How We Countdown to the New Year: Key West’s Quirky Traditions & Unforgettable Drops
New Year’s Eve in Key West is anything but ordinary. Thousands gather on the streets to welcome the new year together—whether it’s by the Seaport or on Duval Street, you’ll find island traditions unlike anywhere else. From a pirate wench descending the mast of a tall ship, to a sparkling red high heel dropping over Duval, to a glowing conch shell lowering to light up the crowd at Sloppy Joe’s Key West offers a celebration as quirky and unforgettable as the island itself.
Here’s your guide to the island’s can’t-miss celebrations.
The Red High Heel Drop on Duval Street
Glamorous, glitzy, and show-stopping—the Red High Heel Shoe Drop at Bourbon St. Pub is pure Key West flair. Legendary female impersonator and performer Randy Roberts, known for his spot-on impersonations of Bette Midler, Cher, and other iconic divas, takes center stage—perched inside a giant, sparkling red high heel. Photo credit: Carol Tedesco.
Did you know? Roberts isn’t just a local favorite—he’s also a former contestant on America’s Got Talent, where his electrifying performances wowed audiences nationwide. When in Key West, you can catch his live show at La Te Da Cabaret, just a couple of blocks from our Key West Beach Resort on Duval Street.
As the clock strikes midnight, thousands of revelers pack Duval Street, cheering and celebrating as the dazzling red high heel descends from the balcony—welcoming 2024 in true Key West style.
Bourbon St. Pub – Red High Heel Shoe Drop
Festivities: Kick off at 9 p.m. with live music and entertainment.
Where: Bourbon St. Pub, 724 Duval Street.
The Lowering of the Pirate Wench at Schooner Wharf Bar
At the Key West Historic Seaport, the Lowering of the Pirate Wench at Schooner Wharf Bar is a celebration that combines maritime charm with Key West’s love of spectacle.
As the clock strikes midnight, Evalena Worthington—Schooner Wharf’s iconic owner and pirate wench—makes a dramatic descent from the towering mast of the tall ship America 2.0. Accompanied by cannon fire, glowing countdown numbers, and cheers from the pirate-clad crew below, it’s a scene straight out of a sailor’s tall tale—and a beloved Key West New Year’s Eve tradition. Photo credit: Rob O’Neal
Live Music: Bands and DJs keep the party going all night.
Learn More: Schooner Wharf Bar
The Conch Shell Drop at Sloppy Joe’s
As thousands gather on Duval Street, all eyes turn to the roof of Sloppy Joe’s Bar, where a giant, illuminated conch shell—the symbol of the Florida Keys—slowly descends. The crowd cheering and counting down as the conch shell drops to mark the stroke of midnight.
With live music, a rooftop host leading the countdown, and the legendary bar’s electric energy, this free event is a Key West classic. Photo credit: Carol Tedesco.
And if Hemingway were here? You’d likely find him raising a glass in the very spot where he once drank, celebrating with locals and visitors alike. With a history dating back to the 1930s, Sloppy Joe’s is a Key West institution—and there’s no better place to celebrate like Hemingway might have.
Sloppy Joe’s – Conch Shell Drop
Live Music: Bands perform throughout the night, inside and out.
It’s the perfect blend of history, fun, and island energy.
Sloppy Joe’s Bar, 201 Duval Street.
Recharge Refuel Before the Countdown
You can’t have the best New Year’s Eve experience on an empty stomach. Enjoy a delicious breakfast, lunch, or dinner at Southernmost Beach Café, where Atlantic Ocean views meet island-inspired flavors. Prefer to take it easy? Relax poolside with a tropical drink in hand and recharge before heading out to ring in the new year—Key West style.
As we say goodbye to 2024 and welcome 2025, thank you for staying connected and sharing your memories with us. Wishing you a happy, healthy, and joyful new year. #somolife