The High Heel Drops At Midnight on New Year's Eve – Only in Key West

Sun. December 29, 2019 10:15 AM by Ross Forman

Key West, FL - The city of Key West, Florida was, up until a few years ago, one of the few must-finally-visit stops on my travel journey. Then I finally went and have since returned a few more times, and will continue to visit the Southernmost City in the U.S.

The weather, the vibe, the food, the ocean activities, the Jimmy Buffet flavor and sound ...Key West is just a cool place to relax, definitely a must-visit on my list.

I just have to visit Key West once when it's really busy, to see what it's really like.

That starts with New Year's Eve.

Am thinking a year from now, as we prepare to welcome in 2021, I will celebrate in Key West – to watch The Shoe and the accompanying shenanigans.

Jeffrey Smead, the Director of Marketing at Island House Resort in Key West, said New Year's Eve in Key West is "pure insanity."

That sounds enjoyable.

"This tiny island becomes inundated with revelers who want to welcome the New Year with us," he said. "You have to navigate Duval Street based on where you want to end up around midnight. The crowds in front of certain spectacles get started hours before (midnight).

"Being there in person is the best way to really enjoy the humor (at midnight) in dropping a drag queen in a giant stiletto. This is where the quirky side of Key West really shines."

Key West every December 31 is known worldwide, thanks to CNN, for The Red High Heel Drop, starring local drag sensation Sushi. From the balcony of the New Orleans House, Sushi descends in a giant red high heel shoe. VIP balcony tickets usually sell out within hours and Duval Street overflows with spectators who party into the wee hours.

"The gay bars and gay resorts are gangbusters during (the) week," leading to New Year's Eve, Smead said. "There's no denying a dominant LGBT presence," throughout the city on New Year's Eve.

In fact, New Year's in Key West is so crazy that Island House sells out every year by April or May.

New Year's Eve in Key West is simply, "The perfect place to be," said Patrik Gallineaux, National LGBT Ambassador and Brand Manager for Stoli Group, USA. "(Duval Street is) buzzing with excitement; (it is) so much fun to watch people stop and point up at Sushi's high heel shoe the days leading up to New Year's in anticipation of the 'Big Drop.'

"Sushi climbs into the shoe (at about 11 p.m.) and there is always the small panic that she could fall out, but once that countdown starts with CNN cameras rolling, there is nothing more glamorous and stunning to ring in a new year than Sushi in her self-constructed couture gown descending confidently and fabulously to the Duval Street stage outside Bourbon Street Pub."

Gallineaux welcomed 2019 in Key West.

"While the LGBTQ community was well represented (at the New Year's celebration), I was thrilled how many straight men and allies wanted their turn in Sushi's shoe," for a photo-op, Gallineaux said. "Stoli is a presenting sponsor (for New Year's in Key West) with a focus on entertainment, and we are thrilled that global singing sensation Beth Anne Sacks will be joining us to headline this year."

At a past New Year's celebration in Key West, Gallineaux kissed CNN correspondent John Zarrella live on-air with Anderson Cooper and Andy Cohen watching.

Key West also, of course, is a wild party in early-June when the city celebrates Pride – and that's also when and where Stoli wraps up its annual bartender challenge. The Stoli Key West Cocktail Classic, which has always included a Chicago representative, shines the spotlight – through amazing, one-of-a-kind cocktails – on LGBT bartenders from across North America.

The winner of the Stoli competition is determined, then honored, during Key West's Pride Parade.

"Key West Pride is huge for us, especially since we are a main hub of action," Smead said. "The younger generation has really benefited from being exposed to Key West thanks to the Stoli Cocktail Classic. We love how it brings so many new faces who end up falling in love with the island and the people who live here."

What is Island House like during Pride?

Sold-out, packed, crazy, sexy and intense, Smead said.

"I love all the people who make this (Key West Pride) Week an annual destination event, and I look forward to seeing each and every one of them (in) early June," Gallineaux said. "I am very proud of the exceptional partnership between Stoli and the City of Key West as helmed by the Key West Business Guild. Watching Pride grow so exponentially is something special, and the sanest form of madness I know."

The 7th Stoli Key West Cocktail Classic wraps up in June 2020.

The Chicago finals of the event, to determine the Chicago representative in Key West, is tentatively slated for April 18 at Sidetrack – with an exciting new element, Gallineaux confirmed.

"The city of Milwaukee will be participating, bringing a bus-load of fans along with the winner of a recent Stoli LGBTQ+ local bartender competition (in that Wisconsin city), and we could see additional cities participate as well, making this truly a Chicago/Lake Michigan regional event for the first time," he said.

Another people-packed time to visit Key West is in late-October – for the annual Fantasy Fest, a 10-day celebration, with costumes, body paint and more. There also is the Captain Morgan Fantasy Fest Parade with 50-plus decorated floats along Duval Street.

Key West definitely lives up to the hype and Island House is the perfect host. The popular gay resort invested more than $250,000 into renovations of its pool, bar and pool deck in 2019.

For more information:

City of Key West:

Island House Resort: