New Years Traditions in Key West

New Years holidays are for saying goodbye to the old and welcoming in the new. In Key West, you'll have several great celebrations to enjoy and to do just that. When you visit you'll already be at the southernmost point in our country, so come prepared to shrug off all that weighs you down and start the New Year happier, healthier, lighter in spirit and excited for the future. Here are some of our favorite traditions and we know they'll become your favorites, too. Best of all, they each pair nicely with a premier vacation rental from our collection!

Fringe Theater Presents An Evening Lost With Lillian Baxter

1970s TV icon Lillian Baxter just had her show cancelled. What’s a "everything's coming up roses" girl to do? Industrial musicals, game shows, sitcoms, and Broadway for a start! Lillian reminds us that what is lost can always be found. The New Years Eve performance is at 7 p.m. in the Little Room Jazz Club

Old Island Restoration Foundation Presents An 1860s or 1960s Costume Gala

Travel back to the 1960s for this 60th year anniversary themed New Years Eve party. Come be a part of the fabulously dressed 21-plus crowd for this exclusive event at the Garden at the Oldest House Museum. The porch will also be open to watch the revelers promenade on Duval Street. The fun starts at 6:00 pm with dinner at 8:15pm.

New Years Eve Shoe Drop Celebration

Click your heels and come on down to watch a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.

New Years Eve Conch Shell Drop At Sloppy Joe's

Cheer the end of 2019 with the drop of a gigantic manmade conch shell to the flat roof of Sloppy Joe's Bar. Join in as thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. We'll be dancing in the street while counting down to midnight!

New Years Eve Pirate Wench Drop At Schooner Wharf

AAargh ye ready to salute Key West's rowdy seafaring roots? Meet us at Key West's Historic Seaport by midnight to watch a winsome pirate wench descend from the top of the mast of the tall ship America 2.0 to the blasts of a cannon. Scallywags can rock out to live music all day with dancing and festivities at the Schooner Wharf Bar.

Key West Dachshund Walk

You'll be walking in a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through picturesque downtown. This is really something to bark about when you watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.

Featured Property: Casa Del Rio - Monthly Rental

4 Bedrooms | 2 Baths | Sleeps 8

Now, it's time for us to show you how to make the most of your New Years traditions. Make plans to spend a month or longer at our Casa Del Rio vacation rental! This spectacular home is situated perfectly near many great shops, restaurants, and attractions. Take the short walk down White Street to Higgs Beach and the White Street Pier. Let your dreams soar to the valuted ceilings with exposed Dade County pine wood beams. The backyard continues the entertaining space, featuring a fabulous in-ground pool with a refreshing waterfall, outdoor dining space, multiple lounging areas, and a hammock to top off your tropical New Years celebrations!

Reserve from our collection of Key West vacation rentals  or call our vacation planners at 305.619.4880!