Key West New Year’s Eve to Feature Offbeat ‘Drops’ in Subtropical Setting

KEY WEST, Florida Keys — New Year's Eve celebrations in the continental United States' southernmost island city traditionally feature balmy temperatures and a warm welcome for revelers fleeing colder climes. Chief among Key West's festivities are mutliple offbeat takeoffs on the traditional "ball drop" in New York's Times Square. 

As midnight approaches Sunday, 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 Christopher Peterson is to star in the festivities, sitting in a supersized red high heel shoe suspended high above the crowds at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.

The event marks Peterson’s first time in the shoe after being chosen to take over for Key West drag queen Sushi, who “hung up the heel” following her 25th year as a New Year’s Eve icon. Peterson — who even plans to sing live while perched in the shoe — is renowned for his one-man EYECONS show at the island’s La Te Da, where he impersonates women including Marilyn Monroe, Cher, Joan Rivers and Lady Gaga.

Street viewing of the entertainment and “drop” is free and open to the public. A limited number of tickets for a VIP balcony party overlooking the stage is offered each year; call New Orleans House at 305-293-9800 for VIP ticket availability.

Down the street outside Sloppy Joe's Bar, 201 Duval St., the focus of frivolity is on a gigantic manmade conch shell — the symbol of the Florida Keys — during the 30th annual "Dropping of the Conch Shell." Events are emceed by rooftop host DJ Sanaris and, as a huge clock counts down the seconds to midnight, the shell is to start descending from its supports to the flat roof of the legendary bar. The festivities also feature special musical guest appearances by Key West's own Mike Stack and D-Lew. No reservations or tickets are taken for the popular outdoor event. Visit sloppyjoes.com or livestream on Facebook @Sloppyjoesbarkeywest.

In the Key West Historic Seaport outside the Schooner Wharf Bar, 202 William St., the watering hole’s traditional “Lowering of the Pirate Wench” celebrates the island's colorful nautical heritage. Just before midnight bar owner Evalena Worthington, garbed as a winsome pirate wench, is to begin her descent from atop the mast of the tall ship America 2.0 as cannons boom. The free-admission event includes live music and festivities at the Schooner Wharf. Visit schoonerwharf.com.  

A “Gatsby New Year’s Eve” gala is planned at the original home of Pan American World Airways, featuring the midnight “landing” of a replica Pan Am aircraft carrying a costumed flight attendant. Today called First Flight Island Restaurant & Brewery, the structure now located at 301 Whitehead St. was the place where Pan Am’s first tickets were sold in 1927. Attractions include a full open bar, champagne, chef-manned food stations, live music and DJ performances. Attendees are encouraged to wear formal 1920s Gatsby-era costumes. For ticketing, visit firstflightkw.com/nye.

At the Ocean Key Resort & Spa, 0 Duval St. on Key West Harbor, plans call for a huge replica of a Key lime wedge to splash down into a larger-than-life margarita glass on the property’s Sunset Pier at midnight. The free event features live entertainment by Reggae Lou & the Kind Budz. Visit oceankey.com/key-west-sunset-pier/.

In addition, the Hard Rock Café at 313 Duval St. is to be the site of VIP party and “guitar drop” to welcome 2024. Beginning at 9 p.m., the party is to feature a live DJ, prime rib dinner and complimentary cocktail, VIP seating on the property’s outdoor patio and balcony overlooking Duval, and unrivaled viewing of the guitar’s descent at midnight. Tickets are required and attendees must be age 21 or older. Visit hardrockcafe.com/location/key-west/.

While the listing here outlines New Year’s Eve highlights in Key West, celebrations around the Florida Keys also include waterfront fireworks displays, elegant dinners and other colorful festivities. A complete roster of holiday activities and special events throughout the Keys can be viewed at fla-keys.com/calendar/.