Florida Keys Holidays to Shine with Lights and Subtropical Warmth

FLORIDA KEYS — Bright and beautifully “belighted” subtropical holidays in the Florida Keys & Key West are filled with warmth, inspiring good cheer throughout the 125-mile-long island chain. From Key Largo to Key West, the 2024 holiday season features spirited events such as lighted boat parades, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.

Select Keys holiday events are outlined below, while additional Florida Keys & Key West events can be found at fla-keys.com/calendar.

Nightly Through Jan. 31: Harbor Walk of Lights. Key West. The Harbor Walk of Lights at the Key West Historic Seaport stretches along the harbor past Greene, William and Margaret streets to the Key West Ferry Terminal. Highlights  include la 20-foot-tall Fishing Buoy tree, a Key West Lobster Trap tree and lighted displays featuring fish, manatees, flamingos and more along with brilliantly-lit palm trees. The displays will be illuminated nightly through Dec. 31. Visit keywestchristmas.org. 

Dec. 9-23: Old Town Trolley's Holiday Sights & Festive Nights Tours. Key West. The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m. Visit trolleytours.com/key-west/christmas-holiday-tours or call 855-623-8289 or 305-296-6688.

Dec. 13-23: Conch Tour Train's Holiday Sights & Festive Nights Tours. Key West. Lively Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 8 and 8:30 p.m. Included are holiday lights glasses as keepsake items. The hourlong tour, with holiday caroling, takes riders past the island's most elaborately decorated houses, buildings and neighborhoods. Visit conchtourtrain.com/key-west-christmas-holiday-tours/ or call 305-707-5775 or 305-296-6688.

Dec. 13-28: Waterfront Winter Wonderland. Key West. The Waterfront Winter Wonderland transforms the Coffee Butler Amphitheater at Truman Waterfront Park into a festive holiday experience for all ages. The family-friendly event features an ice-skating rink, rides like a Ferris wheel and carousel swings, games, live music, light displays and more. The amphitheater’s vendor village offers food and local artisan goods perfect for holiday shopping. Enjoy visits with Santa, a kids’ craft tent and festive celebrations. Admission is $12, with children 5 and under free. Additional costs apply for ice skating and rides. The fun takes place at 21 Quay Rd. Visit waterfrontwinterwonderland.com.

Dec. 21: Kiki's Sandbar Lighted Boat Parade. Little Torch Key. Festively decorated boats are set to cruise the waters around Little Torch Key, creating holiday spectacles both on the water and in the skies with a dazzling drone show. For information call 305-780-7753. The Kiki's boat parade is the last one for this season, with many having taken place the second weekend in December. 

Dec. 22 and 29: Artisan Market. Key West. A Key West holiday shopping tradition filled with one-of-a-kind gifts, the open-air bazaar is set for selected Sundays from 10 a.m. to 2 p.m. at 1801 White St. Markets feature Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit facebook.com/KeyWestArtisanMarket or call 305-509-3385.

Dec. 31: Key West New Year's Eve “Drops.” Key West. Ring in 2025 with a “conch shell drop” at Sloppy Joe's Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying a female impersonator at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.; and the lowering of a pirate wench at midnight from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St. Revelers can also witness the “flight” of a uniformed “stewardess” in a section of a replica aircraft and enjoy a ticketed Gatsby-style party at First Flight Island Restaurant & Brewery, 301 Whitehead St. Visit sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest/ and firstflightkw.com.

Florida Keys events calendar: fla-keys.com/calendar/