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The Running of the Bulls with during the Hemingway Days event.

The Top 2024 Key West Festivals You Won’t Want to Miss

A look at the conch-blowing contests, Hemingway lookalikes, and mind-blowing masquerades to frame a 2024 Key West vacation around.

(Feature image) © Andy Newman | Florida Keys News Bureau

For such a small island – sizing in at just 4.2 square miles – Key West sure knows how to go big when it comes to parties. That’s perhaps best demonstrated in the seemingly never-ending merry-go-round of annual eclectic Key West festivals that call this southernmost outpost home, from May’s Key West Songwriters Festival to October’s wild and zany (and clothing optional) Fantasy Fest. And with four Opals located in fun and funky town – Opal Key Resort & Marina, The Capitana Key West, The Laureate Key West, and Sunset Key Cottages – there are plenty of places to stay when you frame a visit around one of these top Key West festivals.

January 11–14, 2024

Best For: Serious readers who just wanna have fun

© Nick Doll

The Key West Literary Seminar is a four-day event that explores a unique literary theme each January, with presentations by some of the world’s most renowned writers – from big kahunas like Margaret Atwood and Jamaica Kincaid to fantasy writer Marlon James and young adult books legend Meg Cabot of Princess Diaries fame. This year – since the theme is “Florida: The State We’re In” – expect a roster that includes distinguished authors who know the Sunshine State better than anyone, like Carl Hiaasen, Dave Barry, and Jeff Vandermeer. The schedule is packed with keynotes, signings, readings, presentations, dinners, and film screenings, but since the main venue is right on Duval Street, you don’t have to choose between the literary life and Key West nightlife.

April 20–29, 2024

Best For: Sea dogs with Libertarian leanings

Some 30 years ago, in protest to a U.S. Border Patrol roadblock that shut down tourism, the then-mayor “seceded” Key West from the United States to become the Conch Republic – even declaring war on the US. Although a totally tongue-in-cheek demonstration (Major Dennis Wardlow was a bit of a joker) and a perfect example of Key West’s quirky spirit, the act was actually effective – the roadblock was immediately and quietly suspended. Not to mention, the “fifth world nation” stuck – today, complete with its own flag, passports, and this 10-day “independence” celebration, which kicks off with a conch-blowing contest and continues with boat races, a parade down Duval Street, victory parties, and the Pirate’s Ball and costume competition.

May 1–5, 2024

Best For: Those who like grooving on a Sunday afternoon – and Wednesday through Saturday, too

© Rob O’Neal | Florida Keys News Bureau

In the morning, it might be blues on the beach, then in the afternoon, powerhouse country rock in the Cuban cultural center. When you attend the Key West Songwriters Festival, the largest event of its kind in the world, you get to sample a wide spread of music genres thanks to 50 shows and 200-plus artist across some of Key West’s most famous indoor and outdoor venues, from watering holes to historic theatres. But remember, this is a festival dedicated to songwriting, meaning all the acts – which has featured the likes of platinum-selling recording artist Tyler Farr and CMT Award-winning Florida Georgia Line – do more than just perform their hits. They let you exclusively in on the little-known stories that inspired each and every tune.

July 17–20, 2024

Best For: English majors who are ready to come out of their shells

© Andy Newman | Florida Keys News Bureau

Honoring the legacy of the American literary giant who lived and wrote on the island during the 1930s, Hemingway Days is an annual event that is all about the old man and the sea. Yes, there’s the requisite feast of prose, poetry readings, and presentations by Hemingway scholars (in previous years, writer Cristen Hemingway Jaynes, the novelist’s great-granddaughter, made an appearance). But the bell that tolls loudest in festival-goers’ hearts is the lookalike contest, in which hundreds of white-bearded, cocktail-slinging Papa Hemingway doppelgangers ham it up for the crowd (think of it like a beauty contest for old men), then take to Duval Street for a mock bull run.

August 29–September 2, 2024

Best For: Those who like to pair their surf with suds

Whether you’re a brewmeister with a finely honed palate or you simply love to kick back with a cold one, you can sample more than 200 beers from 60 vendors – both locally, nationally, and worldwide – at the pairing dinners, brunches, seminars, happy hours, pool parties, and late-night after-parties at the Key West Brewfest. The Signature Tasting Event, held on South Beach just below the famous Southernmost marker, features the latest craft-erpieces from acclaimed breweries like Lagunitas, Terrapin Beer Company, Dogfish Head, and many more.

October 18–27, 2024

Best For: Those who love Halloween…and aren’t offended by a little nudity

© Carol Tedesco

October used to be a quiet time in Key West…until Fantasy Fest sprung up in a cloud of glitter and feathers. Back in 1979, a few local business owners decided to drum up some action with an event that riffed on the only other party-friendly day of the month: Halloween. That first small but outrageous costumed march down Duval Street has now grown into 10 days of parades, street fairs, and glamorous balls – drawing some 75,000 visitors annually. There’s a different theme each year – from “Freaks, Geeks, and Goddesses” to the plays of Tennessee Williams – and opportunities galore to strut your stuff, including the Masquerade March and the Fantasy Fest Parade. With the exception of the Goombay Festival (see next highlight), a lot of these activities aren’t for kids – the full schedule of “Little Black Book” events include “naughty” bike rides, pajama parties, burlesque shows, and the famous Fantasy Fest Kink Party. Think of it as the embodiment – with lots of skin showing – of Key West’s official motto: “One Human Family.”

October 2024 (Exact date still to come)

Best For: Those who are looking for a more family-friendly fest

A festival within a festival, the two-day Goombay Festival is Fantasy Fest’s core family-friendly offering that celebrates Key West’s Bahamian heritage with Caribbean food, arts, crafts, dancing, face painting, carnival rides, and parades. Goombay is a form of Bahamian music (it’s also the name of a goatskin drum), and the festival is filled with rhythm – gospel, reggae, calypso, soca, hip-hop, and more, all performed live – as well as the Junkanoo Rush, a traditional Bahamanian celebration with costumed marchers and dancers. The events are centered around the island’s historic Bahama Village, a 16-block neighborhood just a short walk from Old Town, where you’ll find classic Florida Conch architecture in sherbet shades, and a plethora of great restaurants and shops.

November 26–December 25, 2024

Best For: Those who love the holiday trappings, but are not dreaming of a white Christmas

© Rob O’Neal

Swap out the snow for sand, the eggnog for a margarita, and make your slice of pie that of key lime. In the month before Christmas, Key West’s Bight (a bend in the shoreline on the northwest side of the island that creates a naturally protected harbor, from Green Street to the Ferry Terminal) hosts an expansive series of holiday events, including the lighting of three Christmas trees – one made with fishing buoys, another with lobster traps, and a nautically themed pine tree – the Classic Car Show, and holiday concerts. But none is more anticipated than the Lighted Boat Parade, which takes the glow to another level by giving entrants plenty of incentive to go big or go home with more $20,000 in prizes. Expect brilliant displays of holiday lights, conch shells, gingerbread men, jumping dolphins, and even a few Grinches.

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