See a drag queen drop from a giant red shoe — everything goes on New Year’s Eve in Key West

This offbeat little tropical island never disappoints when it comes to any holiday.

But buckle up for New Year’s Eve if you’re headed to Key West to usher in 2020. Here’s a guide to several wacky “drops” and other events along the island chain, including the Middle Keys, Key Largo and Islamorada.

The New Year Drops

Sushi, the drag queen drop

Bourbon Street Pub, 724 Duval St.

Streetside concert starts at 9 p.m.

New York has the Times Square Ball while Key West has a human being being lowered to the ground from above Duval Street.

Yes, Sushi the drag queen is Key West’s traditional drop. Gowned and coiffed, Gary Marion as Sushi will descend inside a supersized red high heel from outside the Bourbon Street Pub, as throngs of revelers ring in the new year below.

A free stage show starts at 9 p.m. on Duval Street while balcony tickets run $150 each and include a buffet, an open bar and private restrooms.

Conch shell drop

Sloppy Joe’s Bar, 201 Duval St.

Down the street outside Sloppy Joe’s Bar, the focus of a very early 2020 will be a man-made conch shell — the symbol of the Florida Keys — during the annual “Dropping of the Conch Shell.”

A rooftop host aside a huge clock counts down the seconds to midnight and the shell begins to descend from its supports to the flat roof of the legendary bar. No reservations or tickets are needed. Visit sloppyjoes.com.

‘Pirate Wench’ drop

Schooner Wharf Bar, 202 William St.

At the Key West Historic Seaport outside the Schooner Wharf Bar, the watering hole’s traditional “Lowering of the Pirate Wench” celebrates the island’s seafaring heritage. Just before midnight, a pirate wench will start to descend from atop the mast of the tall ship America 2.0 as cannons blast. The event includes live music and festivities at the Schooner Wharf.

Other drop spectacles take place near or just off Duval Street:

• An oversized Key lime wedge splashes down into a giant margarita glass at the Sunset Pier at Ocean Key Resort and Spa, 0 Duval St.

• A flight attendant lands in a section of a replica aircraft at First Flight Restaurant and Brewery, 301 Whitehead St. The historic building is billed as the birthplace of Pan American World Airways. They’ll also have a Great Gatsby 2020 New Year’s Eve Party that starts at 8 p.m.

• At the Smokin’ Tuna Saloon, 4 Charles St., a tuna, of course, drops for the new year.

The 15th Annual Key West Dachshund Walk

12 p.m., Tuesday, Dec. 31, Fleming and Whitehead Streets

As many as 200 dachshunds are expected for this short parade at noon on New Year’s Eve. Participants gather at 12 p.m. at Fleming and Whitehead streets. Then, with their owners, they’ll all march along a three-block parade route that includes Duval Street.

This is a sprint, not a marathon. Chihuahuas have been known to crash in a flash mob. Other breeds also show up. Registration is not required. Costumes are encouraged along with donations of dog and cat food for the Community Pet Pantry.

Events outside Key West

Isla Bella Beach Resort

1 Knights Key Boulevard MM 47, Marathon, FL

In the Middle Keys, this resort plans to celebrate its first New Year’s Eve with dinner and dancing. Events include a gourmet buffet, live music and a champagne toast at midnight.

Cheeca Lodge and Spa

Mile marker 82, oceanside

The sport fishing capital Islamorada will help welcome the new year with midnight fireworks at the beach of this luxurious resort and spa. The party includes live music and dancing on the beach. Visit cheeca.com/experience/holidays-at-cheeca/ or call 305-664-4651.

Morada Bay Beach Cafe

Mile marker 81.6, bayside

6 p.m. for the first seating of dinner. 7 p.m. for the beach party.

Also in Islamorada, party people can ring in the New Year with a party and fireworks at midnight on the beach at Morada Bay Beach Cafe. The evening also includes a large beach party with live music, a beach barbecue, cocktails and performers. For prices, click here or call 305-664-3225.

Sundowners

Mile marker 104, bayside

9 p.m.

And at the top of the keys in Key Largo, a fireworks display will light the sky above Blackwater Sound. Set to start at 9 p.m., the event is hosted by Sundowners and includes live music. To reserve seats for a special New Year’s Eve dinner, click here.

This story was originally published December 27, 2019 at 1:30 PM.

Gwen Filosa

Miami Herald

Gwen Filosa covers Key West and the Lower Florida Keys for FLKeysNews.com and the Miami Herald and lives in Key West. She was part of the staff at the New Orleans Times-Picayune that in 2005 won two Pulitzer Prizes for coverage of Hurricane Katrina. She graduated from Indiana University.