Are you trying to plan a last minute escape and are wondering Where to Stay in the Florida Keys The Winter Season?
New Year’s Eve partiers unwilling to endure cold-weather festivities, such as the traditional “ball drop” in New York’s Times Square, can find exuberant celebrations and far warmer temperatures in the Florida Keys. Key West revelers can choose from several lighthearted takeoffs on the Times Square gala as midnight approaches Saturday, Dec. 31.
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Where to Stay in the Florida Keys for the Winter Season
At the Bourbon St. Pub complex, 724 Duval St., renowned drag queen Sushi is to star in the “Red Shoe Drop” festivities for the 25th year. Seconds before midnight, a super-sized red high heel carrying the elaborately gowned Sushi will be lowered from the complex’s balcony toward the cheering crowd below. Past “Red Shoe Drops” have been featured on CNN.
As well as Sushi’s lively banter prior to the “drop,” spectators can enjoy scheduled performances by notable female impersonators and other local and national talents on a street-side stage.
Street viewing of the entertainment and “drop” is free and open to the public. A limited number of tickets for a VIP balcony party overlooking the stage is offered each year; call New Orleans House Guest House at 305-293-9800 for VIP ticket availability.
Party people on lower Duval Street can watch the “drop” of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe's Bar, 201 Duval St. Festivities are to be hosted from the rooftop by DJ Sanaris and, as a huge clock counts down the seconds to midnight, the supersized shell begins to descend.
Live music and dancing inside Sloppy Joe’s round out the revelry. No reservations or tickets are taken for the popular outdoor event. Visit sloppyjoes.com.
In the Key West Historic Seaport, New Year’s Eve merriment is centered around the Schooner Wharf Bar, 202 William St., and celebrates the island’s colorful seafaring heritage.
Just before midnight, a “pirate wench” is to be lowered from the top of a majestic tall ship’s mast — completing her descent as the clock strikes and cannons boom to welcome 2023. The event includes live music, dancing and festivities at the Schooner Wharf. Visit schoonerwharf.com/.
Revelers also can applaud a huge replica of a Key lime wedge splashing down into a larger-than-life margarita glass on the Sunset Pier at Ocean Key Resort & Spa, 0 Duval St., paired with a performance by The Beatle Band; the “landing” of a flight attendant in a section of a replica aircraft during a ticketed Gatsby-style party at First Flight Island Restaurant & Brewery, 301 Whitehead St., whose historic building is known as the birthplace of Pan Am; and the offbeat “tuna drop” at the Smokin’ Tuna Saloon, 4 Charles St. Visit facebook.com/SunsetPierKeyWest/, firstflightkw.com and smokintunasaloon.com.
While the listing here outlines New Year’s Eve highlights in Key West, celebrations elsewhere in the Florida Keys include waterfront fireworks displays, gala dinners and other colorful festivities. A complete roster of holiday activities and special events throughout the Keys can be viewed at fla-keys.com/calendar/.
Quite a few family-friendly hotels across the Keys are offering incredible holiday deals and programs! From bountiful holiday dinners, ice skating next to the white-sand beaches, meet and greets with Santa’s reindeer, and 12 days of mojitos, there is certainly something for everyone!
Where to Stay in the Florida Keys The Winter Season
For The Luxurious Traveler - Isla Bella Beach Resort & Spa in Marathon, FL
Right off the famous seven-mile bridge, this luxury resort lay where the Gulf of Mexico meets the Atlantic. Amidst a clear, cerulean sea and white sandy beach.
Watch a famous Keys’ sunset over the glimmering waters from your balcony, or during dinner at the beachfront restaurant, Mahina.
Christmas and New Year’s offerings include a synthetic ice skating rink, Santa’s reindeer meet and greet, Christmas day buffet, New Year's Eve DJ celebration, and more (Christmas menu here).
For The Adventurous Traveler - Ocean’s Edge Resort & Marina in Key West, FL
This luxurious resort is the perfect opportunity to treat yourself. Spend the afternoon fishing, parasailing, or scuba diving if you want a holiday trip with momentum, or slow down by lounging at one of the six swimming pools for some R&R.
Christmas and New Year’s offerings include photos with the Key West Island Santa, the night before Christmas full moon paddleboard excursion, poolside Christmas movie screenings, A Cuban Christmas Dinner, and a New Year's Day “Hangover” party, including a grilled cheese station, bloody mary bar, and live DJ!
For The Partier - Havana Cabana Resort in Key West, FL
For a stay with nonstop fun to celebrate the end of a long year, Havana Cabana is THE party hotel in the Florida Keys — tropical music, and a warm, vibrant lobby greet you as you step into the next closest thing to Havana itself.
This Christmas, happy hours begin at 10am. Live music throughout, the buzzy pool area features the largest pool in Key West, leafy cabanas, a variety of games, a Mojitos Pool Bar, and authentic Cuban fare at the hotel's Floridita Food Truck.
Enjoy the resort’s 12 Days of Mojitos for each of the 12 days leading up to Christmas, featuring both a fruity and frozen mojito variety named after Santa’s 12 reindeer.
Find out more about what there is to do - and where to stay - in the Florida Keys!
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