Before Fantasy Fest, Halloween was a sleepy, uneventful day in Key West. These days, it’s the busiest, most adrenaline and glitter-soaked day of the year. And that’s saying a lot, because on any day Key West is Party Central, where boredom goes to die and every day sees sunshine. Surf, sand, and a drink in hand is all you really need here, but you’ll get a lot more than that at Fantasy Fest, a parade-packed blowout with thousands of dollars in prize money up for grabs, and a healthy mix of “naughty,” “nice,” and just-plain-outrageous costumes.
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What to Expect at the Fest
This year’s theme is “Superheroes, Villains, and Beyond!” (Heavy on the “Beyond”) View the whole schedule, or peruse these crowd-pleasing highlights:
- Indecent Exposure: Are you comfortable in your Birthday Suit? Party with other likeminded souls in the Garden of Eden, a rooftop bar where clothes are optional. (Daily)
- Battle of Bone Island: Move over Star Wars. May the Force be with Key West’s burlesque stars, battling good and evil in this revealing revue. (Oct 19 — 22)
- Wake Green Party: Wear green and enjoy live Irish music for free. (Oct 22)
- Pet Masquerade and Parade: Dogs in costumes. Need we say more? (Oct 23)
- Blackout Glow Party: Head over to Coyote Ugly on Duval for some black light revelry and body painting. (Oct 24)
- Pretenders in Paradise: The most famous of all Fantasy Fest costume contests, and the most rewarding, with a prize of $10,000. (Oct 24)
- Street Fair: A nice hodgepodge of art, craft and food vendors. (Oct 25)
- 801 Bourbon Bar Tea Dance: Strut your best dance moves down DJ-lined Duval Street. (Oct 25)
- Southernmost Superhero Costume Contest: Show off your superhero garb at this poolside costume contest. (Oct 25)
- Fantasy Fest Parade: This year’s official parade is sponsored by Captain Morgan; appropriate. (Oct 26)
- The Fat Lady Sings Tea Dance: A DJ will be spinning tracks at the last official Fantasy Fest event. (Oct 27)
Festival Parking
Finding a parking spot in Key West is a real pain in the muffler. And that’s on a slow day. With all the revelry spilling out onto the streets during Fantasy Fest, make sure to plan your arrival.
- 24-hour parking is available at the corner of Caroline Street and Margaret Street, as well as Front Street and Wall Street. Rates range from $2 to $4 an hour, with daily maxes.
- At Grinnell and Caroline Street, you can “park and ride” for $2 an hour (the daily max is $13).
- No rental car? Don’t forget about the Key West City Bus! Also, bikes, scooters, and your own two feet are a great, hassle-free way to get around the fest.
Additional Excuses to Party
If the sanctioned Fantasy Fest debauchery just isn’t enough, you’ll find plenty more reasons to celebrate:
- Sunset Celebration: Two hours before sunset, swarms of people gather at Mallory Square to check out cool art, nibble on street food, and ooh and ah at jugglers and eventually, the setting sun. (400 Wall St)
- Hog’s Breath Saloon: Sip some local brews at this 25-year-old hot spot. (400 Front St)
- Hogfish Bar & Grill: Escape the chaos of Fantasy Fest for a more laid-back drink (or dinner) at this waterfront bar. (6810 Front St)
- Sloppy Joe’s: A once favorite hangout spot of Ernest Hemingway, today Sloppy Joe’s offers up a well-rounded menu and lots of live entertainment. (201 Duval St)
- Cigar Alley: Wine, beer, and cigars. A trio made in heaven? (Suite C4, 1075 Duval St)
Wind Down with Mother Nature
In between the parades, parties, and high jinks, squeeze in some quality time with Good Old Mother Nature. After all, you are on an island bursting with turquoise waters, dive-worthy coral reefs, and year-round sunshine.
- Key West Butterfly Conservatory: Flowers, waterfalls, and butterflies”¦ great place to nurse a hangover, huh? (1316 Duval St)
- Vandenberg Wreck: The second-largest ship to ever sink is on beautiful display, but only for scuba divers. (Near Mallory Square)
- Dolphins Plus: Swim with dolphins and sea lions. (31 Corinne Pl)
- Key West Aquarium: See alligators, jellyfish and other marine life up close. You can also feed sharks! (1 Whitehead St)
Never Too Old to Learn
Get to know “Old Florida”:
- Ghosts and Legends of Key West: Journey through Old Town and get the spooky scoop on the haunted Victorian mansions, voodoo lore, and other eerie and tall tales of Key West.
- Ernest Hemingway Home and Museum: For over a decade, Ernest Hemingway lived and wrote in this stunning mansion. (907 Whitehead St)
- Harry S Truman Little White House: Presidents can be snow birds, too. President Truman used to hide out here in the wintertime, but today it’s an impressive museum where government leaders still do business from time to time. (111 Front St)
- Shipwreck Museum: Don’t have any scuba diving skills? That’s alright. You can still see a shipwreck up close: the Isaac Allerton, which sunk in 1856. (1 Whitehead St)
Ernest Hemingway Home and Museum © Mike Richard
Drink Up + Chow Down
Before you get to drinking, make sure your stomach has a fighting chance. Thankfully, Key West is home to some unforgettable cuisine:
- Garbo’s Grill: Most food trucks are a one-note band, but this one has tacos, burritos, quesadillas, burgers, and hot dogs. Try the “Famous Cayo Fish” tacos, with grilled mahi mahi, jalapeno, and cilantro. (603 Greene St)
- Better Than Sex Dessert Restaurant: It’s hard to feel all that sophisticated while gorging yourself with cheesecake and fondue, but here you just might. Chocolate-rimmed wine glasses, and masterpieces like “Chocolate Grilled Cheese” and the “Tongue Bath Truffle” are as fancy as they are tasty. (926 Simonton St)
- Nine One Five: A Victorian home in Old Town is the setting of this award-winning restaurant, boasting entrees like “Pan Roasted Grouper” and “Crispy Whole Yellowtail Snapper.” (915 Duval Street)
- El Siboney: Cuban food cannot be missed when visiting the Keys, and there’s no better place to get your fix than here. (900 Catherine St)
Get Your Shop On
Tune out the tacky t-shirt shops and instead, spice it up, satisfy that sweet tooth, and marvel at ancient art:
- Peppers of Key West: Fall in love with the unique art of hot sauce tasting. (602 Greene St)
- Key Lime-N-More: Perhaps an online review says it best: “no words can describe.” We can try, though. This place is a pie paradise. The Key Lime ice cream and coffee aren’t too shabby, either. (424 Greene St)
- Archeo Gallery: Everything you can buy here is hand-selected and hand-crafted and”¦ old. The African, tribal, and ancient art and furniture here make this shop a living museum. (1208 Duval St)
Where to Stay
Key West vacation homes and Key West B&Bs are a much savvier choice than hotels. Spacious vacation rentals with multiple bedrooms, private hot tubs, ocean views, and full kitchens are often the same price as teeny tiny hotel rooms with parking lot views, microwaves and ironing boards. Plus, if you’re planning a girl’s or guy’s getaway for Fantasy Fest, everyone in your group can help split the bill of a roomy, luxurious, and charming accommodation, instead of booking multiple hotel rooms.