Key West ‘drops’ in on 2020

Start the year at the end of the road

Key West ‘drops’ in on 2020 - A person standing in front of a crowd - Florida Keys
Gary Marion, attired as drag queen Sushi, hangs in an oversized replica of a women's red high heel over Duval Street late on Dec. 31, 2018, at the Bourbon St. Pub in Key West. ANDY NEWMAN/Florida Keys News Bureau

Key West doesn’t drop the ball when it comes to New Year’s Eve, but we drop plenty of other things, from pirate wenches, planes and drag queens to conch shells and Key limes.

First Flight Island Restaurant and Brewery will welcome a replica Pan American plane at the stroke of midnight to celebrate its location in the airline’s original and historic ticket building in Key West.

Pan Am’s official beginning dates back to October 1927, when its inaugural flight carried sacks of mail from Key West to Havana, Cuba. 

The building that housed Pan Am’s ticket office originally was at the Key West waterfront, but was later moved to Whitehead Street and today is part of the First Flight complex.

The restaurant and brewery will pair the plane’s landing with a Great Gatsby-themed party to ring in 2020.

Meanwhile, in other parts of town, Key West’s typical, though not at all traditional, New Year’s Eve festivities will include several other parodies of the ball-drop in New York City’s Times Square. 

Key West ‘drops’ in on 2020 - A group of people in front of a large crowd watching - Sloppy Joe's Bar
Crowds jam Duval Street outside Sloppy Joe’s Bar to watch a giant replica of a conch shell descend to start 2019. The Conch Shell Drop is one of six Key West takeoffs on New York City’s Times Square ball drop to mark the beginning of the new year. CAROL TEDESCO/Florida Keys News Bureau

Island events include the lowering of a conch shell from the roof of Sloppy Joe’s bar during the countdown in front of a packed Duval Street; Sushi the female impersonator will ride a giant, red, high-heeled pump from the second floor of Bourbon Street Pub/New Orleans House guesthouse; Evalena Worthington, pirate wench and owner of Schooner Wharf Bar, will descend from the mast of a historic schooner docked in front of the waterfront watering hole; and on Upper Duval Street, a towering champagne bottle atop La Te Da will tip over at midnight and “drench” the enthusiastic crowd below with confetti and streamers; and a replica Key lime will drop into a supersized margarita glass at the Ocean Key Resort on lower Duval.

There’s never any shortage of New Year’s Eve revelry in a town that takes its parties seriously and promises its guests plenty of good times — and more holiday spirits than may be advisable come New Year’s Day.

Key West ‘drops’ in on 2020 - A group of people on a stage - Schooner Wharf Bar
Evalena Worthington practices her planned New Year’s Eve descent from the top of a tall sailing vessel’s mast, dockside at the Schooner Wharf Bar late Saturday, Dec. 29, 2018, in Key West. FLORIDA KEYS NEWS BUREAU/Contributed
Mandy Miles
Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.