Key West Holiday Fest Schedule Released
As they do everything, Key West treats the holidays a little differently. That’s why as a Florida resident, you need to experience Key West around the holidays at least once. While we’re on the topic of holidays, St. Augustine has a pretty amazing display as well. But let’s discuss the goings on on the island this season at Key West Holiday Fest.
Key West Holiday Fest begins on Thanksgiving Eve and lasts through New Years.
If you’re planning a trip before the end of 2023, here’s some of the events you can expect to see.
Wednesday, Nov. 22, pre-sunset: People of all ages gather at Greene 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.
Wednesday, Nov. 22, 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.
Friday, Nov. 24, 10:00am-6:00pm: Black Friday Holiday Shopping Extravaganza at the Truman Waterfront mole by the USCGC Ingham Maritime Museum. Fine arts and crafts, jewelry, apparel, produce, delicious foods and more abound at this open-air bazaar.
Monday, Nov. 27, 5:30pm, City of Key West Tree Lighting Ceremony at Bayview Park, 1320 Truman Ave.
Friday, Dec. 1, 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.
Friday, Dec. 1, 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, food trucks, goodies, games, and rides for the kids, and a festive illuminated pedaling party through the streets of Key West, which will depart the Amphitheater at 8:00pm and conclude with a “Best Bike” contest. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House Family Services.
Saturday, Dec. 2, 6:00-9:00pm, 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. 3, 4:30-6:30pm, Santa, Sweets, and Holiday Tree Lighting at the Key West Woman’s Club: Celebrate the season with the Key West Woman’s Club and Mayor Teri Johnston at the beautiful historic Hellings Curry Museum at 319 Duval St. Guests can enjoy appetizers, deserts, Amsterdam eggnog and holiday music performed by the Bahama Village Children’s Choir and the Key West Community Orchestra. Donations of unwrapped, new clothing items for students K-12 appreciated.
Sunday, Dec. 3, 7:00pm, “Messiah” concert at Key West United Methodist Church, 600 Eaton Street.
Dec. 8-12, 15-23, 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. One of the best ways to experience Key West Holiday Fest,
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.
Friday, Dec. 8, Holiday Historic Inn Tours – Night 1, 6:00pm-8:00pm:
Explore four beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings: the Key West Butterfly Conservatory, Wicker Guesthouse, The Mermaid and the Alligator, and the Marquesa Hotel. Tickets can be purchased by calling 305-296-4959 or at KeysTix.com.
Friday, Dec. 8, 5:00-9:00pm, 6th Annual Holiday Concert & Bazaar at the Key West Museum of Art & History at the Custom House: This festive free party features some of Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show. 281 Front Street.
Saturday, Dec. 9, noon-3:00pm: Pet Pictures with The Grinch at the Hard Rock Cafe: Bring your critters for pet pictures with The Grinch. Proceeds benefit River’s Wish, Inc., a 501(c)(3) non-profit senior dog sanctuary.
Saturday, Dec. 9, 10:00am-2:00pm (9:00am check-in), 10th Annual Parade of Paws & Holiday Bazaar at Higgs Beach / Higgs Dog Park: Benefits the Florida Keys SPCA. Costumes encouraged!
Saturday, Dec. 9, 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. Definitely a highlight of Key West Holiday Fest.
Sunday, Dec. 10, 10:00am-3:00pm, Key West Artisan Market’s Holiday Shindig on the Beach: Shop for holiday treasures from local artisans while enjoying live music, tasty treats, fun drinks, activities for the kids – including a ‘snowman’ building contest and even a visit from old St. Nick. Southernmost Beach Resort, 1317 Duval St.
Sunday, Dec. 10, 1:00-3:00pm: Monroe County Sheriff’s Office Christmas on the Farm. The Monroe County Sheriff’s Office invites everyone to come meet the animals during its annual Christmas on the Farm event. 5501 College Road, Stock Island. Donations welcomed!
Sunday, Dec. 10, 5:00pm: City of Key West Menorah Lighting Ceremony
Friday, Dec. 15, Holiday Historic Inn Tours – Night 2, 6:00-8:00pm: Explore four beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings: the Hemingway Social Club at Papa’s Pilar Distillery, Island City House, The Conch House Heritage Inn, and the Lighthouse Hotel. Tickets can be purchased by calling 305-296-4959 or at KeysTix.com.
Friday, Dec. 15 and Saturday, Dec. 16, 8:00pm: Key West Burlesque presents “A Stripmas Carol: Holiday Show Spectacular”, a cheeky burlesque take on the holiday classic for adult audiences. Key West Theater, 512 Eaton St.
Friday, Dec. 15 through Saturday, Dec. 30, Key West Waterfront Winter Wonderland: The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more.
Saturday, Dec. 16, 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 15th 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.
Saturday, Dec. 16, 8:00pm, Fiesta de Navidad Tropical:
Featuring grooves such as salsa, bachata, and cha cha cha, this high energy live performance event presented by the Key West-based Pasión Project studio features World Salsa Champion dancers Carine & Rafael and Mambo royalty Eddie Torres, Jr. with his partner Princess. With live music by Caribe and friends, get ready to move, shake and celebrate all night long, and maybe even dance onstage with the band! Tennessee Williams Theatre.
Sunday, Dec. 17, 11am-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.
Sunday, Dec. 24, 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.
Sunday, Dec. 31: For your midnight toast, chose between an abundance of uniquely Key West New Year’s Eve Celebrations, including the world-famous Red High Heel Drop with Drag Queen Christopher Peterson at the Bourbon St. Pub; the annual “Conch Shell Drop” at Sloppy Joe’s Bar on Duval St.; the “Lowering of the Pirate Wench at Midnight” at Schooner Wharf Bar and Galley at the Historic Seaport, the salty Key Lime Wedge in a Margarita Glass drop and live band at the Ocean Key Resort, and more.
If you’re staying in Southwest Florida for the holidays, there’s a lot going on here, too.