Holiday Weekends Florida-Style

Three easy getaways to jump-start the season.

Fort Lauderdale
213 miles, 3 hr. 30 min. drive from Orlando

Plying the waters of Fort Lauderdale’s New River and Intracoastal Waterway is an army of vessels lit up like festive firecrackers against dark, inky waters. When the 42nd Seminole Hard Rock Winterfest Boat Parade takes over this South Florida city on Dec.14, you’ll want to be sitting in the grandstand cheering on the sailboats, power boats, barges, yachts and even paddleboards—all decked out with strings of twinkling lights and decorated around themes from flamingos and pirates to Santa and snowmen. With 100 contestants competing, it’s no wonder boat captains add special effects to get the judges’ attention. Expect blaring renditions of Jingle Bells and dancing snowflakes projected on canvas sails. The spectacle, one of the biggest boat parades in the U.S., begins at the Broward Center for the Performing Arts on Riverwalk and travels 12 miles north to Lake Santa Barbara in Pompano Beach. A pre-show elf brigade ushers in the non-motorized kayakers and paddleboarders, followed by the pyrotechnic barge that kicks off the parade with plenty of flash and boom.

Best viewing is off fashionable Las Olas Boulevard alongside the New River (the Riverside Hotel hosts ticketed viewing parties on its patio and dock) or at Hugh Taylor Birch State Park, where an advance ticket purchase will score you a reserved and assigned spot in the grandstand. Park gates open in the afternoon so you can get your photo taken with Santa, rock out with live entertainment and munch on festival food. winterfestparade.com

Key West
395 miles, 7 hr. drive from Orlando

At this southernmost town, often called the end of the line for Florida travelers, the holidays turn tropical in true Key West style. You can be sure there’s plenty of holiday spirit—or should we say spirits—to share, starting with a merry bar crawl down Duval Street, the main thoroughfare in the city’s historic Old Town district. Besides joining revelers dressed in elf, reindeer and Santa suits in the local bars, you can hop on the Holiday Lights Conch Tour Train (Dec. 13, 15-16, 18-19, 21-22) for an hourlong ride, weaving through maze-like streets and passing elaborately decorated homes wrapped in crimson ribbons and evergreen garlands with penguin and snowman figurines standing guard. Join in the singing of Christmas carols as the trolley rolls along in the balmy night air.

Then there’s the Holiday Historic Inn Tour (Dec. 6 and 13) a two-hour, self-guided walking tour through Key West neighborhoods. Innkeepers invite you inside their bed-and-breakfasts to swoon over the festive trimmings and indulge in a glass of wine and holiday treats. A favorite stop is The Mermaid & The Alligator B&B, a 1904 Victorian charmer where outside a life-size stuffed Santa in a Hawaiian shirt relaxes in a hammock between two palm trees and inside the Christmas tree is dripping with mermaid- and alligator-themed ornaments.

At the Historic Seaport, the Harbor Walk of Lights (Nov. 27-Dec. 31), a boardwalk lined with Christmas trees and towering palms wrapped in strands of flickering bulbs, draws crowds with ongoing holiday entertainment. The star event here is the Schooner Wharf Bar & Galley Lighted Boat Parade (Dec. 14). Find prime viewing at the Schooner Wharf Bar, where the boats cruise close to the dock and judging station. Order conch fritters and a frozen Rum Runner as you hoot and holler for your favorite boat.

The fun continues to New Year’s Eve when a 6-foot-tall, red high-heel shoe, cradling the flamboyant drag queen Sushi, drops from the balcony of the Bourbon Street Pub/New Orleans House. Crowds will fill Duval Street to celebrate 2014 when Sushi pops a champagne bottle at the New Year’s Eve Shoe Drop Celebration (Dec. 31). fla-keys.com

Captiva Island
237 miles, 4 hr. drive from Orlando

Visit the Gulf side of the state for a small-town Christmas on cozy Captiva Island. Tucked at the end of Sanibel Island in Southwest Florida, the island hosts the Captiva Holiday Village (Nov. 29-Dec. 15). Most of the action takes place in the tiny downtown area around Andy Rosse Lane, which stretches from the Gulf of Mexico to Pine Island Sound and is dotted with outdoor cafés and funky art galleries.

On Dec. 7, residents who zip around Captiva year-round on their golf carts now compete with their neighbors to outshine one another in the Decorated Golf Cart Parade—an event filmed last year for the Travel Channel’s proposed Xtreme Xmas show. Don’t think there’s much you can do with a golf cart? You’ll be surprised when the Polar Express, a cart converted to look like a black choo-choo train, rolls down the street, or metallic silver star-shaped balloons and white confetti create a winter wonderland on wheels.

Come on the weekend of Dec. 14 and you’ll be treated to a host of holiday festivities such as the Lighted Boat Parade. For this small, intimate boat parade, only 100 lights are required, but once again the locals get in the holiday spirit so expect thousands of colorful bulbs, giant Santas and fireworks.

Watch from The Green Flash restaurant or book a spot on Captiva Cruises’ Lady Chadwick to view it from the water and then sail in the parade as one of the last boats. The flotilla of about 20 watercraft travels along Roosevelt Channel as merrymakers toast the boats gliding through pitch blackness. Afterward, head to Andy Rosse Lane to celebrate with the winners. captivaholidayvillage.com 

Where to Stay

B Ocean, Fort Lauderdale
Nestled between the Intracoastal Waterway and the Atlantic Ocean, this waterfront property is across the street from the beach and the Hugh Taylor Birch State Park, where prime grandstand parade seating is available. bhotelsandresorts.com

Casa Marina, Key West
Close enough to walk to Old Town, yet set off from Key West’s craziness, this elegant historic waterfront hotel was a project of railroad tycoon Henry Flagler, built by his architects in 1918 after he died. waldorf.hilton.com/casa_marina

’Tween Waters Inn Island Resort, Captiva Island
Named so because it sits between the Gulf of Mexico and Pine Island Sound at the narrowest part of the island, the resort is perfect for lolling on the beach or scouring the shore for seashells. Later, the resort’s shuttle will whisk you into town for the festivities. tween-waters.com