Holiday Cheer and Community Care Light Up Key West Through New Year's Eve
KEY WEST, Fla. (December 19, 2025) — The 20th annual Key West Holiday Fest has transformed the southernmost island into a sparkling tropical wonderland this December, drawing thousands to celebrations where lighted bike parades, boat parades, and a lobster trap Christmas tree showcase the island's unique holiday spirit.
The festivities, which kicked off Thanksgiving Eve when thousands gathered to light the Historic Seaport's Harbor Walk of Lights, have rolled through the month with distinctly Keys flair. Festively outfitted revelers aboard illuminated bicycles dazzled onlookers with a rolling light show during the Wesley House BeLighted Bike Ride. Nearly 30 watercraft, festooned with illuminated white balloons, shimmering snowflakes, and a Key West chicken lighting the way, dazzled spectators during the 34th annual Schooner Wharf Bar Lighted Boat Parade.
This weekend brings the Running of the Elves 5K and Jingle Bell Mile on Saturday, December 20, starting at 6 p.m. from Dante's Key West Pool Bar. The festive race benefits Reef Relief and includes free entry to the Waterfront Winter Wonderland Festival for all participants.
As the celebrations have unfolded, the holiday spirit has extended beyond lights and laughter to address real community needs. On December 11, Mayor Danise "Dee Dee" Henriquez and the City Commission unanimously approved a $75,000 emergency food-relief program to support local organizations serving families facing food insecurity during the holiday season. The city awarded its first grant to AH Monroe, with five additional applications currently under review. Qualified nonprofits can apply for grants of up to $7,500 through December 31 at cityofkeywest-fl.gov.
"I am honored to help support our community and those in need this holiday season," said Mayor Henriquez. "We issued our first check to AH Monroe, and I'm proud of how quickly we can get these funds to the organizations serving our neighbors in need."
The island celebration doesn't end after Christmas. On New Year's Eve, Key West welcomes 2026 with four uniquely tropical "drops" that put a distinctly island spin on Times Square tradition. Revelers can witness the Red Shoe Drop featuring a drag queen in a spangled high-heel shoe at Bourbon St. Pub, the 31st annual Conch Shell Drop at Sloppy Joe's Bar, the Lowering of the Pirate Wench from the tall ship America 2.0 at Schooner Wharf Bar complete with cannon fire, and the "landing" of a flight attendant in a replica Pan Am aircraft at First Flight Island Restaurant & Brewery's Gatsby-themed gala.
From North Carolina mountain pines at the MARC House Christmas tree lot to holiday-themed 5Ks and uniquely Key West New Year's Eve countdowns, Key West Holiday Fest captures the island's ability to blend tropical paradise with heartfelt tradition.
Key West Holiday Fest, an annual island-wide celebration orchestrated by numerous entities, is presented in part by the Lodging Association of the Florida Keys and Key West and the Monroe County Tourist Development Council. For a complete calendar of events through New Year's Eve, visit KeyWestHolidayFest.com.
High-resolution images, photo credits, and captions are available at this link.
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A flock of illuminated reindeers lead Santa, elves, and canine companions in a rolling sleigh during the Wesley House Family Services BeLighted Bike Ride, one of the festive events transforming Key West into a tropical holiday wonderland throughout December. Celebrating its 20th year, Key West Holiday Fest is an annual island-wide celebration presented in part by the Lodging Association of the Florida Keys and Key West and the Monroe County Tourist Development Council. To learn more, visit www.KeyWestHolidayFest.com. (Carol Tedesco/Florida Keys News Bureau)
Well-known Key West pugs Delilah (left) and Sampson pose with Santa Claus during the All Animal Clinic "Pet Pictures with Santa" event at the Key West Historic Seaport, one of many family-friendly celebrations during Key West Holiday Fest. Donations from the photo event benefit the Boys and Girls Club of Key West. Key West Holiday Fest, celebrating its 20th year, is presented in part by the Lodging Association of the Florida Keys and Key West and the Monroe County Tourist Development Council. For more information, visit www.KeyWestHolidayFest.com. (Carol Tedesco/Florida Keys News Bureau)
Thousands surround a towering lobster trap Christmas tree during the Thanksgiving Eve ceremonial lighting of the Key West Historic Seaport, marking the start of the 20th annual Key West Holiday Fest. The Harbor Walk of Lights stretches from Lazy Way Lane to the Ferry Terminal at Grinnell Street, creating a sparkling seaside wonderland with Christmas trees, thousands of twinkling lights, and maritime-themed displays. Key West Holiday Fest continues through New Year's Eve and is presented in part by the Lodging Association of the Florida Keys and Key West and the Monroe County Tourist Development Council. For more information, visit www.KeyWestHolidayFest.com. (Carol Tedesco/Florida Keys News Bureau)
Cheeky elves (left to right) Hallie Keaveney of Big Pine Key, Sacha Glynn of Key West, and Erin Mahoney of Stock Island spread holiday magic at the towering lobster trap Christmas tree during the Thanksgiving Eve ceremonial lighting of the Key West Historic Seaport. The lighting marked the start of the 20th annual Key West Holiday Fest, an island-wide celebration presented in part by the Lodging Association of the Florida Keys and Key West and the Monroe County Tourist Development Council. For more information, visit www.KeyWestHolidayFest.com. (Carol Tedesco/ Florida Keys News Bureau)
Santa Claus waves from atop a brightly lighted U.S. Coast Guard Station Key West vessel led by Rudolph the Red-Nosed Reindeer during the 34th annual Schooner Wharf Bar Lighted Boat Parade at the Key West Historic Seaport. Nearly 30 illuminated watercrafts participated in the parade, one of many celebrations during the 20th annual Key West Holiday Fest presented in part by the Lodging Association of the Florida Keys and Key West and the Monroe County Tourist Development Council. For more information, visit www.KeyWestHolidayFest.com. (Carol Tedesco/ Florida Keys News Bureau)
Key West Mayor Danise "Dee Dee" Henriquez (second from right) presents the city's first emergency food relief grant to AH Monroe's Leah Stockton (center) as part of the City Commission's $75,000 program to support local organizations serving families facing food insecurity during the holiday season. Also pictured, from left: Assistant City Manager Michael Turner, Mayor for the Day Bill Marraccini, and Assistant City Manager Rod Delostrinos. The city is currently reviewing five additional grant applications, with funding available through December 31 at cityofkeywest-fl.gov. (Photo provided by City of Key West)
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