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Key West Holiday Fest

11/24/2021 - 6:00pm to 12/31/2021 - 6:00pm

Holiday Fest in Key West

Key West Holiday Fest Through Tuesday, Dec. 31 The Harborwalk area at the Key West Historic Seaport, from Greene to Grinnell streets, will glimmer with maritime-themed holiday displays and offer unique events throughout the season. Other festival highlights include tours of historic lighted inns and a boat parade with decorated vessels and good cheer.

Wednesday, Nov. 24, through New Year’s Eve, Key West Harbor Walk of Lights at the Historic Seaport: Revel in a wonderland of light-bedecked palm trees, Christmas trees, ships, shops, restaurants and watering holes, decorated for the holiday season from Lazy Way Lane at the Green Street Plaza to the Ferry Terminal at Grinnell Street.

Monday, Nov. 29, City of Key West Tree Lighting Ceremony, 6 p.m. at Bayview Park.

Tuesday, Nov. 30, Lighting of the Menorah, 5:30 p.m. at Bayview Park.

Wednesday, Dec. 1, 8th annual POSH (Paws Often Steal Hearts) fundraising event for the Florida Keys SPCA: A catered gala-style affair at the Audubon House & Tropical Gardens with live music, silent auction, raffle prizes, food and libations.

Friday, Dec. 3, Pet Pictures with Santa, 6 to 8 p.m.: Pack up Fifi and Fido and delight in Pet Pictures with Santa at the Christmas tree at the foot of William Street at the Key West Bight Marina.

Friday, Dec. 3, 4 to 8 p.m.: Wesley House Family Services BeLighted Bike Ride and Holiday Village at Coffee Butler Amphitheater: Celebrate the holidays in good cheer with a Belighted Bike Ride through the streets of Key West, pre-ceded by a family friendly pre-party with Santa Claus, music, crafts, games, food trucks, goodies for the kids and a “Best Bike” contest. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House. Bike ride departs at 8 p.m.

Saturday, Dec. 4, Key West Hometown Holiday Parade, 7 p.m.: Delighted spectators line the streets for the homegrown parade that kicks off at Bayview Park and travels along Truman Avenue and Duval Street with festooned floats and marching groups consisting of adults, children, and elves, along with assorted hoofed and whis-kered friends.

Saturday, Dec. 11, Annual Parade of Paws & Holiday Bazaar at Higgs Dog Park, 10 a.m. to 2 p.m. (9 a.m. check-in): Benefits the Florida Keys SPCA. Costumes encouraged!

Saturday, Dec. 11, Schooner Wharf 30th Annual Key West Lighted Boat Parade, 8 p.m.: A parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights with its array of shops, restaurants and watering holes, all decorated for the holidays.

Dec. 15-17, Sugar Rum Cherry: A Burlesque Nutcracker: A naughty but nice holiday 2-act reverie at Key West Theater that features a bevy of burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic.

Saturday, Dec. 18, A Positive Step 5K Rudolph Red Nose Run: Don festive holiday jammies and join in the PJ Edition, starting and ending at the Southernmost Beach Café, 1405 Duval St. Runners and walkers of all ages and abilities are welcome.

Tuesday, Dec. 31 – New Year’s Eve: For a midnight toast, chose between an abundance of uniquely Key West New Year’s Eve celebrations, including the Conch Shell Drop at Sloppy Joe’s Bar on Duval Street and the world-famous Red High Heel Drop at the Bourbon St. Pub.

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