The Florida Keys are a pretty unique place. The chain of islands feature tropical weather and a rich history, which has blended into a special brand of kitsch, and the very best place to experience it all is the Southernmost island: Key West. Presidents and authors have called Key West home, but the city is better known for its "Key" lime pie and its association with Jimmy Buffet's song Margaritaville. It might be hard to avoid some of the cheesy, touristy attractions, so you might as well embrace it while you're here. You're on vacation, after all!
Key West is as close to Cuba as you can get without leaving the country (it's only about 90 miles away!). Pay tribute to our neighbors with a traditional Cuban meal at El Siboney, a hidden gem of a restaurant. From Cuban sandwiches to churrasco, everything they make is authentic and delicious. Finish off the meal with a cold beer, or some housemade sangria, and enjoy yourself!
Key West has a really unique history, and you can really delve into it at the Fort East Martello Museum. It's got a little bit about everything, from sponge-diving and cigar-making to naval defense and shipwrecks. But the main attraction here is Robert the Haunted Doll, which is the real-life inspiration for Chucky from "Child's Play." Robert was donated to the Fort East Martello Museum where he allegedly terrorizes the staff and visiting guests. Things got so bad at one point that Robert’s case was moved away from the other displays because he kept knocking them over. According to eye-witnesses, Robert is also a fan of giggling, knocking over objects, and changing expressions, which he is known to do quite often.
Now that you've gotten a good sense for Key West (and it's weird side), head to the former home of one of the people it inspired the most, prolific American author Ernest Hemingway. He lived in the house on Whitehead Street from 1931-1939, and wrote several important works while living here. Beyond that, the Ernest Hemingway Home and Museum is a beautiful house-turned-museum, plus, it's home to six- and seven-toed cats that are descended from the original pets Hemingway kept here.
Dinner with ocean views? Sounds perfect. Turtle Kraals is located on the water and has a great rooftop bar, awesome fresh ceviche, bocce ball courts, and live music, but they're probably best known for their thrice-weekly turtle races. Place bets on which critter you think will be first to the finish line, and you might even win a prize. Definitely a fun after-dinner activity!
Ernest Hemingway, Truman Capote, Shel Silverstein, Tennessee Williams and the Mayor of Margaritaville himself, Jimmy Buffet, have all enjoyed a drink (or 10) at Captain Tony's Saloon in Key West, Florida. What the tourist guide books often fail to note is the fact that the dive bar used to be a morgue. In fact, there are still bodies buried underneath the bar stools.
At the turn of the century, the building was used as a cigar factory and then as a speakeasy, where men and women gambled and cavorted, fast and loose. It was eventually bought by the notorious Captain Tony, a fishing boat captain, gunrunner, gambler, and Key West celeb. Today, it's one of Key West's most iconic and divey-est beach bars.
Hog's Breath Saloon is another great dive bar, albeit one with more of a Western vibe. Hog's Breath features fruity, tropical drinks, live music, dancing, and a fun crowd, making it a good place to really get into vacation mode.
When you're ready to hit the hay, the Artist House is one of the most charming B&Bs in all of Key West. Located in an old Victorian home that's been impeccably kept-up and that is within walking distance of Duval Street, the character is only improved by the gracious hosts. Pro tip: ask for a room in the turret, and make sure to check out the adorable backyard space.
Floridian-Caribbean cuisine makes Blue Heaven a must-try restaurant in Key West, and brunch is a great way to sample the flavors and enjoy the funky vibes. Egg Benedict with key lime hollandaise, Florida-fresh shrimp over cheese grits, and pineapple pancakes are all winners here.
Originally built in 1825, the Key West lighthouse offers an interesting slice of Key West history through the museum it now houses, as well as great views of the ocean. Make sure to learn all about Barbara Mabrity, one of the first female lighthouse keepers ever, who manned the light through hurricanes and storms before being fired for being too pro-Confederacy.
Step back in time at the Shipwreck Historeum, where you'll learn that the only thing more dangerous than being on a sinking ship is trying to salvage its wreck. The Shipwreck Historeum is an immersive experience that tells the tales of the ships that have sunk on the reefs off Key West, and the stories of those who have tried to rescue booty from the ruins!
There's more to Florida than just seafood, and Charlie Mac's is proof. This barbecue eatery serves up smoky, saucy meats, cold beer, and mouth-watering sides to tourists. Sample as many of their homemade sauces as you can: they're all delicious in their own, unique ways.
The historic home that now houses the Harry S. Truman Little White House Museum, which is part of the naval station, has played host to Thomas Edison, JFK, Dwight Eisenhower, Bill and Hillary Clinton, Jimmy Carter, and William Howard Taft, but it's best known for being the winter White House for President Harry S. Truman. He took frequent trips to Key West and spent nearly 200 days of his presidency here. Take a guided tour of the museum for special insight into the important events that took place here.
You didn't officially take a trip to Key West without a picture at the Southernmost Point. The tip of Key West was once marked by a sign, but after it was repeatedly stolen, the city decided to make a concrete buoy to mark the spot... even though the technical southernmost point is on US Navy property and can't be accessed by civilians.
Make sure to nab a reservation at Nine One Five on Duval Street. This classy joint will help you enjoy Key West in style. Dishes like chicken liver terrine pate, gravlax, beef carpaccio, and ossobuco are complemented perfectly by Nine One Five's massive selection of wines, and it's all best enjoyed on the patio.
Hemingway frequented Sloppy Joe's bar in the 1930's, when it was located where Captain Tony's now resides. In fact, they claim that Hemingway was the one who coined the name "Sloppy Joe's." It also gets a shout out in the movie "Citizen Kane." Today, they still serve up live music and frozen rum-laced drinks to tourists looking to have a good time, Hemingway-style.
Another historic Key West dive, the Green Parrot has been boozing up its patrons since 1890. This is more of a local joint, with strong, cheap drinks, rocking live music, and a lower-key crowd.
The best time of year for a 48 hour adventure in Key West: Summers here are rainy and humid, but often less crowded than winter, when the weather is a lovely 70-80 degrees and prices for hotels rise. Late summer and early fall bring hurricanes, and, similarly, spring brings wild spring breakers, so be aware.