There is no place in America quite like Key West; a four-mile wide, two-mile long island located at the southernmost tip of the Florida Keys, it is almost like its own little country existing independent of mainland America. Known for the strong Latin (particularly Cuban) influence on its culture, its bohemian leanings, and its year-round 24/7 beach-party atmosphere, it is a popular celebrity vacation destination and has been (and still is) home to many notable public figures. Although it is a very small city both in population and physical size, it is regarded as one of the top nightlife destinations in the US, rivaling some of the largest metropolitan centers in the country.
If you enjoy a good classic bar rife with character and history, you will love the Key West bar scene. It is almost hard to believe that there could be so much ground to cover on such a small island when it comes to hitting all the relevant bars during one trip to the city. The Schooner Wharf Bar is one of these establishments, owned by boat enthusiasts who dock multiple classic boats on the water the bar directly overlooks. For good booze set to breathtaking waterfront sunset views, the Schooner is a favorite for locals and tourists alike. Hog’s Breath Saloon has been a Key West staple for over 30 years, known for hosting some of the most popular annual events in town, while Captain Tony’s Saloon, located at 428 Greene Street (the same address where the popular bar now known as Sloppy Joe’s was originally located from 1933-1937) is known as the oldest bar in Key West. If you grow tired of crowded and tourist-heavy Duval Street, take a jaunt over to Whitehead Street and pay a visit to the preeminent hangout for the grizzled local set, the legendary Green Parrot.
Due to the strong presence of the bar and restaurant industry in the city, there is a great need for live music, and this means Key West is home to some extremely talented local working musicians. Although there are not a lot of big-name touring acts coming through town, this is more than made up for by the rich local and regional scene. The aforementioned Sloppy Joe’s is a staple both as a bar and live music venue, open since 1937 at their current location at 201 Duval Street. Famous for being one of the late Ernest Hemingway’s favorite bars in his beloved Key West of old, they host live music from noon all the way until 2 AM every day. The Bull (located in the same building as the Whistle Bar and Garden of Eden) is a prominent Key West drinking establishment doubling as a seven-day-a-week live music venue. Jimmy Buffett’s flagship location of his Margaritaville bar and restaurant chain is another excellent spot to catch some Key West-flavored live music during your stay.
Key West is home to a large gay population and has long been known as a prominent gay tourist destination, which means that there is a thriving nightlife scene for the LGBT crowd in the city. When looking for gay nightlife, or any nightlife in Key West for that matter, most of it can be found on Duval St., the center of the Key West bar and club scene. Aqua Nightclub is the place to be for drag shows Tuesday through Sunday with late-night dancing to follow, and also features a popular karaoke night on Monday. Pearl’s Patio Bar For Women is the nightlife home to the the local lesbian community, while the previously referenced Garden Of Eden is a clothing-optional mixed gay/straight establishment. Every happening gay scene has a leather bar, and in Key West the buck stops at Saloon One. If you want to just chill out at a low-key mixed gay/straight neighborhood hangout spot, you might hit up Bobby’s Monkey Bar for a drink or two.
As you would expect from a freewheeling bohemian destination such as Key West, it is also home to some excellent gentlemen’s clubs. Bare Assets, rightfully calling itself “the southernmost strip club in the USA” is the largest strip joint in town and probably the best for large groups such as bachelor parties. The Red Garter Saloon inside Rick’s and Durty Harry’s entertainment complex is another popular Key West strip club, known for featuring exotic women from all over the world. Although there are not a lot to choose from, which is understandable considering Key West’s size, the old adage quality over quantity should apply when it comes to Key West strip clubs.
There is a reason why Key West is one of the top spring break locations in the US, and that is its world-class nightlife. A drinker’s paradise and a 21+ playground for the adventurous and fun-loving among us, Key West is a never never land of sorts where you can escape literally and figuratively from the everyday rigors of the mainland and truly let your hair down for a change. If you really want to let loose and embrace the night on your next vacation, we suggest you strongly consider Key West as your party destination of choice.