Bull and Whistle
Dante's Restaurant and Raw Bar

1) Dante's Restaurant and Raw Bar

Famous for their Halos and Horns Party during Fantasy Fest, Dante's is the place to stay cool even when it's hot. The large pool and fountain at Dante's allows you to eat and drink while relaxing with a view of Key West Bight Marina. Stop in and choose a drink from the "Frozen Favorites" menu. From the Mango Daiquiri to the Perfect Margarita, you can't go wrong.
The Garden of Eden

2) The Garden of Eden

Located on the rooftop of the Bull and Whistle Bar, the Garden of Eden is Key West's only clothing optional rooftop bar. Famous for their body painting artists, check your inhibitions at the door before you ascend to the Garden of Eden.
Hog's Breath Saloon

3) Hog's Breath Saloon

Named after the saloon’s slogan, “Hog’s breath is better than no breath at all,” the Key West version of this Ft. Walton Beach classic opened in 1988. Whether your interested in a “Hair of the Hog” or the Homemade Bikini Contest, Hog’s Breath Saloon is known for great food, live music and outstanding drinks. Just steps away from the crowds of Duval Street, the Saloon offers indoor and outdoor seating where you can enjoy one of their signature drinks like the “Hogarita” or “Hog Wash” or their own special Hog’s Breath Brew.
Captain Tony's Saloon

4) Captain Tony's Saloon

What is now known as Captain Tony’s used to be the hang out of author Ernest Hemigway. Aside from being the original location of Sloppy Joe’s, 428 Greene Street was once a wireless telegraph station during the Spanish-American War, a cigar factory, a bordello and the oldest licensed saloon in Florida. The establishment was renamed in 1958 one last time for its owner, Captain Tony--a charter boat captain and former gun runner. Inside Captain Tony’s you can enjoy their famed “Pirate’s Punch” while listening to great live music. With walls that are covered with everything from business cards to undergarments and a tree growing through the ceiling of the saloon, Captain Tony’s has an atmosphere that is unmatched in Key West.
Irish Kevin's

5) Irish Kevin's

Home to the Key West Songwriters Festival and the Best St. Patrick’s Day celebration in the Keys, Irish Kevin’s is home to over a dozen of the best musicians the island has to offer. With great live entertainment all day, everyday, Irish Kevin’s has earned the right to boast “live entertainment at its best.” Stop in for a perfectly poured Guiness and maybe you’ll be lucky enough to see Irish Kevin himself performing on stage!
Sloppy Joe's

6) Sloppy Joe's

Sloppy Joe's is open everyday of the year from 9AM-4AM, Sloppy Joe’s is a must-see for any Key West bar-hopper. With live entertainment daily, generous pours and a casual atmosphere, it’s easy to spend a whole afternoon watching the crowds walk down Duval and Greene Streets through the white jalousie doors. Sloppy Joe’s first opened in 1933, the day Prohibition was repealed. Originally located where Captain Tony’s is, Sloppy Joe’s relocated to its current spot in 1937. The annual Hemingway look-alike competition brings hundreds of men vying to look the most like Key West's beloved "Papa." Whether you are in the mood to listen to live music in the main bar, or watch sports in "Joe's Tap Room," Sloppy Joe's has something for everyone.
Schooner Warf Bar

7) Schooner Warf Bar

A true piece of old Key West, the Schooner Wharf bar is located on Key West's Historic Seaport. This open-air bar and restaurant originally got its start upon the Schooner Diamante. Day or night, you can find a range of entertainment from storytellers to funk and rock bands. There is no shortage of "characters" at the Schooner Wharf. Be sure to check out the spectacular view of Key West Bight from the upper deck.
The Half Shell Raw Bar

8) The Half Shell Raw Bar

With the motto “Eat it Raw,” it’s no surprise that the Half Shell Raw Bar has an infamous oyster shooter. There’s even a Facebook group for survivors of the shot that combines a raw oyster with cocktail sauce and Absolut Peppar Vodka. The Half Shell Raw Bar was once a shrimp packing building and has maintained the feel of a working waterfront. With perfect views of Key West Bight, it is a great place to get a feel for old Key West while enjoying a signature cocktail like “It’s 5 O’clock Somewhere” or the “Raw Bar Rita.”
Key West's Smallest Bar

9) Key West's Smallest Bar

Officially the smallest bar in Key West, this location is a famous hot spot on Duval Street. Located at the Old Customs House, the Smallest Bar serves great drinks at cheap prices. It's a custom when hanging out in the smallest bar to encourage passers-by to "Come in and have a drink!" See how many people you can pack into Key West's Smallest Bar!
The Sports Page Bar and Grill

10) The Sports Page Bar and Grill

The name goes without saying, but the Sports Page Bar and Grill is the perfect place in Key West to watch a ball game and drink a cold beer. With two happy hours daily, the first from 4-7 and the second, a late night happy hour starting at 11PM, the Sports Page is a great place to grab a late night meal or enjoy any number of regular drink specials.
The Bull and Whistle

11) The Bull and Whistle

Located at the corner of Duval and Caroline Streets, the Bull and Whistle Bar is one of the remaining classic open-air bars in Key West. The Bull is on the ground level and the Whistle is on the second floor. Open from 10AM-4AM Monday-Saturday and 12PM-4AM on Sunday, the Bull offers great live entertainment on a regular basis. From comedy to classic rock, you can't beat the show at the Bull and Whistle.

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