Sunny, breezy subtropical holidays in the Florida Keys & Key West are filled with warmth and good cheer throughout the 125-mile-long island chain. From Key Largo to Key West, the 2022 holiday season features spirited events such as lighted boat parades, historic inn tours, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.
In the weeks leading up to the holidays, check out the enchanting events listed here.
The holidays are celebrated with great enthusiasm in the Keys — even by the feline population!
Now through Dec. 10: Zonta’s Festival of Trees. The Zonta Club of Marathon, a women’s service organization, offers a free-admission display of decorated trees at its 12th Annual Festival of Trees at Marathon Garden Club, 5270 Overseas Highway. Attractions also include “Lunch with the Grinch” Saturday, Dec. 10. The upscale ticketed “Toast to the Season” is scheduled that evening at the garden club with champagne, music, libations and tasty treats. A drawing for all trees and holiday baskets is set for 9 p.m. While admission to the Festival of Trees is free, raffle tickets can be purchased for a chance to win a favorite tree.
Now through Dec. 23: Old Town Trolley’s Holiday Sights & Festive Nights Tours. 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 the island city’s Mallory Square at 6:30, 7, 8 and 8:30 p.m.
Dec. 9: Key West Art & Historical Society Holiday Bazaar. The Key West Art & Historical Society hosts its sixth annual concert and holiday shopping event on the sweeping porch and walkway of the historic Custom House Museum at 281 Front St. The 5-9 p.m. free-admission event features a holiday light show produced by Key West High School’s Conch 5 Studios, unique gifts crafted by local artisans, musicians, choirs, food, libations and photos with Santa.
Dec. 9, 10 and 11: Lighted Boat Parades. Lighted and festively decorated boats, from fishing craft and cruisers to tall ships, are to cruise waters surrounding the Florida Keys. Celebrate the season with the Holiday Lighted Boat Parade of Stock Island (Dec. 9); the Key Largo Boat Parade on Blackwater Sound, themed “A Cartoon Christmas”; the Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade (Dec. 10) around the Key West Historic Seaport and harbor; or the Key Colony Beach Christmas Boat Parade (Dec. 11).
Boat parades throughout the Florida Keys combine holiday spirit and the Keys’ colorful seafaring heritage.
Dec. 9 and 16: Holiday Historic Inn Tours. Old Town Key West is filled with unique historic inns, and two Friday evenings of 6-8 p.m. tours offer a chance to glimpse lavish decorations and experience holiday cheer, treats at bed-and-breakfast properties and two popular Key West attractions.
Dec. 10: Pops in the Park Concert “Joy to the World.” Islamorada’s family-friendly, free-admission holiday concert, themed “Joy to the World,” offers traditional and pops music by the Florida Keys Community Concert Band. The Burton Bell Ringers are to be special guests. Attendees can bring chairs and blankets to the 4-5 p.m. outdoor concert at Founders Park’s amphitheater, mile marker 87 bayside.
Dec. 11: Christmas on the Sheriff’s Animal Farm. Children and adults love visiting the unique Monroe County Sheriff’s Office Animal Farm, just northeast of Key West at 5501 College Road on Stock Island. The farm, open 1-3 p.m. on the second and fourth Sundays of each month, is educational for visitors and a haven for feathered, furry and fluffy creatures that are nurtured and cared for by jail inmates. Holiday highlights include photos with Santa.
Dec. 15: Third Thursday Art Walk. Showcasing the area’s fine arts, music and culinary nuances, Islamorada’s Morada Way Arts & Cultural District features national and local artisans whose work is showcased in galleries at Morada Way between mile markers 81 and 82, as well as beer tastings and live music. Admission is free to this outdoor pre-holiday celebration. The 6-9 p.m. Art Walk is held the third Thursday of each month.
Dec. 17: Winter Wonderland at Crane Point. At Crane Point Hammock Museum & Nature Trails, 5550 Overseas Highway in Marathon, families can enjoy an evening winter wonderland. Attractions are to include reindeer ponies and Santa Claus, holiday decorations, a chocolate fountain, other seasonal treats and libations for purchase — plus a forecast of snow!
While this listing outlines a handful of the Florida Keys’ seasonal highlights, there are plenty of other colorful festivities to enjoy as well. A complete roster of holiday activities and special events throughout the Keys can be viewed here.
