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



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.


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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 (spiked), 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.

Recommended for Holiday Attractions because: 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.

Claudia's expert tip: Bring a lightweight jacket. Even though Key West temps are on the warm side, you might get chilled out on the water at night.

Read more about Classic Harbor Line Key West →


Sebago Watersports
Photo courtesy of Schooner Appledore II


How would you like to actually be on one of the vessels in the Key West Lighted Boat Parade? You can participate in the action aboard 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, but you'll also 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. Tickets are $59 for adults $29.50 for children ages 4-11.

Recommended for Holiday Attractions because: For a truly unique vacation experience, hop aboard the Sebago Schooner Appledore II and be a part of the holiday parade.

Claudia's expert tip: Wear your Santa hats and Christmas sweaters; it gets cool out there on the water at night.

Read more about Sebago Watersports →




Cruising Old Town Key West by bicycle is one of the best ways to enjoy the whimsical holiday decorations. Traditional architectural details are transformed, as gingerbread millwork is laced with twinkling lights and icicles. Giant stars and wreaths dangle from wraparound balconies, while red ribbons and green garland stripe the columns. No doubt, the owners are spurred on by the yearly competition, mixing in candy canes, reindeer and snowmen with the bougainvillea, frangipani and hibiscus across their lawns. Eaton Bikes carries mountain bikes, road bikes, beach cruisers, tricycles and more. Rentals include free bike delivery and pick up anywhere in Key West.

Recommended for Holiday Attractions because: Take a leisurely bike ride through the neighborhoods to enjoy the colorful and creative holiday decorations.

Claudia's expert tip: If it's been a while since you've ridden a bike, give it a test-drive before you hit the streets.

Read more about Eaton Bikes →


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The Conch Train Holiday Lights Tour is one of the easiest ways to take in the elaborate trimmings draped across the historic homes and inns. The tour makes many a top 10 list 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. Visit their website for dates and times.

Recommended for Holiday Attractions because: The Conch Train Holiday Lights Tour is a festive way to take in all the elaborate trimmings draped across the historic homes and inns.

Claudia's expert tip: The tour includes special Holiday Lights glasses.

Read more about Conch Tour Train →




The Little White House house is a living museum that has been impeccably restored and is a sight to behold during the holidays. It's decorated exactly as it was in World War II right down to the Christmas tree lights and their collection of 1940s and 1950s ornaments. In December, they offer exclusive VIP tours complete with champagne, hot chocolate, treats and more. Presidential Christmas Cards are showcased throughout. As a bonus, you can pick up presents in the gift shop. Their White House Collector ornaments make a great stocking-stuffer. Key West has served as a presidential retreat since 1880 when Ulysses S. Grant visited the island. Harry Truman reportedly despised living in Washington and viewed this as his sanctuary. He spent 175 days of his presidency here from 1946 through 1952.

Recommended for Holiday Attractions because: The Little White House is decorated for the holidays using their collection of 1940s and 1950s ornaments and Presidential Christmas cards.

Claudia's expert tip: Looking for the perfect gift for a history buff? Pick up one their White House Collector ornaments, custom designed to honor this state heritage landmark.

Read more about Harry S. Truman Little White House →




Book tickets early for Key West's tropical version of the Nutcracker ballet at Tennessee Williams Fine Arts Center. Presented every other year, the tale of young Clara's dreamlike visit to the land of the Sugarplum Fairy is transformed into an island and undersea fantasy. The production stars a 15-member professional corps de ballet along with more than 50 Keys children and other local performers. Named after the Key's other famous writer-in-residence, the theater hosts a variety of December programming like musical tributes to classic Hollywood television specials. The Arts Center is also home to the South Florida Symphony, and the event calendar includes a range of live performances from Broadway theater such as Mamma Mia to concerts with famous musicians like Kristin Chenoweth.

Recommended for Holiday Attractions because: December programming includes musical tributes to classic TV holiday specials and a truly Key West approach to the Nutcracker ballet.

Claudia's expert tip: The Nutcracker is only presented every other year, so tickets are in high demand. Buy early if you want to see this colorful spectacle.

Read more about Tennessee Williams Fine Arts Center →




Despite being far away from the North Pole, Key West Inns in December are decorated as if they are expecting Santa as a guest. Revel in that holiday spirit--and Key West's unique architecture and heritage--during the Holiday Historic Inn Tours. Presented by the Key West Innkeepers Association, the tours feature five festive island properties each evening. The tour is self-guided, and guests can start at any property. Trolleys provide transportation between stops. The innkeepers are on hand to share insights into the location and its history, and they welcome you inside for libations and light appetizers. Tickets may be purchased by calling the Key West Lodging office or on the website keystix.com and can be picked up the night of the tour at the first property after 5:00 pm.

Recommended for Holiday Attractions because: The historic inns in Key West are decorated for the holidays as if they are expecting Santa himself.

Claudia's expert tip: Start at The Mermaid & The Alligator, where Santa rests in a hammock on their front lawn.

Read more about Holiday Historic Inn Tours →


The holiday season in Key West kicks off each November with the "Bight" before Christmas festivities along the Historic Seaport. The Nautical Harbor Walk of Lights features the Fishing Buoy Christmas Tree, a real pine Nautical Christmas Tree and the Lobster Trap Christmas Tree all honoring the Maritime History of Key West. They go live with much fanfare at Greene and Elizabeth Street, and the festivities stretch the entire length along the seawall past Greene Street, William Street and Margaret Street to the K.W. Ferry Terminal. Take an evening stroll after dining at one of the waterfront restaurants, and do some holiday shopping at the cute shops along the path. Throughout December, the Bight plays host to a variety of events like holiday musical performances, pet photos with Santa, a violin charity jam, a classic car show and the Lighted Boat Parade.

Recommended for Holiday Attractions because: The Nautical Harbor Walk of Lights creates a festive atmosphere along the water, guaranteed to get you into that holiday spirit.

Claudia's expert tip: Best viewing for the Christmas tree lighting is on the Harbor Walk at Greene and Elizabeth Street.

Read more about Key West Bight Before Christmas →




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 (305-293-9800), a disco party goes non-stop with drag queens entertaining on an outdoor stage. At midnight, Sushi, the diva of drag, 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 (305-296-2388). At the final countdown, a giant manmade conch shell descends from the roof. For something a little more mellow, the Ocean Key Resort (305-296-7701) drops a Key lime wedge into a giant Margarita as the clock strikes twelve. Not to be outdone, Schooner Wharf Bar (305-292-3302) lowers a pirate wench from the top of a tall ship's mast. Cannons punctuate the end of the year.

Recommended for Holiday Attractions because: Who wants to shiver in Times Square when you can wear flip-flops and watch everything from drag queens to pirate wenches drop at midnight?

Claudia's expert tip: Book a spot at one of the many viewing parties above street-level, you'll be much more comfortable--and have access to a bathroom.

Read more about New Year's Eve Celebration →




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 riggings 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 the Schooner Wharf, where the boats turn around for the judging station.

Recommended for Holiday Attractions because: During this annual parade, boats dress to impress with elaborate decorations woven into the masts and rigging.

Claudia's expert tip: If you'd rather be a participant in the parade instead of a just a spectator, most of charter boats sell tickets.

Read more about Key West Lighted Boat Parade →


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Meet 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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