New Year’s Eve in Key West to Feature Dazzling ‘Drops’

Lighthearted takeoffs on the traditional ball drop in New York’s Times Square are to highlight New Year’s Eve in Key West, the southernmost city in the continental United States. And because “winter” in the subtropical spot means balmy breezes rather than blizzards, revelers can leave heavy coats and boots behind as they head out to welcome 2025.

Standout celebrations Tuesday, Dec. 31, include the midnight “drop” of female impersonator Randy Roberts in a spangled super-sized red high heel shoe. Thousands of people are expected to gather outside the Bourbon St. Pub/New Orleans House complex, located at 724 Duval St., as Roberts takes center stage at the annual extravaganza.

Roberts is best known for his live vocals and riveting show at Key West’s La Te Da Cabaret, where he depicts iconic female performers including Cher and Bette Midler. He has also appeared on “America’s Got Talent.”

Roberts is to entertain the audience while perched high above the crowd in the famed red shoe. In addition, spectators can enjoy a sizzling streetside show beginning at 9 p.m. and featuring local and national performers.

Just before midnight, the shoe carrying Roberts is to be lowered from the complex’s balcony to the accompaniment of cheers and applause from the crowds below — landing as midnight strikes and 2025 begins.

Street viewing of the show and “red shoe drop” is free. Revelers can purchase VIP tickets for exclusive balcony viewing, a top-shelf open bar and plentiful hors d’oeuvres. Tickets are to be on sale starting Dec. 1; call 305-293-9800 or 888-293-9893 (no online sales). Visit neworleanshousekw.com/about-us/.

Party people on lower Duval Street can watch the 31st annual “drop” of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval St. Festivities are emceed by a rooftop host and, as a huge clock counts down the seconds to midnight, the giant shell begins to descend. Live music inside Sloppy Joe’s rounds out the revelry. Visit sloppyjoes.com.

In the Key West Historic Seaport, New Year’s Eve merriment is centered around the Schooner Wharf Bar, 202 William St., and recalls the island’s colorful seafaring heritage. Just before midnight a “pirate wench” is to be lowered from atop the mast of the tall ship America 2.0 — completing her descent as the clock strikes and cannons boom to welcome 2025. The event includes live music, dancing 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 Pan Am’s first ticket office in 1927. Attractions at the ticketed soiree include a full open bar, chef-manned food stations, live music and DJ performances. Attendees are encouraged to wear formal 1920s Gatsby-era costumes. Visit firstflightkw.com/nye.

While New Year’s Eve highlights in Key West are listed here, other celebrations also are planned in the Florida Keys. A complete roster of holiday activities and special events in the island chain can be viewed at fla-keys.com/calendar/.

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