The Conch Republic has their share of quirky celebrations that are an island tradition. Not sure whether you want to watch the shoe, conch, or pirate wench drop at midnight? Here’s some background on all our favorite Key West New Year’s Eve traditions to see which one suits you best.

New Year's Eve Sunset Cruise

Sail into 2022 in style. Fury has a few NYE options to choose from, with appetizers and live music to a simple Champagne sunset cruise. This is an island favorite to reflect on the past year and get ready for the new. Book in advance and see your options here.

Mallory Square Sunset Celebration

If you’d rather stick to land on NYE, Mallory Square’s final sunset celebration of the year seems to be the launch of all the island festivities. Join locals and tourists right before the sun goes down in Mallory Square to say goodbye to 2021 and hello to a night of festivities. Pop into El Meson de Pepe afterwards, the Cuban eatery will continue its “Cuban Cigar Drop” tradition come midnight.

New Year’s Fireworks

The island’s so small you’ll see the sky light up from anywhere, but if you want to get up close to the fireworks show, head to White Street Pier on the Key West Harbor side of the island. This is a good option for those who want to avoid crowds like those expected on Duval Street.

Conch Shell Drop at Sloppy Joe’s

A New Year’s Eve staple at a Key West institution. Watch the giant conch shell drop in front of Sloppy Joe’s. This is best if you aren’t shy in a crowd - it gets madly packed in front of Sloppy Joe’s before midnight.

Schooner Wharf Party & Lowering of the Pirate Wench

Schooner Wharf Bar throws a massive bash at their spot on Key West Bight every year. There’s live music, party favors, and more with no entry fee. At the stroke of midnight on New Year’s Eve, a pirate wench is lowered from the top of a ship down to the new year.

Watch the Shoe Drop with Sushi

In NYC’s Times Square, the ball drops; in Key West’s Duval Street, a giant high-heeled shoe drops - with a drag queen named Sushi inside. This KW tradition began in 1996 and has continued ever since. Read more about it here. Enjoy the tradition from the New Orleans House at 742 Duval Street. VIP balcony tickets are also available and always sell out. For more info, check out their website.

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Ready to ring in the new year with us? Book your rental for New Year’s Eve at The Gates Hotel to be close to the celebrations. See our specials.