Two evenings of Holiday Historic Inn Tours are set to take place during Key West Holiday Fest, offering revelers an opportunity to explore multiple enchanting locations decked out in holiday splendor. (Photo Carol Tedesco/

Key West Holiday Fest 2022 offers dazzling array of festive events
Key West Holiday Fest, the southernmost city’s annual joyous celebration of the season, is set to kick off on Wednesday, Nov. 23, 2022. Whether you delight in the fun and funky, the enchantingly elegant, or all the above, revelers of all ages can immerse in a solid month of tropical warmth infused holiday magic and merry-making. Here’s a sample:
Wed, Nov 23, pre-sunset: People of all ages gather at Green Street Plaza where it meets Lazy Way Lane for the exciting countdown and 6:00pm official lighting of the Key West Harbor Walk of Lights at the Historic Seaport.
Wed, Nov 23, 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, dazzlingly decorated for the holiday season from Lazy Way Lane at the Green Street Plaza to the Ferry Terminal at Grinnell Street.
Fri, Nov 25, through Christmas Eve, the MARC annual Christmas tree lot: Christmas trees, wreaths, garlands, holiday accessories, ornaments, and wonderful locally produced gifts. More than 1500 trees travel from North Carolina to Key West and are available until they run out or Christmas Eve, which ever comes first. 1401 Seminary Street. For information call the MARC Plant Store at 305-296-9556.
Sun, Nov. 27, 7:00pm, “Messiah” concert at Key West United Methodist Church.
Mon, Nov 28, 5:30pm, City of Key West Tree Lighting Ceremony at Bayview Park.
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.
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.
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, 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.
Sat, Dec 31 – For your 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; the world-famous Red High Heel Drop with Sushi the Drag Queen at the Bourbon St. Pub; the saucy Pirate Wench Drop at the Historic Seaport; and at the Ocean Key Resort, the salty Key Lime Wedge in a Margarita Glass drop, along with live music by Tony Baltimore’s Beatles tribute band.
“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; for more information contact the Lodging Association at 305-296-4959.
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