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Thurs, Dec 1, 6-9:30pm, The 9th Annual POSH (Paws Often Steal Hearts) Florida Keys SPCA Fundraiser at the Audubon House & Tropical Gardens; a catered gala event featuring live dance music by SUENALO!, raffles, and a silent auction.

Fri, Dec 2, 4:00-8:00pm, Wesley House Family Services Holiday Village and BeLighted Bike Ride at Coffee Butler Amphitheater: Celebrate the holidays with a family friendly party with Santa Claus, music, crafts, games, food trucks, goodies for the kids, and a “Best BeLighted Bike” contest. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House Family Services. Belighted Bike Ride through the streets of Key West departs at 8:00pm.

Sat, Dec 3, 11am-2pm, Pet Pictures with The Grinch: Bring your critters to Hank’s Hair of the Dog Saloon, 409 Caroline Street, for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a 501(c)(3) non-profit senior dog sanctuary.

Sat, Dec 3, 7:00pm, Key West Hometown Holiday Parade: Spectators line the streets for the homegrown parade which kicks off at Bayview Park and travels along Truman Ave and Duval Streets with festooned floats and marching groups consisting of adults, children, and elves, along with assorted hoofed and whiskered friends.

Sunday, Dec. 4, 4:00-6:00pm, the Woman’s Club Open House at 319 Duval St. includes Santa Claus, Snacks, and Music by the Bahama Village Children’s Choir and the Key West Orchestra.

Sun, Dec 4, 6:00-8:00pm, Pet Pictures with Santa: 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. Proceeds benefit the Boys & Girls Club of the Keys.

Dec 7-11, Nutcracker Key West: Some 60 local children and adults and 15 professional dancers from around the world join together in 2022 to produce this outstanding historical recreation of Key West’s enchanting version of the Nutcracker ballet at the Tennessee Williams Theater.

Dec 8, 11-13, 16-23, Conch Tour Train Holiday Sights and Festive Nights Tours: Multiple nightly tours depart from Key West High School and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

Dec 8-23, Old Town Trolley Holiday Lights & Sights Tours: Multiple nightly tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.

Fri, Dec 9, Holiday Historic Inn Tours – Night 1, 6:00pm-8:00pm: Visit and tour four beautifully decorated island locales: Key West Butterfly Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation Inn, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings.

Fri, Dec 9, 5:00-9:00pm, 5th Annual Holiday Concert & Bazaar at Custom House Museum: This festive free party features some of Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show.

Sat, Dec 10, 10:00am-2:00pm (9:00am check-in), 9th Annual Parade of Paws & Holiday Bazaar at Higgs Beach / Higgs Dog Park: Benefits the Florida Keys SPCA. Costumes encouraged!

Sat, Dec 10, 8:00pm, Schooner Wharf Annual Key West Lighted Boat Parade: A glittering 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.

Sat, Dec 10 and Fri, Dec 16, Visit Santa at the North Pole, 12:00-2:00pm: Kids of all ages can visit with Santa at the Southernmost “North Pole,” conveniently located in the upstairs level of the historic Shops at Mallory Square, 291 Front Street. Letter writing stations and a mailbox will be available for the younger set.

Sunday, Dec 11, 1:00-3:00pm, meet the Monroe County Sheriff’s Office Animal Farm inhabitants during “Christmas on the Farm Open House” located at the Stock Island Detention Center, 5501 College Rd. Free; donations appreciated!

Fri, Dec 16, Holiday Historic Inn Tours – Night 2, 6:00-8:00pm: Visit and tour four beautifully decorated island locales: Hemingway’s Library @ Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel, and Island City House, and explore their unique architecture and history while enjoying sweet and savory holiday treats and libation samplings.

Sat, Dec 17, 7:00am check-in, 8:00am start time, 14th A Positive Step 5K Rudolph Red Nose Run: Don your festive holiday jammies and join in the 14th A Positive Step 5K Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café, 1405 Duval Street. Runners and walkers of all ages and abilities are welcome to participate; first 100 registrants receive a free t-shirt.

Sun, Dec 18, 10:00am-2:00pm, Key West Artisan Market, the Holiday Shop Local edition: The curated offerings of more than 75 local artists will be available at Sonny McCoy Indigenous Park along with food, libations, and music performed by local musicians.

Sun, Dec 18, 11:00am-3:00pm, Holiday Classic Car Show: See classic cars from a variety of eras at the official show of the Florida Keys Southernmost Car Club, and choose a People’s Choice winner with your votes. Located at the Conch Republic Seafood Company parking lot at the corner of Greene and Elizabeth Streets. Attendees are asked to bring an unwrapped toy for the Monroe County Domestic Abuse Shelter. 

Sun, Dec 18, 5:00pm, City of Key West Menorah Lighting Ceremony at Bayview Park.

Dec 25, Holiday Jazz in the Gardens, 5:00-7:00pm: The Gardens Hotel at 526 Angela street welcomes holiday-goers to festive outdoor jazz in its famous garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly.

“Key West Holiday Fest is a sparkling, month-long celebration of the season, celebrated in our unique tropical island style,” commented Jodi Weinhofer, President of the Lodging Association of the Florida Keys and Key West. “From lighted parades on land and sea, to enchanting inn tours, musical performances, stage events, and New Year’s Eve extravaganzas, there’s something wonderful for all ages happening here.”

Key West Holiday Fest is presented by Berkshire Hathaway Keys Real Estate, Opal Key Resort and Marina, Ocean Key Resort, The Lodging Association of the Florida Keys and Key West, and the Monroe County Tourist Development Council. For links and information, visit

WKWJ does not necessarily endorse all the events posted.

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