For such a small island – sizing in at just eight square miles – Key West sure knows how to go big when it comes to parties. That’s perhaps best demonstrated in the never-ending merry-go-round of eclectic annual festivals that call this southernmost outpost home. Here’s a look at the upcoming conch-blowing contests, Hemingway look-alikes, and mind-blowing masquerades to frame a future visit around.

Key West Fantasy Fest

© Michael Freas

Fantasy Fest, 10/20–27, 2019

For: Those Who Love Halloween…And Aren’t Offended by a Little Nudity

That first small but outrageous costumed march down Duval Street in 1979 has now grown into a week 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 opposite page), a lot of these activities aren’t for kids – the full schedule of “Little Black Book” events includes zombie bike rides, pajama parties, burlesque shows, and the famous Fantasy Fest Kinky Karnival Party. Think of it as the embodiment – with lots of skin showing – of Key West’s official motto: “One Human Family.”

Goombay Festival, 10/18–19, 2019

For: Those 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.

The Bight Before Christmas

© Rob O’Neal

The “Bight” Before Christmas, 11/20–12/25, 2019

For: Those Who Love Holiday Trappings, But Aren’t Dreaming of a White Christmas

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 Greene 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 than $20,000 in prizes. Expect brilliant displays of holiday lights, conch shells, gingerbread men, jumping dolphins, and even a few Grinches.

The Key West Literary Seminar, 1/9–12, 2020

For: Serious Readers Who Just Wanna Have Fun

This four-day event 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-book legend Meg Cabot of Princess Diaries fame. 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. Jump on this one fast – the January 2019 event sold out several months in advance.

Conch Republic Independence Celebration

Conch Republic Independence Celebration, 4/19–4/27, 2020

For: Sea Dogs with Libertarian Learnings

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, Key West features 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.

The Key West Songwriters Festival, 5/5–10, 2020

For: Those Who Like Grooving on a Sunday Afternoon…And Wednesday through Saturday, Too

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 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 artists across some of Key West’s most famous indoor and outdoor venues, from watering holes to historic theaters. But remember, this is a festival dedicated to songwriting, meaning all the acts – which, in 2018, included 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 in on the little-known events that inspired each and every tune.

Hemingway Days

© Andy Newman, Florida Keys News Bureau

Hemingway Days, 7/17–20, 2020

For: English Majors Who Are Ready to Come Out of their Shells

Honoring the legacy of the American literary giant who lived and wrote on the island during the 1930s, this annual event 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 2018, writer Cristen Hemingway Jaynes, the novelist’s great-granddaughter, made an appearance). But the bell that tolls loudest in festival-goers’ hearts is the look-alike contest, in which hundreds of white-bearded, cocktail-slinging Papa Hemingway doppelgängers 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.

Key West Brewfest, Late August (2020 dates still to be determined)

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 local, national, and worldwide – at pairing dinners, brunches, seminars, happy hours, pool parties, and late-night after-parties. 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.

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