New Year’s Eve celebrations in the southernmost city traditionally feature balmy temperatures and a warm welcome for revelers fleeing colder climes. Chief among Key West’s festivities are five 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 Duval Street, enjoying a quirky island tradition dubbed the “Red Shoe Drop.” Renowned female impersonator Christopher Peterson will star in the festivities, sitting in a supersized red high heel shoe suspended high above the crowds while singing live during his descent down the facade of 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.
Street viewing of the entertainment and “drop” is free and open to the public. VIP seating is available by contacting Bourbon Street Pub.
Down the street outside Sloppy Joe’s Bar, 201 Duval St., all eyes turn to a gigantic manmade conch shell — the symbol of the Florida Keys — atop the bar for 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 starts its descent. The festivities also feature musical appearances by Key West’s own Mike Stack and D-Lew. No reservations or tickets are taken for the popular outdoor event.
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 nautical heritage. Just before midnight bar owner Evalena Worthington, garbed as a pirate wench, will 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.
A “Gatsby New Year’s Eve” gala is planned at First Flight Island Restaurant & Brewery, the original home of Pan American World Airways. New Year’s Eve features the midnight “landing” of a replica Pan Am aircraft carrying a costumed flight attendant. The building at 301 Whitehead St. is 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 tickets, 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/.
