I hope you had a wonderful Thanksgiving with family and friends. I spent the morning making a Keto green bean casserole (which was a big hit, BTW) as my contribution to the Bourbon St. Pub’s annual Turkey Turnabout fundraiser.

Rooster Santa hat Key West

Festive signs of the season are cropping up all over Key West. Even indigenous roosters (or their artisan-crafted cousins) are decked out like Santa’s helpers.

The well-attended event was a blast and benefited the Sister Season Fund, which provides financial assistance to hospitality/tourism-related industry employees temporarily out of work due to illness, accident or a natural disaster. Not only does Bourbon St. offer a mouthwatering buffet with turkey and all the fixings during the event, but the staff also dresses up in drag, making for a hilarious evening of entertainment (on and off the stage).

If you missed the Turkey Turnabout, don’t worry — Key West has many more seasonal events lined up for December. Here are just a few of my favorites that are sure to put your “holiday spirit” into overdrive.

Key West Hometown Holiday Parade. The family-friendly procession takes me back to my childhood days with its small-town charm and radiant holiday spirit. The annual parade has a little bit of everything to entertain people of all ages with its marching bands, school groups, motorized and non-motorized floats (all decorated to the hilt with gleaming holiday lights) and lively community participation. The parade kicks off at 7 p.m. Dec. 4 at Truman Avenue and White Street. Spoiler alert: attendees will most likely spot a larger-than-life Santa or two.

Old Town Trolley Holiday Lights & Sights Tours. In addition to loving parades, Key West locals absolutely adore decking their historic homes with elaborate holiday lights and decorations. Neighborhoods are transformed into little winter wonderlands (minus the cold and snow, of course). Hour-long trolley tours offer a fantastic opportunity to check out the island’s dazzling holiday displays. Tours are offered on many evenings in December aboard the Old Town Trolley and also the Conch Tour Train.

An “elf” offers holiday goodies at Island City House, one of the enchanting locations that will be visited and explored by revelers during the 2021 Holiday Historic Inn Tours scheduled Dec. 10 and 17. (Photo by Carol Tedesco, Key West Holiday Fest)

Holiday Historic Inn Tours. This two-night event is scheduled Dec. 10 and 17 from 6 to 8 p.m. Each evening showcases a different selection of some of Key West’s grandest historic inns, with unique architecture bursting with holiday ambiance. You can also nibble on delicious treats and sip libations as you explore the fascinating structures. Complimentary transportation to each property is provided via trolley, or you can use your own favored mode of transportation. Tickets can be purchased by calling 305-296-4959 or on Keystix.com any day before the date of the tour.

Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade. OMG, the Lighted Boat Parade makes for such a fun evening. The extravaganza is celebrating its 30th anniversary this year, setting sail at 8 p.m. Dec. 11 from the Key West Bight and harbor. The dark ocean waters become illuminated as decorated dinghies, fishing craft and classic tall ships light up the Key West Historic Seaport and harbor areas. You can view the dozens of creatively bedazzled vessels from the Schooner Wharf, the parade’s headquarters, and from various bars, restaurants and resorts on and around the seaport’s harborwalk and docks.

I recommend arriving early (around 6-ish), so you can enjoy the harbor walk’s fantastic holiday decorations — and a special performance by the Bahama Village Music Program featuring steel band rhythms and Caribbean calypso Christmas carols along the waterfront. It’s truly a magical “only in the Keys” celebration.

Are you planning a holiday trip to the Keys? Well, it has never been easier to visit us with increased airlift to Key West International Airport, including more nonstop service from major U.S.  airports than ever before.  So I hope to see you soon enjoying some of our unique “island-style holiday cheer” in the Florida Keys & Key West.

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