New Year's Eve pirate wench "drop" Key West
  • "Pirate wench" Evalena Worthington prepares to welcome 2019 with her traditional New Year's Eve descent from the top of a tall ship's mast, dockside at the Schooner Wharf Bar. (Photo by Rob O'Neal, Florida Keys News Bureau)

     

  • By: Carol Shaughnessy
  • December 11, 2019

New Year’s Eve celebrations in the Florida Keys traditionally feature balmy temperatures and a warm welcome for revelers fleeing colder spots (you know who you are!). From beachside fireworks where overcoats and gloves aren’t allowed to wacky takeoffs on the traditional ball drop in New York’s Times Square, you’ll find a wealth of ways to welcome 2020 in the subtropical island chain.

Key West New Year's Eve Sushi

Drag queen Sushi entertains New Year’s Eve crowds before a past year’s “Red Shoe Drop” outside the Bourbon St. Pub on Duval Street. (Photo by Andy Newman, Florida Keys News Bureau)

For example, as midnight approaches Tuesday, Dec. 31, thousands of people are expected to ring in the New Year on Key West’s famed Duval Street by enjoying a quirky island tradition dubbed the “Red Shoe Drop.” Renowned female impersonator Sushi stars in the festivities, perched in a supersized red high heel shoe suspended high above the crowds at the Bourbon St. Pub/New Orleans House complex.

Just before midnight a dazzlingly gowned Sushi, riding in the glittering shoe, will be lowered from the balcony of the complex to the accompaniment of cheers from the crowd below. Live entertainment on a Duval Street stage will add a sophisticated spice — with performers including international recording artist Beth Sacks.

Down the street outside Sloppy Joe’s Bar (yes, Ernest Hemingway’s former hangout) the focus of frivolity is on a gigantic manmade conch shell — the symbol of the Florida Keys — during the annual “Dropping of the Conch Shell.” Events are emceed by a rooftop host and, as a huge clock counts down the seconds to midnight, the shell begins to descend from its supports to the flat roof of the legendary bar. (FYI, no reservations or tickets are needed for the popular outdoor event.)

In the Key West Historic Seaport outside the Schooner Wharf Bar, you can unleash your inner buccaneer. That’s because the watering hole stages an annual “Lowering of the Pirate Wench” each New Year’s Eve to celebrate the island’s colorful seafaring heritage. Just before midnight, the winsome wench begins her descent from atop the mast of the tall ship America 2.0 as cannons boom. The event includes live music and festivities at the Schooner Wharf.

In Key Largo, a New Year’s Eve fireworks extravaganza hosted by Sundowners will light up the sky above Blackwater Sound.

Or you might choose to greet 2020 by applauding a huge replica of a Key lime wedge splashing down into a larger-than-life margarita glass on the Sunset Pier at Ocean Key Resort & Spa. Or check out the “landing” of a flight attendant in a section of a replica aircraft at First Flight Island Restaurant & Brewery (whose historic building is known as the birthplace of Pan Am), or the offbeat “tuna drop” at the Smokin’ Tuna Saloon.

In the Middle Keys, Marathon’s gorgeous Isla Bella Beach Resort is planning dinner, dancing and celebration on New Year’s Eve. Options for fun include a gourmet buffet, live music, “endless bubbles” and champagne toasts.

Revelers in the sport fishing capital of Islamorada can welcome the new year with midnight fireworks on the beach at the luxurious Cheeca Lodge & Spa. Attractions include live music and dancing on the beach.

Also in Islamorada, consider ringing in the New Year with fireworks at midnight on the beach at Morada Bay Beach Cafe. The evening also features a large beach party with live music, a beach barbecue, cocktails and performers — all combining into a fabulous island experience.

And at the head of the Keys in Key Largo, a New Year’s Eve fireworks extravaganza will light up the sky above Blackwater Sound. The festivities, which include live music, are hosted by the terrific Sundowners.

One last suggestion: the events here are sure to be New Year’s Eve highlights in the Florida Keys, but additional celebrations are likely to spring up around the party-loving island chain. So stay up-to-the-minute on holiday happenings by clicking here.

 

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