Key West, Florida is the southernmost point of the United States. You can also describe it as a small fishing town with a drinking problem. I will take you around the island for a long weekend of the best drinking you can have.
I would say that the best time to spend a long weekend in Key West is in the Springtime. Spring in Key West is Spring break season, and it creates a very fun experience. Key West is the birthplace of “It’s five o’clock somewhere,” so do not be afraid to go have a noontime drink, you will be welcomed not judged here. The best part about Key West bars is that once you go to a bar, it does not mean you cannot go back again. Your first day in Key West, you want to find the bars you like so that you know what to go back to. My advice is to have one drink at each bar, if you really like it there stay, but if you want to see the other ones, keep your pace.
If you are starting in the daytime, I say start at Jimmy Buffett’s Margaritaville. This is the original Margaritaville, so even if you are not a Buffett fan, it is still a sight to see. When at Margaritaville, start with a loaded Landshark. This is a Landshark, (Jimmy Buffett’s beer) filled to the top of the bottle with a shot of Margaritaville tequila, and a lime wedge. Now some people hear tequila and run but this does not have the taste of the tequila, just the effect. While enjoying your loaded Landshark, you can enjoy the scenery in Margaritaville, equipped with wall art of the founder Jimmy Buffett, live music, and a lot of tropical colors.
When in Key West, Captain Tony’s is a must stop. A dive bar off Duval street, is one of the original bars in the town. With a constant crowd and great drink specials, you can enjoy some more live music, a dance floor, pool tables and various undergarments hanging from the ceiling.
One of the local favorites is the classic Sloppy Joe’s. Opened in 1933 on the day after prohibition ended and has been a standard ever since. It is the most visted bar in Key West, and the selling point is that it was Hemingway’s favorite. Don’t expect anything fancy from this bar though, it is a simple place, but you are there to drink anyway.
There will be a lot of people at these bars because they are in prime real estate on Duval. So if you want to get a little bit of elbow room head off Duval one block to The Green Parrot. The Green Parrot is another simple drinking establishment with one big bar, rather than the common set up of multiple smaller bars. The Parrot is a hangout spot, for patrons to relax at for that break in the crowds.
For a little bit of a nicer look, Smoking Tuna is the place to go. Nothing too fancy, but not a dive, and a great place for some food. However, if you want some really great food with your drinks head to Schooner Warf, at the end of Duval. A place with constant live music and a great menu and bar, it is one of the best places on the island.
It is an understatement to call Key West a place with an alternate lifestyle. So if you are into some more unique experiences, you will find plenty of places. Duval street is lousy with diversity so just look up and you will find something. There are multiple gentleman’s bars, so if that is your thing you have that to go to. If you like something even more unique, there are a few bars that will offer a drag show. The most visited is probably Aqua Nightclub, or Bourbon St. Pub which is a men only bar, stated to be Key West’s best gay bar. There is also a place called Garden of Eden, which is a rooftop clothing optional bar. This means that some visitors go up to the roof and remove some clothing, so buyer beware. There are a lot of above middle aged men who like to, let us say, drink freely.
Other notable bars in Key West are Hog’s Breath Saloon, Irish Kevin’s (for the big time drinkers), Flying Monkey, and The Bull & Whistle. All these are similar type bars but a lot of fun nonetheless.
Key West is a town for your pleasure, but be careful, because it is very easy to both over spend, and over drink. Spread your bar trips out the days you are there, because remember, there will still be alcohol tomorrow. Enjoying Key West responsibly can be the best experience of your life, but you are more then likely to go a little crazy.