A Pirate Wench, the Iconic Red Shoe, and a Conch Shell Drop to Ring In the New Year

New Year’s Eve in Key West is anything but ordinary. As tropical breezes fill the air, the countdown to midnight unfolds with quirky island traditions and an energy you won’t find anywhere else. Picture a pirate wench descending from the mast of a tall ship, a sparkling red high heel dropping over Duval Street, and a glowing conch shell lighting up the crowd at Sloppy Joe’s. In Key West, saying goodbye to the old year is as unforgettable—and as unique—as the island itself.

Here’s your guide to the island’s can’t-miss celebrations.

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.

Staying at The Marker? Schooner Wharf Bar is just steps away—putting you right in the heart of all the action at the Seaport.

Live Music: Bands and DJs keep the party going all night.
Cost: Free.
Learn More: Schooner Wharf Bar

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.

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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 unforgettable live show at La Te Da Cabaret.

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. Photo credit: Carol Tedesco.

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 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.

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With live music, a rooftop host leading the countdown, and the legendary bar’s electric energy, this free event is a Key West classic that brings everyone together. Photo credit: Carol Tedesco.

If Hemingway were here, you’d likely find him raising a glass where he once drank, celebrating this iconic tradition with locals and visitors alike.

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.
Cost: Free.
Where: Sloppy Joe’s Bar, 201 Duval Street.

Recharge and refuel so you’re ready to ring in the new year—Key West style!

You can’t have the best New Year’s Eve experience on an empty stomach. Fuel up before you go with breakfast or lunch at our poolside restaurant and bar, where you’ll find a variety of menu options to satisfy every craving. From tacos, burgers, and pizza to other island favorites, it’s the perfect way to recharge before heading out for an unforgettable night and celebration.

As we say goodbye to 2024, we want to thank you for staying connected and sharing your memories with us. Here’s to a happy, healthy, and unforgettable new year. We can’t wait to welcome you back in 2025! #lovethemarker

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