Celebrate New Year’s Eve in Key West

Planning a new year's eve vacation? Whether you're looking for a romantic couples weekend or a family-friendly vacation spot, Key West is the perfect NYE trip!

When it comes to ushering in the new year, is there anything more fun than celebrating while on vacation? And if you’re vacationing in Key West, Florida, the area’s New Year’s festivities will just add to the excitement of your trip. Whether you’re traveling with your family, a group of friends or that special someone, there are plenty of entertaining ways to ring in 2018 in the Conch Republic. Once you arrive in Key West, you can park your rental car and easily navigate the island’s main attractions by foot, pedicab, trolley or by renting a bike.

Traveling as a Family

Head to Key West, the southernmost city in the continental U.S., for New Year’s, and you’ll find kid-friendly events that the entire family will enjoy.

Nearly 200 short-legged, long-bodied pups and their owners take over the streets during the annual Key West Dachshund Walk at noon on New Year’s Eve to celebrate the official dog of Key West. Because of their little legs, the parade route is somewhat miniature so the dachshunds don’t tire too quickly from the day’s festivities. The route encompasses the 400 block of Fleming Street, the 500 block of Duval Street and the one-block-long Appelrouth Lane in the heart of Old Town. If you happen to have your four-legged family member with you, he or she can be a part of the fun as an “honorary dachshund” for the day. Old Town is easily walkable and bikeable from many popular hotels. Street parking is available nearby, and paid parking can be found at the nearby post office on Whitehead Street.

Old Town in Key West Travelers and locals can bike through Old Town in Key West year-round.

Keep the fun going with a Glass Bottom Boat and Reef Eco Tour with Fury Key West. This two-hour tour offers families the chance to peer into North America’s only living coral reef to see elkhorn, brain coral and more. Sit on the sun deck or in the enclosed, air-conditioned viewing area as your captain and crew point out the most interesting marine life along the way.

Traveling as a Couple

With its waterfront views, fantastic dining scene and, of course, stunning sunsets, Key West is a lovely place for couples to ring in the new year.

Start the day in Old Town with a visit back in time at the Ernest Hemingway Home & Museum, where the legendary author lived in the 1930s. In the writing studio that adjoins the house, Hemingway penned such classics as For Whom the Bell Tolls, Death in the Afternoon and Green Hills of Africa. Stroll through the gardens and soak in the warm Florida sun. You may even spot one of the six-toed cats that still live on the property, descendants of Hemingway’s own six-toed cat. And be sure to check out the swimming pool. When it was built in 1938, it was the first in-ground pool in Key West and the only swimming pool within 100 miles.

Watch the year’s final sunset from any number of spots on the island, including Mallory Square, located on the water on the northwest side of the island, a short walk from Old Town. Mallory Square hosts world-famous sunset parties every night that include magicians, musicians, art, food and more. Then, settle in for one last dinner of the year. Make reservations in advance at any of the fine dining spots in Key West such as Square One, Michaels or Antonia’s. Or, stop in for a bite to eat at a more casual restaurant like The Cafe (vegetarian), Red Fish Blue Fish or Pepe’s Cafe, the oldest restaurant in Key West.

Mallory Square Watch the sun go down over the ocean at Mallory Square.

When it’s time to welcome the arrival of the new year, make your way to the Ocean Key Resort & Spa  and watch as an oversized Key lime wedge splashes into a huge margarita glass on Sunset Pier just as midnight strikes.

Traveling with Friends

If you and your crew are reveling in Key West this New Year’s Eve, the parties start early and carry on well into the next morning in this tropical oasis.

Sloppy Joe’s, the famous spot on Duval Street frequented by Hemingway during his days in the Keys, starts the festivities bright and early at 9 a.m., and the party goes well past midnight. Beginning at 10 p.m., festivities hosted by a rooftop emcee include dancing in the street, live music and a gigantic, man-made conch shell (the symbol of the Florida Keys and the Conch Republic) that falls amid confetti and streamers at midnight to usher in the new year. Partying outside is free, but if you want to go into the bar itself, a cover charge ranging from $3-$10 may apply.

Key West’s Sloppy Joe’s Head to Key West’s Sloppy Joe’s to usher in the new year with music and dancing. Photo by Roger W, Flickr.

Farther down Duval Street, Sushi the drag queen, a local icon, descends at midnight from a supersized red high-heel shoe at the Bourbon Street Pub, just as she has for two decades. VIP balcony tickets are available for a bird’s-eye view of the festivities above and below, including performances by female impersonators and other entertainment.

Alternatively, when night falls and midnight approaches, head for the Schooner Wharf Bar for the “Lowering of the Pirate Wench,” where co-owner of the Schooner Wharf Bar, Evalena Worthington, dresses up like a pirate wench and is lowered from the mast of a tall ship during an illuminated countdown to midnight. Or spend the afternoon listening to live music and enjoying the waterfront setting leading up to the night’s festivities, guaranteeing your spot to watch the lowering. The event is free, and complimentary hats, party favors and horns are passed out so everyone can welcome 2018 pirate-style with a cannon fire.

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About the Author

Susan B. Barnes, aka travlin’ girl, is a travel writer who enjoys exploring the world as much as her own Florida backyard and sharing discoveries with her readers. Follow her travels online on Facebook, Twitter and Instagram.