Key West New Year's Eve: The Midnight Drops, Sunset Sails and Where to Stand

Each drop has its own venue, its own start time and its own crowd. The table below compares what drops, where it drops and when the party started last year, from the bars' listings and Visit Florida Keys. Street entry is free at every site.

The Red Shoe at Bourbon St. Pub

A giant red high-heel shoe is lowered from the second-story balcony at 724 Duval Street, hanging about 15 feet above the street, while a costumed drag star rides inside. Thousands pack Duval in front of the pub and the drop is broadcast live. In past years the street show with local and national performers started at 9 p.m., and the latest listing puts the start about 10 p.m., so arrive early either way.

Sushi, the performer who rode the shoe for 25 drops, retired after her last ride in 2022. The bar now picks the star through a national contest called If the Shoe Fits, and last year the contest chose Mulan Alexander. The performer for this New Year's Eve is not announced yet.

VIP balcony tickets, which include a balcony view, a top-shelf open bar and hors d'oeuvres, are sold by phone only at 305-293-9800 or 888-293-9893. The price is not published, so call. Free street viewing needs no ticket on Duval Street.

The Conch Shell at Sloppy Joe's

This New Year's Eve is the 33rd annual conch shell drop at Sloppy Joe's, 201 Duval Street at the corner of Greene. A lit giant manmade conch shell descends onto the flat roof at midnight while a rooftop emcee works a big countdown clock. Local artist Tobias McGregor proposed the idea in 1993 as a way to get the whole crowd counting down together, and it has run nearly every New Year since.

Festivities last year started around 10 p.m. with a rooftop DJ and street dancing, and a live feed of the roof plays indoors on the bar's Sloppy-Tron. No reservations or tickets are needed. Duval is shoulder to shoulder by about 11 p.m., so claim a spot early if the conch is your pick.

The Pirate Wench at Schooner Wharf

At the quieter end of the night, in the Historic Seaport, Schooner Wharf Bar lowers a pirate wench from the mast of the tall ship America 2.0. The wench is owner Evalena Worthington, and the descent finishes exactly at midnight, followed by cannon fire. Last year live music ran from 11:30 a.m. with dancing and party favors through the evening, and there is no ticket.

It sits away from the Duval crush. The same ship sells the America 2.0 schooner sunset sail from the dock right in front of Schooner Wharf Bar, so you can sail the last sunset of the year on her and watch the wench come down her mast at midnight. See more on the Historic Seaport before you go.

Key Lime Wedge, Chicken and the First Flight Plane

At Sunset Pier, Ocean Key Resort, 0 Duval Street, a giant Key lime wedge drops into an oversized margarita glass at midnight. Admission is free, and in past years free live music started at 5 p.m., so check the resort's Sunset Pier page closer to the date for the act and confirmation. New last year, Bobby's Balls Bar at 828 Duval Street added a chicken drop: a huge chicken figure lowered on a boom, honoring Key West's free-roaming roosters.

First Flight Island Restaurant & Brewery at 301 Whitehead Street, the building that was Pan Am's first ticket office, runs a ticketed Great Gatsby party with an open bar, chef-manned food stations, live music and a DJ. At midnight a replica Pan Am aircraft lands with a costumed flight attendant. Buy tickets in advance, 1920s dress encouraged.

The price is not published.

Sunset Celebration at Mallory Square

The final Sunset Celebration of the year runs at Mallory Square, 400 Wall Street, starting about two hours before sunset, so be there around 3:50 p.m. Magicians, jugglers and artists work the crowds as the sun goes down over the water, and the party on the square rolls straight into the evening. No admission fee is listed on the official page.

It is the easiest way to start the night without a booking, and you are already in Old Town when the drops begin. Read our full guide to Mallory Square for what the square is like the rest of the year.

Sunset Sails That Get You Back for the Drops

Each of these sails runs about two hours, so you are back on the dock long before the street parties start. The cheapest open bar on the water is the Sebago open-bar sunset sail at $69.95, with an open liquor bar, champagne and live music. The Fury live-band sunset sail at $73 puts a full band on a 65-foot catamaran, and Fury has run its New Year's Eve sunset bash on this catamaran.

The America 2.0 schooner sunset sail at $127.12 is the pick if you want the Schooner Wharf connection, since you check in dockside at 202 William Street and step off at the bar that drops the wench. For a smaller boat, the adults-only champagne sail at $108.91 caps at 14 guests and is non-refundable, and the classic schooner sail with open bar at $109 caps at 22. If you want dinner on board, the sunset dinner cruise at $93 includes a buffet and open bar.

The holiday week is the most expensive of the Key West year, so book early and compare the wider range of sunset cruise options.

The six sails side by side: listed price per adult, what the ticket includes and how many people share the deck, from each operator's listing.

The times below come from last year's listings by the venues and Visit Florida Keys, plus the confirmed sunset time for December 31. Use them as a planning shape rather than a fixed schedule, because each bar publishes its own program closer to the date. The one fixed point is sunset at 5:50 p.m.

How to Use the Evening

A realistic plan looks like this. Sail the last sunset, or stand at the Sunset Celebration from about 3:50 p.m., then eat an early dinner. Fill the gap before midnight with the craft cocktail crawl, which runs five cocktails at bars mostly off Duval, or the original Duval pub crawl, five bars with a drink at each.

Then pick one drop and be standing there well before 11:55 p.m. The drops fire at the same moment, so you will see one. Duval is shoulder to shoulder by about 11 p.m., and Keys Weekly advises choosing your site early.

Families with kids in tow can book the Ghosts and Gravestones trolley, an evening ride through Old Town's haunted history.

Beachside and Blue Flamingo on December 30

If fireworks matter to you, plan around December 30. Last year Beachside Resort at 3841 N. Roosevelt Blvd. ran a free family fireworks and glow party, with a DJ from 6 p.m. and the fireworks at 9 p.m. Across the road, the Blue Flamingo hosted a 6-9 p.m. party with live music by Mike Stack & Friends and a view of the Beachside show, with free general admission.

Fireworks fans visiting around New Year's should also know that other Keys towns do fire on the night itself, with displays in Islamorada, Key Largo and Marathon on December 31. Check our events calendar for what is listed as the date gets closer.

Casa Marina on the Beach

Casa Marina Key West, the big resort on the Atlantic side, runs a full program away from the Duval crowds. Midnight at the Beach is a five-course oceanfront prix fixe at Dorada, followed by a live band and a DJ countdown. Toes in the Sand puts you at a private beach table with a tasting menu.

Both book on OpenTable. The Bebidas lawn countdown starts at 6 p.m. with food and drink for sale, opens a dance floor and cigar rolling at 8 p.m., runs a live band to 10 p.m. and a DJ to 1 a.m., with free parking. No prices are published for any of it.

If you want a dressed-up countdown without squeezing onto Duval, this is the structured option.

Restaurants Near the Drops

Several restaurants near Mallory Square have run New Year's Eve menus: RoofTop Cafe on Front Street with a holiday menu, Michael's with a prix fixe dinner, and Louie's Backyard. El Meson de Pepe sits about a block from the Sunset Celebration and is known for its Cuban cigar drop. Call each restaurant for its New Year's Eve menu and price.

Book weeks ahead, because December 31 falls in the most expensive week of the Key West year and tables near Duval go first. Our guide to where to eat in Key West covers the rest of the year's dining.

Where to Park and What Closes

Several blocks of Duval Street close to vehicles for most of the night, so driving near the drops after dark is a bad plan. The Old Town Parking Garage at 301 Grinnell Street, at the corner of Caroline, has 300 spaces, first come first served, at $6 an hour or $48 a day plus tax. The Mallory Square lot at 412 Wall Street runs $7 an hour with a $48 daily max and 100 spaces.

The city lists no special event rates, so expect those prices to hold and spaces to vanish early. The better move is to skip the car entirely and stay within walking distance of Duval and the seaport. Compare options in our guide to where to stay in Key West, and read the details on parking in Key West before you drive.

After Midnight

Duval stays packed after the drops. Walk a block or two off Duval to Simonton or Whitehead Street before ordering a ride. The city has run a New Year's Eve Safe Ride shuttle in past years, and in the year its schedule was published the last pickups were at 1:45 a.m.

No schedule has been published for this New Year's Eve, so check Key West Transit closer to the date. The free Duval Loop bus is another option earlier in the evening, though sources disagree on its hours. For crowd sense, read the page on safety and scams, and see getting around Key West for the full picture.

What the Weather Does

December averages a high of 78°F (25°C) and a low of 68°F (20°C) at the Key West airport, with the sea at about 75-77°F (24-25°C). December runs about 6 rain days, so a shower is possible but not the norm. In practice that means shorts at midnight for most people, plus a light layer if you are on the water after sunset, when the breeze off the Gulf gets cool.

If you are deciding between dates for a winter trip, our guide to the best time to visit Key West compares the whole year.

Holiday Lights and the Dachshund Walk

Old Town houses keep their Christmas lights up through the holiday week, and an evening walk through the side streets costs nothing. The annual Key West Dachshund Walk is free, needs no registration, and is family-friendly. It has historically run at noon on December 31 at Whitehead and Fleming streets, rain or shine, though one recent listing puts it on the morning of January 1, so check before you plan around it.

Link it with Key West with kids ideas for the rest of the week.

New Year's Day

The Sunset Celebration at Mallory Square runs again on January 1, a gentle way to close the trip. Hotels are at their most expensive this week, so book them months ahead. For ideas beyond the countdown, browse our things to do in Key West and the wider range of Key West tours.