Let’s be honest: the Florida Keys don’t need an excuse to throw a party. It’s pretty much their default setting. But if you give them an actual reason—like a historic rebellion, a beloved dessert, or just a Tuesday—they will absolutely turn it into a full-blown festival.

Planning a trip to the Keys? It’s a good idea to know what’s happening and when. Not only can you join in on the fun, but it also helps you prepare for the realities of visiting during a major event. Think: higher hotel prices, more people on Duval Street, and a general increase in happy chaos. On the flip side, planning around the festival calendar means you could stumble upon your new favorite annual event.

So, grab your calendar and a cocktail, because we’re about to walk through the year-round party scene in the Florida Keys. From live music to wacky parades, here’s what you won’t want to miss.

January: Kick Off the Year with Live Music

You’d think after the holiday madness of December, they would take a little break. Nope. January rolls in with the Mile Zero Music Festival, a multi-day annual rock n’ roll event that turns Key West into a giant concert venue.

This festival brings in a mix of Red Dirt and Americana bands, drawing music lovers from all over. You’ll find performances happening on the main stage at the Truman Waterfront Park Amphitheater, but don’t sleep on the smaller, more intimate shows at some of the Keys’ best local spots and bars. It’s a fantastic way to discover new favorites and enjoy incredible live performances in a laid-back island setting. It’s the perfect cure for the post-holiday blues.

February: Presidents, Pups, and Pirates

February in the Keys is eclectic, to say the least. For the history buffs, there’s the Presidential Families Weekend at the Little White House, where Harry S. Truman used to escape the winter chill. It’s a cool, geeky dive into a unique piece of American history, right in the heart of Key West.

But because this is Key West, we also have… a Pup Crawl. Yes, a parade for you and your four-legged best friend. It’s as adorable and chaotic as it sounds. Then there’s the Schooner Wharf Wreckers Cup Race, a ridiculously fun event where modern-day “wreckers” race through the harbor, navigating obstacles to “rescue” goods. It’s a nod to Key West’s wild maritime past and a great excuse to drink rum on a Sunday.

March: Orchids, Seafood, and Tennessee Williams

March is a feast for the senses. The Orchid Festival at the West Martello Fort is a must-see, even if you don’t have a green thumb. The sheer variety and beauty of the orchids people cultivate here are just staggering. It’s a moment of zen before the next party.

Speaking of parties, foodies should head up to Marathon for the annual Florida Keys Seafood Festival. Think mountains of Key West pink shrimp, grilled fish, and every other kind of incredible seafood you can imagine, all caught locally. It’s a family-friendly event with food vendors, live music, and a real community vibe.

Back in Key West, March is also Tennessee Williams’ birthday month. The town celebrates one of its most famous literary residents with theater productions, readings, and film screenings. It’s a more cultured affair, proving they have a sophisticated side… somewhere.

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April: We Seceded, You See…

April is when our quirky, rebellious spirit truly shines. It’s time for the Conch Republic Independence Celebration, an annual 10-day party commemorating the day in 1982 when they jokingly (???) seceded from the Continental United States.

The festivities are pure Key West. There’s the infamous “drag race” (not what you think—it’s people racing in drag), a bed race down Duval, and the epic sea battle in the harbor. Watch as “Conch Republic” ships defend the waters from the “U.S. Border Patrol” with water cannons, stale Cuban bread, and toilet paper. It’s absurd, hilarious, and an absolute must-do. You haven’t lived until you’ve seen a grown man in a pirate hat launching a soggy loaf of bread at a Coast Guard boat.

July: A Salute to Our True King, Key Lime

July in the Keys is hot. Like, melt-your-sandals hot. But they have the perfect antidote: the annual Key Lime Festival. This is a multi-day culinary celebration dedicated to our most famous export. It’s a sweet, tart, and slightly tipsy tribute to the pie that put us on the map.

The festival features everything from a Key lime pie hop (a tour of the best restaurants and their pie creations) to a pie-eating contest. But the real star is the Key Lime Cocktail Sip & Stroll, where you can sample dozens of creative lime-infused concoctions. You’ll find everything from classic margaritas to martinis with a citrus twist. It’s the perfect place to indulge your sweet tooth and discover unique flavors. Fun fact: you’re at the birthplace of Key Lime Pie, so you’re getting the real deal.

Don’t forget the 4th of July festivities up and down the Overseas Highway, and for something truly unique, check out the Lower Keys Underwater Music Festival. Yes, it’s exactly what it sounds like: a dance party for divers and snorkelers set to an underwater playlist. Only in the Keys, folks.

Want the full calendar of events? Check it out here

October: The Reign of Fantasy Fest

October is not for the faint of heart. This is the month of Fantasy Fest, the biggest, wildest, and most famous 10-day celebration. What started as a small local party has exploded into an internationally known event that draws fun-loving revelers from all over the world.

Each year has an official theme (like 2023’s “Uniforms & Unicorns: 200 Years of Weird”), and the creativity is off the charts. The festival kicks off with the exuberant Goombay Festival, a Bahamian-style street party in the historic Bahama Village neighborhood. From there, it’s a whirlwind of parties, parades, and costume contests.

Highlights include:

• Zombie Bike Ride: Thousands of zombies on bikes take over the streets. The pre-ride party is almost as fun as the ride itself.
• Pet Masquerade: The enchanting Key West Pet Masquerade lets four-legged friends get in on the costume action. It’s surprisingly competitive and utterly adorable.
• Captain Morgan Masquerade March: This is the locals’ favorite parade, winding through the streets and stopping at guesthouses for free cocktails.
• Headdress Ball: The Annual Headdress Ball Pageant is a dazzling spectacle of creativity, where contestants show off massive, elaborate headdresses for cash prizes.
• The Grand Parade: The climax of it all is the Key West Fantasy Fest Parade, a massive procession of floats, dancers, and people in the most spectacular costumes you’ve ever seen. Expect lots of glitter, feathers, and body painting.

Fantasy Fest is the best party in town, but it’s definitely an adults-only affair.

November: Fast Boats and Fine Film

The party doesn’t stop after Fantasy Fest. November brings a different kind of energy with the Race World Offshore Key West Championships. Powerboats rip through the harbor at mind-boggling speeds, and you can catch the action from spots like Mallory Square or the Outer Mole. The parade of boats down Duval Street is a sight to behold.

For a change of pace, the Key West Film Festival takes over the town. Named one of the top film festivals in the country, it’s a fantastic showcase of independent cinema. You might just discover the next big director or see a future Oscar contender before anyone else.

December: A Very Island Holiday

As the rest of the country bundles up, Key West is decking the palms with twinkle lights. December in Key West is pure magic. The season kicks off with the Key West Hometown Parade, a charmingly local affair that feels straight out of a small-town holiday movie.

The real showstopper is the Schooner Wharf Lighted Boat Parade. Dozens of boats, from tiny dinghies to majestic schooners, get decked out in elaborate light displays and parade through the historic seaport. It’s a beautiful and uniquely “Keys” tradition.

And of course, there’s New Year’s Eve. Forget the ball drop in Times Square. They have three drops: the lowering of the giant conch shell at Sloppy Joe’s, the pirate wench at Schooner Wharf, and the drop of the drag queen in a giant red high-heel on Duval Street. It’s the perfect, quirky end to a year of festivities.

Your Festival Adventure Awaits

From the roar of powerboats to the sweet tang of key lime pie, there’s always something to celebrate in the Florida Keys. Each festival offers a unique opportunity to experience the culture, creativity, and slightly unhinged spirit of our islands.

So, whether you’re planning your trip around the Key West Songwriters Festival in May or the wacky Conch Republic Independence Celebration in April, you’re in for a treat. Just remember to pack your sense of adventure (and maybe some glitter). The Keys are waiting to show you a good time.