
Lighthearted takeoffs on the traditional ball drop in New York’s Times Square highlight New Year’s Eve in Key West. And because “winter” in the subtropical spot means balmy breezes rather than blizzards, revelers can leave their winter coats behind.
Standout celebrations on Tuesday, Dec. 31, include the midnight “drop” of female impersonator Randy Roberts in a spangled super-sized red high heel shoe. Thousands of people gather outside the Bourbon St. Pub/New Orleans House complex, 724 Duval St., as Roberts takes center stage at the annual extravaganza.
In addition, a streetside show on the ground below begins at 9 p.m. and features local and national performers.
Just before midnight, the shoe carrying Roberts is lowered from the complex’s balcony, landing as midnight strikes and 2025 begins.
Street viewing of the show and “red shoe drop” is free. VIP tickets are available for exclusive balcony viewing, and include a top-shelf open bar and plentiful hors d’oeuvres. For tickets, call 305-293-9800 or 888-293-9893 (no online sales).

Party people on lower Duval Street can watch the 31st annual “drop” of a gigantic manmade conch shell 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 to midnight, the giant shell begins to descend.
At the Key West Historic Seaport, Schooner Wharf Bar is the center of New Year’s Eve merriment. Just before midnight a “pirate wench” is lowered from atop the towering 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.
A “Gatsby New Year’s Eve” gala is planned at the original home of Pan A.m. 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 building 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.