The Five Biggest Festivals in the Keys

Fantasy Fest, Key West

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It’s always a good time to visit the Florida Keys. But if you happen to visit during one of the many memorable festivals, you’ll get even more out of your vacation. Check out some of the biggest festivals in the Keys and don’t miss out on any of the fun.

Conch Republic Independence Celebration

This festival celebrates the brief independence of the Florida Keys. In 1982, the U.S. Border Patrol placed a blockade on the Florida Keys. Unhappy with being treated like another country, the mayor of the keys seceded from the United States. For the brief duration of the secession, the Keys was known as the Conch Republic.

In memory of the secession, Key West hosts an annual independence day celebration. The festival features unique events, like a beachcomber hat contest, an art fair, and a beach clean-up. You can head into just about any bar for a special celebration or join in on a bar crawl. In the past, notable events have included a Drunken Spelling Bee, the World’s Longest Parade, and a Pirate’s Ball. Every year, there’s something new and exciting going on at the festival.

Hemingway Days

Although Ernest Hemingway is long gone, you can honor his memory at this iconic Keys festival. Once a year, Hemingway Days brings Hemingway fans to Key West. 

Ernest Hemingway lived in the Keys for almost all of the 1930s. While on the island, he spent much of his time writing. This festival honors his time and brings together people who still appreciate his literary masterpieces.

One of the major attractions of this festival is the Hemingway look-a-like contest. Stocky men with beards all gather together at one of Hemingway’s favorite old haunts, Sloppy Joe’s Bar. But you don’t need to look like the literary giant to enjoy yourself. Throughout the festival, there are several other unique events.

For instance, there’s a marlin tournament. Despite having a passion for writing, Hemingway also had a passion for fishing. There’s also a re-enactment of the running of the bulls. While it may not be as dangerous as the famous event from Spain, the re-enactment is just as fun.

There are also plenty of opportunities for spectators to enjoy Hemingway’s writing. Several local bars host readings and discussions of his literary work. Pull up a chair and listen in to rediscover his unique writing.

Fantasy Fest

A 10-day festival, Fantasy Fest is not for the faint of heart. It’s an adult party that first started in 1979. Locals kicked off the fun with a party that was designed to bring tourists to Key West. Although the town needs no help getting tourists these days, the festival is still going strong. 

Every October, people flock to Key West to celebrate this event. Fantasy is all about having fun and celebrating life, so there is plenty of creativity. People wear costumes, indulge in drinks, and party all day and night. 

During the first year of the event, there was a small parade featuring Halloween-inspired costumes. Over time, the parade has grown into a huge event showcasing some of the most unique costumes you’ve ever seen. Throughout the duration of one festival, there may be over 60 parties, balls, fairs, and marches. 

Every year, Fantasy Fest draws up to 75,000 attendees. People flock from all over to party for days on end. If you plan on attending, you should know that people plan their costumes and their accommodations far in advance.

Key West Lobsterfest

If you like seafood, you’ll love the Florida Keys. And can you think of a better way to celebrate local seafood than a festival? For 24 years, Key West has been celebrating its rich seafood cuisine with the Key West Lobsterfest.

The best way to describe this event is a summer party that tantalizes the tastebuds and embraces the Keys lifestyle. Over the course of several days, the event has fun events. One highlight is the lobster boil. In the past, the boil has featured fresh lobsters, jumbo shrimp, corn on the cob, and other Southern dishes. 

If you’d rather drink than eat, you might prefer a pub crawl. Make your way down Duval street and check out some of the hottest bars. The crawl goes on late into the evening, so be sure to plan for a long night of fun. 

For some more fun, you can attend the street fair. Check out items sold by local vendors or listen to live music. There are usually performances by popular local entertainers, which makes your shopping even more fun. You never know what souvenirs you’ll find at the fair.

If you get hungry, you can stop at any one of the local establishments and check out their lobster-inspired menus. Or, stop in for some drinks. The atmosphere is fun and relaxing.

The Key Lime Festival

When most people think of the Keys, they think of vacations, beaches, and parties. But there’s another thing that should come to mind – key limes. Every year, the Key Lime Festival celebrates the citrus and everything it has done for the area.

Much like the Keys, the Key Lime Festival is eccentric. It doesn’t just showcase the ways in which you can enjoy the fruit; it also highlights the unique culture of the area. Over a span of several days, visitors can attend multiple exciting events. While some of the events are culinary-focused, others are more about coming together and having fun.

For instance, the Key Lime Pie Hop is a popular event. Others enjoy the Key Lime Cocktail Sip and Stroll. While you enjoy a cocktail, check out the shops and boutiques on the main streets. The event organizers work hard to add new events to the roster every year. 

Participating in the Biggest Festivals in the Keys

Whether you decide to attend one of these festivals or you find your own, you’ll enjoy your time in Key West. There’s no place like it, and no place that has such unique festivals. See for yourself what it is that makes Key West such a special place.

For a full list of Florida Pride Festival, click here.

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