This Florida City Is The Best Spot In The South For Celebrating New Year's

Pack your walking shoes, and set the clocks to island time.

sushi in shoe key west

Courtesy of New Orleans Guest House

It’s time to pull out the sequins, Champagne, and witty toasts as we near the close of another year. Times Square will be lit up as the traditional ball drops, but In the South, colorful choices like a beach ball, a peach, or a fleur de lis signal it’s time to say goodbye to the old and welcome in the new.

But Key West is the spot to celebrate New Year’s Eve with drops featuring a drag queen, conch shell, or pirate wench at various points around the city. 

Known for its quirky style and boisterous bar scenes, ringing in the year in Key West is memorable. Bookending it with a few days' stay is divine. Each night, the fiery sunset is celebrated at Mallory Square with a street carnival featuring performers, psychics, musicians, and entertainers. There are butterflies, shipwrecks, and mangroves to explore. And lots of delicious food to eat your way through. Pack your walking shoes, and set the clocks to island time for some celebrating in the Conch Republic.

Sloppy Joe's Bar Conch Drop

Courtesy of Sloppy Joe's Bar

New Year’s Eve

For the most time-honored tradition, head to Sloppy Joe’s on lower Duval Street where they drop an enormous manmade conch shell. Revelers watch the descent of the symbol of the Florida Keys while a huge clock ticks down the seconds to midnight. There’s live music starting at noon, a boisterous emcee leading the crowd, and lots of cheer at this free public event.

Key West is known for pirate adventures, and the drop at Schooner Wharf Bar embodies that swashbuckling spirit. Located in Historic Seaport, the merriment starts early with three local and national acts, party favors, and Champagne. As midnight looms, party-goers hoist their drinks to toast the pirate wench lowered from the towering mast of the America 2.0, and a cannon booms to signal the new year. The festivities keep rocking until 4 a.m. with no cover charge. 

pirate wench drop

Courtesy of Schooner Wharf Bar

The Red Shoe Drop at New Orleans Guest House has been going strong for over 24 years and features renowned local drag queen, Sushi. Performances by other drag queens and top local and national talent prep the crowd for Sushi and her lively banter as she is lowered in her gigantic red high heel seconds before midnight. The drop and entertainment are free and open to the public, but for a more intimate experience, a limited number of VIP balcony tickets are available for purchase through the hotel.

Where To Stay

Southernmost Beach Resort fits the bill if you’re looking for a spot close to everything that still feels worlds away. The six-acre, award-winning Duval Street beachfront property underwent a massive renovation in 2022 adding space and coastal charm to the secluded retreat.

The exterior refresh blends the inside with the outside incorporating a palette of ocean and sky blues complemented by sand-inspired creams. Just two short blocks from the iconic concrete buoy at the Southernmost Point and a few blocks to the hustle and bustle of downtown, guests can take in the breeze from one of the oceanfront hammocks, relax on the beach, or stroll down garden paths. 

Pool and palm trees

Courtesy of Southernmost Beach Resort

Sunset Key Cottages provide a true escape amidst the revelry. The secluded, 27-acre island is only accessible by boat and located just seven minutes from the mainland.

Key West-style cottages offer luxury accommodations with wraparound verandas, panoramic views, and a beachfront spa. And pups are welcome.

interior of Sunset Key Cottages

Courtesy of Sunset Key Cottages

For a boutique hotel with an award-winning onsite restaurant right in the heart of the action, the Marquesa Hotel makes a perfect spot to lay your head down and have a fabulous meal.

Where to Eat

The roosters and cats roam free at Blue Heaven as diners munch on Caribbean and Keys specialties in a lush al fresco space. It’s also home to the most "heavenly" breakfast in Key West with dishes like Shrimp Benedict and Betty’s Banana Bread. The historic property has been the site of a bordello, a venue for Friday-night boxing matches refereed by Ernest Hemingway, a billiard hall, and more.

Blue Heaven, Key West

Courtesy of Blue Heaven

Family-owned and operated since 1984, El Siboney embraces traditional Cuban home cooking with dishes including roast pork, black beans and rice, and tostones. Or hit Café Sole, an off-the-beaten-path culinary gem serving local diver-caught hog snapper with roasted red pepper zabaglione.


Courtesy of El Siboney Key West

For a unique dining experience, take a complimentary ferry to Sunset Key for a meal at Latitudes. Sink your toes in the sand while snacking on mojo-cracked conch, yuzu glazed snapper, and seared grouper topped with jicama green apple slaw as another sun sets over the ocean. Breakfast and lunch at this picturesque spot offer al fresco dining with specialties like Key Lime Ricotta Pancakes and Key West Fish Tacos filled with tempura-fried grouper.

Latitudes on Sunset Key

Courtesy of Latitudes on Sunset Key

First Flight Island Restaurant & Brewery brews beer and then serves clams steamed in one of their ales at this historic location where Pan Am’s first tickets were sold in 1927. 

In the mornings, grab a traditional café con leche and a guava and cheese pastry at Ana’s Café Cubano, or swing by Sarabeth’s for some Key Lime Pie Stuffed French Toast to start the day.

What to Do

Escape to a world of flowering plants, colorful birds, cascading waterfalls, and over 50 species of butterflies from around the world at The Key West Butterfly & Nature Conservatory. In the learning center, guests explore butterfly anatomy, lifecycle, feeding, and the monarch’s migratory world. Check out the resident flamingos, or spend some time feeding butterflies while they flutter all around and even land on your arms.

Walk off some of New Year’s Eve’s festivities with the Key West Literary Seminar’s guided 90-minute tour of the town’s literary legacy. Tour the former homes and haunts of Tennessee Williams, Shel Silverstein, Thomas McGuane, Elizabeth Bishop, and Robert Frost while hearing stories of their lives and works. 

In a location with so many great dining options, sometimes it helps to sample some of the iconic options before committing. Key West Food Tours offers a guided 3-hour Southernmost Food & Cultural Walking Tour that takes visitors to six locally-owned establishments in historic old town. Tastings from specialty shops unique to Key West like conch fritters and key lime pie are punctuated by stories of hidden architectural gems, tropical flora, and exciting local attractions provided by local guides. 

mixed drinks in plastic cups

Courtesy of Southernmost Food & Cultural Walking Tour

Get some scuba diving in with Captain’s Corner where you can explore the legendary Vandenberg shipwreck, a World War II military troop transport vessel, or spend the afternoon poking around a reef in the National Marine Sanctuary

Danger Charters brings many of the great things about Key West together in their Sunset Sail, Snorkel & Kayak adventure. Enjoy sailing to the Key West National Wildlife Refuge, kayak mangroves, snorkel through sponge gardens, then settle in for a front-row seat to the best show in the area, sunset. It’s the perfect capstone to a week of celebrating the New Year in the Conch Republic.

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