To put it mildly, Key West knows how to have a good time. New Year’s Eve is a big deal on the island, and 2024 will be no exception! As with every year, we’re looking forward to the all-out celebrations and festivities, and New Year’s Eve events across the Key include a number of parties and midnight drops to choose from. All are very much in-line with the island’s eclectic personality and anything-goes attitude. Here are the best New Year’s Eve parties in Key West in 2023.

[Holiday Events in Key West 2023]

Key West New Year’s Eve Fireworks Show on the Sunset Green Event Lawn

Get into the party spirit and build up to the big day with a special fireworks event on the Sunset Green Event Lawn at The Gates Hotel on Dec. 30. There will be delicious food and drinks, spectacular fireworks lighting up the night sky, and live music by The Marshall Morlock Band that’ll have you rocking on into the night. All ages are welcome. The Sunset Green Event Lawn opens at 6 p.m., fireworks at 9 p.m.

Stay just steps from this epic party when you book a room with The Gates Hotel. Our accommodations in Key West are inviting, comfortable, and close to all the best of the island.

New Year’s Eve Drag Queen Show

It’s the next day, and you want to keep the celebrations going. Begin New Year’s Eve at the Illusions Drag Queen Show on Petronia Street in Old Town. The 1:30 p.m. show is the perfect combination of burlesque and comedy, with the industry’s best celebrity impersonators and drag queen hosts. This event is 21+ and alcohol is available.

No Rest, in Key West: New Year’s Eve All-Day Happy Hour on Rooster Row

The island neighborhood that hugs Key West’s northeast corner is hosting an all-day Happy Hour on New Year’s Eve. Rooster Row has plenty of bars and restaurants to indulge in mouthwatering cocktails and island-inspired dishes. Best of all, they’re all within walking distance from your hotel room. All-day Happy Hour participants include Barefoot Bar & Brew (12 - 2 p.m.), Toasted Coconut (2 - 4 p.m.), Rum Row here at The Gates Hotel (4 - 6 p.m.), and Salty Lime (6 - 8 p.m.).

New Year’s Eve Party at RockHouseLive

Visit RockHouseLive across the street from Sloppy Joe’s at 135 Duval (more on Sloppy Joe’s NYE party below). The bar and venue is hosting its own New Year’s Eve party beginning at 6 p.m. The all-night rager goes until 4 a.m., with VIP balcony seating available for a spectacular view of Duval Street on the craziest night of the year.

Great Gatsby New Year’s Eve Party at First Flight Island Restaurant & Brewery

Dress in your best Gatsby-esque attire and hang with the crew at First Flight for one of the most happening parties on the island. A ticket to the event includes a full open bar, hors d'oeuvres, chef-manned action stations, live music, and DJ performances. At midnight, join in the Champagne toast while you watch an old Pan American Plane replica take flight in the garden surrounded by costumed party-goers. The party starts at 8 p.m.

As far as “drops” go, get ready to countdown to the New Year with Key West’s most creative, weird, and wacky New Year’s Eve drops:

Red Shoe Drop at Bourbon St. Pub

The Red Shoe Drop stars a local drag queen celebrity (beloved performer Sushi “dropped” for 25 years but retired in 2023!). Every year Sushi designed her own over-the-top dress to be revealed to the crowd during the big event at Bourbon St. Pub. She then was lowered in a giant red high-heel shoe from the balcony house at midnight. Stake out your spot ahead of time to watch the new queen descend above Duval Street.

Cuban Cigar Drop at El Meson de Pepe

Next to Mallory Square, El Meson de Pepe hosts its own version of the New Year’s Eve drop, albeit with an oversized Cuban cigar. This is an excellent spot to stick around on New Year’s Eve. The last sunset celebration in the square is sure to be enormous, plus El Meson de Pepe’s authentic Cuban fare and mojitos is a great way to spend the night before the countdown.

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Lowering of the Pirate Wench at Schooner Wharf

This one comes with a cannon boom to ring in the New Year! See the Tall Ship America 2.0 and count down to the pirate wench’s descent at midnight, all with live music and plenty of revelry at popular oceanfront bar Schooner’s Wharf. It’s considered more tame than any of the ‘drops’ you’ll find on Duval Street.

Conch Shell Drop at Sloppy Joe’s

Drawing the largest crowd in Key West, anything goes during what will now be the 30th edition of Sloppy Joe’s Conch Shell Drop. The idea came from Tobias McGregor, a Key West artist who proposed it to management after noting a lack of celebration at midnight along Duval Street. For live music entertainment, Justin Angelo takes the stage at noon, followed by Mojito at 5:30 p.m. and The Way Outs at 10 p.m. The bar’s rooftop show begins at 10 p.m. and when the clock strikes midnight, it’s an extravaganza of streamers, confetti, and lights.

If you’re visiting with kids or if wild parties aren’t your thing, consider staying on the harbor side and enjoying a sunset dinner; or even a sunset cruise. Key West has something for everyone! And if your New Year’s vacation is yet to be planned, take a look at The Gates Hotel’s special offers to book your stay today.