Holiday Fun in the Florida Keys!

USA Today’s TEN Best HOLIDAY Attractions in The Florida Keys


Yuletide Spirit with a Twist: Key West’s 10 Best Holiday Attractions

Claudia Miller


While it may seem counter-intuitive to head to a tropical locale to catch the holiday spirit, Key West in December is a wonderland of festive surprises. The warm temps might very well be the reason residents approach the yuletide season with such unbridled enthusiasm. Visitors can enjoy a bevy of merry events and attractions throughout the month.

The historic Old Town architecture takes on a new glow, as the gingerbread millwork is laced with twinkling lights and icicles. Giant snowflakes hang from wraparound balconies, and red ribbons and green garland stripe the columns. Candy canes, penguins and snowmen mix with the bougainvillea, frangipani and hibiscus along the lawns. The Holiday Lights Conch Train Tour, Holiday Historic Inn Tour–or even just cruising around on a bike–are  great ways to see the decorations.

The Historic Seaport plays host to a series of events as part of their Bight Before Christmas celebration. This includes the Nautical Harbor Walk of Lights and the Key West Lighted Boat Parade. Festivities culminate in an island-wide New Year’s Eve Celebration where various bars drop things way more interesting than a crystal ball. Think pirate wench, giant conch shell, and even a drag queen inside a red super-sized, high-heel shoe. For a full calendar of events, visit the Key West Holiday Fest website.




You won’t find better seats for two of Key West’s best holiday celebrations–the Lighted Boat Parade and New Year’s Eve at Schooner Wharf–than aboard the America 2.0. This sleek schooner is a near replica of the first boat to win the America’s Cup in 1851 with teak decks and mahogany trimmings. The holiday cruise is a three hour sailing adventure under the glowing moonlight and stunning decorations. As the other vessels pass by, you’ll enjoy hot cider, conch chowder and cookies along with complimentary beer, wine, champagne, soda and water. Tickets are $85 for adults and $45 for children. At their adults-only New Year’s Eve bash, experience all the action front and center with VIP dockside access to the Schooner Wharf Bar. The famous midnight “Lowering of the Pirate Wench” happens right above you from the rig. Tickets are $165.


Sebago Watersports

Photo courtesy of Schooner Appledore II
How would you actually like to be on one of the vessels in the Key West Lighted Parade? You can participate in the action aboard the Sebago’s Schooner Appledore II, a traditional sailing vessel built by the Harvey Gamage Shipyard in South Bristol, Maine. Not only will you get to see the elaborately decorated boats up close, you’ll enjoy a holiday party on the water. Enjoy a glass of bubbly, boutique wine, sangria, beer or other festive libations paired with fresh fruit and artisan cheeses. You won’t find a more unique vacation experience in December. Wear your Santa hats and Christmas sweaters; it gets cool out there on the water at night. Get ready to smile for the cameras, as you float past the judges station at Schooner Wharf Bar.



The Little White House The Conch Train Holiday Lights Tour is one of the easiest ways to take in all the elaborate trimmings draped across the historic homes and inns. The Conch Tour Train makes a lot of top 10 lists for good reason. Their bright yellow trains have been winding the shady streets of Old Town since 1958. Normally the tour is a pretty straightforward rundown of the local sights and rich island history, but in December, the train pulls double duty for the Holiday Lights Tour. Coasting through the balmy night, the hour-long ride usually leads to caroling–perhaps encouraged by the cider and cookies served prior to the ride. The train is also available for private charters.





Ring in the New Year in the Florida Keys where you can enjoy balmy temps and a variety of celebrations where they’ll be “dropping” things way more interesting than a crystal ball. In front of the Bourbon Street Pub, a disco party goes non-stop with female impersonators entertaining on an outdoor stage. At midnight, Sushi, a drag queen diva dressed in a glittering ball gown, descends from the top balcony inside a red 8-foot-long high heel. Down the block, you can join the revelry spilling out onto Duval Street from Sloppy Joe’s Bar. At the final countdown, a giant man-made conch shell descends from the roof. Not to be outdone, Schooner Wharf Bar lowers a pirate wench from the top of a tall ship’s mast. Cannons punctuate the end of the year


As holiday parades roll down Main Street in small towns across America, Key West residents string garlands and lights on everything from dinghies to mega-yachts and take their festivities to the water. At Key West’s annual Lighted Boat Parade in the Historic Seaport, you’ll be dazzled by their creativity. Leaping dolphins, dancing candy canes, peace doves, toy soldiers and of course, Santa’s sleigh glitter across the water as they coast past. The charter boats dress to impress with elaborate decorations woven into the masts and rigging like a 20-foot spinning Christmas ornament or a 30-foot Art Deco angel. While great views can be found at any of the bars, restaurants and resorts around the Historic Seaport and harbor areas, the best perch is at Schooner Wharf, where the boats turn around for the judging station

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Claudia Miller


Claudia Miller has been writing about South Florida for over 17 years–seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad…  More About Claudia




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