From Nov. 23 through New Year’s Eve, the Key West Harbor Walk of Lights at the Historic Seaport offers a wonderland of light-bedecked palm trees, Christmas trees, ships, shops, restaurants and watering holes. CAROL TEDESCO/

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:

Wednesday, Nov. 23, pre-sunset: People of all ages gather at Greene Street Plaza, where it meets Lazy Way Lane for the countdown and 6 p.m. official lighting of the Key West Harbor Walk of Lights at the Historic Seaport. 

Wednesday Nov. 23, through New Year’s Eve, Key West Harbor Walk of Lights at the Historic Seaport: Lighted palm trees, Christmas trees, ships, shops, restaurants and watering holes.

Friday, Nov. 25, through Christmas Eve, the MARC annual Christmas tree lot: Christmas trees, wreaths, garlands, accessories, ornaments and gifts. More than 1,500 trees are available until they run out or Christmas Eve, whichever comes first. 1401 Seminary St. 

Sunday, Nov. 27, 7 p.m. “Messiah” concert at Key West United Methodist Church. 

Monday, Nov. 28, 5:30 p.m., City of Key West Tree-Lighting Ceremony at Bayview Park.

Friday, Dec. 2, 4-8 p.m. Wesley House Family Services Holiday Village & BeLighted Bike Ride at Coffee Butler Amphitheater: A family-friendly party with Santa Claus, music, games, food trucks, goodies. Admission fee benefits Wesley House Family Services. Bike ride through the streets departs at 8 p.m. 

Saturday, Dec. 3, 11am-2pm, Pet Pictures with The Grinch at Hank’s Hair of the Dog Saloon, 409 Caroline St.  Proceeds benefit River’s Wish, Inc., a non-profit senior dog sanctuary. 

Saturday, Dec. 3, 7 p.m. Key West Hometown Holiday Parade kicks off at Bayview Park and travels along Truman Avenue and Duval Street.

Sunday, Dec. 4, 6-8 p.m. 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: Sixty local children and adults and 15 professional dancers present this recreation of Key West’s 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 depart from Key West High School and convey caroling passengers through streets and neighborhoods to revel in the illuminated city of Key West.

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

Friday, Dec. 9, Holiday Historic Inn Tours – Night 1, 6-8 p.m.: Tour four decorated island locales: Key West Butterfly Conservatory, The Mermaid & the Alligator, Winslow’s Bungalows, and Weatherstation Inn.

Friday, Dec. 9, 5-9 p.m. 5th Annual Holiday Concert & Bazaar at Custom House Museum features local artisans, musicians and choirs, along with a holiday light show. 

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

Saturday, Dec. 10, 8 p.m. Schooner Wharf Annual Key West Lighted Boat Parade. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the Key West Harbor Walk of Lights.

Saturday, Dec. 10 and Friday, Dec. 16, Visit Santa at the North Pole, 12-2 p.m.

at the Southernmost “North Pole,” upstairs at the Shops at Mallory Square, 291 Front St. Letter-writing stations and a mailbox will be available for the younger set. 

Friday, Dec. 16, Holiday Historic Inn Tours – Night 2, 6-8 p.m. Tour four decorated island locales: Hemingway’s Library @ Papa’s Pilar Distillery, The Marquesa Hotel, The Gardens Hotel and Island City House. 

Saturday, Dec. 17, 7 a.m. check-in, 8 a.m. start, A Positive Step 5K Rudolph Red Nose Run starting and ending at the Southernmost Beach Café, 1405 Duval St. Don your festival holiday jammies. Runners and walkers of all ages and abilities are welcome; first 100 registrants receive a free t-shirt. 

Sunday, Dec. 18, 11 a.m. to 3 p.m., Holiday Classic Car Show at the Conch Republic Seafood Co. parking lot at the corner of Greene and Elizabeth streets. Bring an unwrapped toy for the Monroe County Domestic Abuse Shelter.

Sunday, Dec. 18, 5 p.m. City of Key West Menorah Lighting Ceremony at Bayview Park.

Dec. 25, Holiday Jazz in the Gardens, 5-7 p.m. The Gardens Hotel, 526 Angela St. hosts outdoor jazz in its garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly.
Saturday, Dec. 31 – For your midnight toast, chose from an abundance of uniquely Key West New Year’s Eve Celebrations: The Conch Shell Drop at Sloppy Joe’s Bar on Duval Street; the Red High Heel Drop with Sushi the Drag Queen at Bourbon St. Pub; the Pirate Wench Drop at the Historic Seaport; and the Key Lime Wedge in a Margarita Glass drop at Ocean Key Resort.

Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.