If your clients want to escape the winter weather, the Florida Keys & Key West offer a subtropical spin on holiday traditions. From sparkling lights to unique island celebrations, the 125-mile-long island chain is the perfect destination for those seeking warmth and holiday spirit. Here are some highlights of holiday happenings in December and January.
Waterfront Winter Wonderland (through Dec. 28, 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.
Harbor Walk of Lights (through Jan. 31, Key West)
Stroll along the Key West Historic Seaport’s Harbor Walk of Lights, where the holiday magic includes a 20-foot-tall Fishing Buoy tree and a charming Lobster Trap tree. These creative displays, set against the backdrop of the harbor, are illuminated nightly through the end of the month.
Key West Artisan Market (Dec. 22 and 29, Key West)
Get into the holiday spirit with a visit to this open-air bazaar featuring unique gifts, handmade crafts and live entertainment. Located at 1801 White Street, the market showcases local artists, performers and chef-prepared delights from 10 a.m. to 2 p.m.
Holiday Sights & Festive Nights Tours (through Dec. 23, Key West)
Hop aboard Old Town Trolley or the Conch Tour Train for a festive 60-minute tour showcasing the best-decorated homes and neighborhoods in Key West. With multiple evening departures, these tours are a delightful way to experience the island’s holiday charm.
Lighting of the Historic Inns (Dec. 22, Key West)
Step into Key West’s history during the final night of the Holiday Historic Inn Tours. Discover unique architecture, lavish holiday decorations and festive treats at some of the island’s most iconic inns from 6 to 8 p.m.
Key West New Year’s Eve “Drops” (Dec. 31, 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.
For more information, visit fla-keys.com/calendar.
