Wondering what makes Key West the place to be on New Year’s Eve? Picture thousands gathering as the glittering red high-heeled shoe gets ready for its midnight drop, the glowing conch shell lights up the crowd at Sloppy Joe’s, and the pirate wench stands high on the mast of a tall ship at the Historic Seaport. When these iconic countdowns come alive, Key West turns into a celebration that flows from street to street and keeps the island buzzing long after midnight. Photo credit: Rob O’Neal.

The Red High-Heeled Shoe Drop

The famous red high-heeled shoe drop is one of the most recognizable New Year’s Eve traditions in Key West. Each year, a new queen takes her place inside the giant, glittering shoe outside Bourbon St. Pub on Duval Street. This year, Mulan Alexander steps into the spotlight, bringing her own style and energy to the celebration. Expect dancing and singing in the street, with festivities beginning well before midnight.

The Vibe: Fun, flamboyant, glitzy, and entertaining
From Southernmost: A five-minute stroll up Duval brings you directly into the heart of the celebration.

Photo credit: LARRY BLACKBURN/Keys Weekly

The Conch Shell Drop at Sloppy Joe’s Bar

At the corner of Duval and Greene, the illuminated conch shell sits on the rooftop of Sloppy Joe’s, ready for its slow descent at midnight. The street becomes one big block party as Key West gets ready to celebrate 2026, and for a moment, you realize you’re part of one of the island’s longest-running New Year’s Eve traditions. Get there early if you want a good spot.

The Vibe: Iconic, lively, classic Key West
From Southernmost: A fifteen-minute walk on Duval. Take your time and soak up the energy along the way.

Photo credit: Carol Tedesco / Key West Holiday Fest

The Lowering of the Pirate Wench at Schooner Wharf Bar

At the Historic Seaport, the island leans into its nautical soul. The annual Lowering of the Pirate Wench features Evalena Worthington descending from the towering mast of the tall ship America 2.0, docked in the Key West Bight in front of Schooner Wharf Bar. As midnight approaches, the crowd swells, the music rises, the cannon fires, and the countdown takes over the waterfront.

The Vibe: Nautical, offbeat, Old Key West
From Southernmost: A twenty to twenty-five minute walk brings you to the Historic Seaport and the Schooner Wharf celebration.

Photo credit: Rob O’Neal/Florida Keys News Bureau

How to Prepare for NYE in Key West

Start slow, soak up the sunshine, and let the day unfold at your own pace. New Year’s Eve at Southernmost is all about easing into the night ahead while enjoying our Key West beach resort.

Fuel Up

Fuel up for the big night poolside or at Southernmost Beach Café, where the Atlantic sets the tone and every table comes with a view. It’s the perfect spot to prep for the festive evening.

Hydrate Hydrate Hydrate

Drink plenty of water throughout the day to stay hydrated and ready for the long night of celebration. Later in the night, your future self will thank us.

Beach or Poolside Recharge

Spend the warm afternoon stretched out by one of our three pools, swaying in a hammock, or with your toes in the sand at the beach. 

The Southernmost Sunset Toast

Catch the final sunset of the year from our South Beach Pier. With a cocktail in hand, it is the perfect way to reflect on the year before stepping into the celebration.

Night Strategy: Dress and Timing

Wear comfortable shoes. Your outfit can sparkle, but Key West stays warm and you will be on your feet dancing in the streets with everyone else.

If you want a great viewing spot at any of the locations, plan to head out well before midnight. Two to three hours early is ideal and a great way to experience it all.

Have fun out there, soak in every moment, and let the night bring you the kind of memories that stay with you long after the New Year begins. Every New Year is a blank page. We hope you will be filling it with the people and experiences you love most. Happy 2026! #somolife