
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.

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.
