Key West Holiday Fest offers a magical month of celebration

​Key West Holiday Fest, the southernmost city’s annual island-wide celebration of the season, is set to kick off on Thanksgiving eve, Wednesday, Nov. 27. For a full month, revelers of all ages can experience a plentitude of magical, tropically infused holiday activities and merry-making as only Key West can conceive. Here’s a sampling of what’s ahead:

Wednesday, Nov. 27, pre-sunset: People of all ages, along with Santa and Mrs. Claus, gather at Greene Street Plaza where it meets Lazy Way Lane at the Historic Seaport for the countdown and 6:00pm lighting of the giant “Fishing Buoy” Christmas tree and the Key West Harbor Walk of Lights. At 7:00pm the “Lobster Trap” Christmas tree at Margaret St. Plaza at the Historic Seaport will be officially lit.

Wednesday, Nov. 27, through New Year’s Eve, Key West Harbor Walk of Lights at the Historic Seaport: Explore Lazy Way Lane at the Green Street Plaza to the Ferry Terminal at Grinnell Street while reveling in a wonderland of holiday displays and thousands of lights adorning trees, ships, shops, restaurants and watering holes, adorned in celebration of the season and honoring the maritime history of Key West.

Friday, Nov. 29 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.

Friday, Nov. 29, Black Friday Shopping Extravaganza at Truman Waterfront Park, 10:00am-6:00pm: Join the Key West Artisan Market, the Truman Waterfront Farmers Market and Shop Mom & Pop Key West, artists, crafters, makers and providers offering one of a kind gifts, unique handmade items, exquisite art, along with delicious culinary delights, yummy beverages and exquisite views.

Nov. 29 – 30, Dec 5-6, Fiesta de Navidad, 8:00pm: Get ready for a holiday dance performance extravaganza like no other! Fiesta de Navidad is here to light up your season with beloved holiday characters and incredible Latin dance from salsa to cha-cha-cha. Highlighting the rich cultural influences that make Key West so unique, this show is a high-energy spectacle that will have everyone from kids to grandparents dancing. San Carlos Institute, 516 Duval St.

Sunday, Dec. 1, “Messiah” concert, 7:00pm at Key West United Methodist Church, 600 Eaton Street.

Sunday, Dec. 1, Schooner Wharf Bar 2024 Tree Trimming Party and Toy Drive, from 6:00pm:

Maritime merrymakers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Help decorate the tree and participate in a “Best Handmade Ornament” contest for prizes (bring your own hand-decorated ornament). All tree trimmers will be treated to a free holiday cocktail. Participants are invited to bring an unwrapped gift for the Cheryl Cates Memorial Toy Drive for “Angels Just 4 Kids.” Local authors and artists will be on hand, signing and selling original creations for holiday gift giving.

Monday, Dec. 2, City of Key West Tree Lighting Ceremony, 6:00pm at Bayview Park, 1320 Truman Ave.

Tuesday, Dec. 3, The ReMARCable Decorated Table Top Tree and Wreath Auction takes place at Opal Key Resort, 245 Front St., presented by First Horizon Foundation. Preview at 5:30pm; live auction at 7:00pm.

Thursday, Dec. 5, Pet Pictures with Santa, hosted by All Animal Clinic, 6:00-8:00pm: Pack up Fifi, Fido, and the family and delight in Pet Pictures with Santa at the nautical Christmas tree at the foot of William Street at the Key West Bight Marina/Harbor Walk of Lights. For a cash donation of $25 you’ll receive a professional high resolution digital image. Benefits the Boys & Girls Club of the Keys.

Thursday, Dec. 5, The 11th Annual POSH (Paws Often Steal Hearts) Florida Keys SPCA Fundraiser, 6:00pm, a catered gala event at the Audubon House featuring live dance music raffles, and a silent auction.

Dec. 5-8 and 13-15, Nutcracker Key West: Sugarplum fairies trade tutus for sea fans, and the battle between the mice and the soldiers takes on a whole new flavor. Some 200 local children and adults and 16 professional dancers from New York City will join together in 2024 to produce this outstanding historical recreation of Key West's enchanting version of the Nutcracker ballet at the Tennessee Williams Theatre.

Friday, Dec. 6, 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 Hemingway Social Club at Papa’s Pilar Distillery, the Lighthouse Hotel, Wicker Guesthouse, and the Gardens Hotel. Tickets can be purchased at https://keystix.com/allevents/#holidayhistoricinntour or call 305-296-4959. 

Friday, Dec. 6, Wesley House Family Services Holiday Village and BeLighted Bike Ride at Coffee Butler Amphitheater, 5:00-9:00pm: 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 lighted bike ride 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. 7, Key West Hometown Holiday Parade, 6:30-9:00pm: 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. 8, Monroe County Sheriff’s Office Christmas on the Farm, 1:00-3:00pm: 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. 8: Eaton Street Christmas Stroll, 3:30-7:30pm. Arts and cultural venues and churches unite for this annual community Christmas stroll. Stroll Eaton St. between Whitehead and Simonton, and enjoy stops at venues like Williams Hall for a concert from the Bahama Village Music Program, Tropic Cinema for classic cartoons, The Studios for cocktails and art, and ending at St. Paul’s for a traditional Christmas concert. Admission is free; tickets required and available at https://www.tropiccinema.com/

Dec. 9-10 and 13-23, 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. 9-23, 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. 13, Holiday Historic Inn Tours – Night 2, 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: Key West Butterfly Conservatory, The Mansion on the Sea, Island City House, and The Mermaid & The Alligator. Tickets can be purchased at https://keystix.com/allevents/#holidayhistoricinntour or call 305-296-4959. 

Dec. 13-23 and 26-28, 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, exciting rides, attractions, music and more.

Friday, Dec. 13, Holiday Concert & Bazaar at the Key West Museum of Art & History at the Custom House, 5:00-9:00pm: 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. 14, A Positive Step 5K Rudolph Red Nose Run, 7:00am check-in, 8:00am start time: 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.

Saturday, Dec. 14, Schooner Wharf Annual Key West Lighted Boat Parade, 8:00pm: 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.

Sunday, Dec. 15, 11am-3:00pm, Holiday Classic Car Show: See classic cars from a variety of eras 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. 15 and 22, Christmas Cantata concerts at Fifth Street Baptist Church, 1311 Fifth Street, 11am: The church choir will perform a selection of contemporary music and Christmas carols.

Sunday, Dec. 22, Key West Artisan Market Shop Local Edition, featuring Santa Claus, at Indigenous Park at Higgs Beach, 10:00am-2:00pm: Shop for the holidays at a curated outdoor market offering fine crafts and art from talented Florida Keys makers, a wide variety of food and libations, local musicians and authors, and glorious ocean views along with a visit from old Saint Nick himself.

Tuesday, 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.

Dec. 18-24, Cocoa and Carols: Live Holiday Music Cruise Aboard Schooner America 2.0, 7:00-8:30pm: A festive cruise featuring holiday live music, hot cocoa, cookies, and cheer aboard the beautiful 105-foot Schooner America 2.0.

Wednesday, Dec. 25, Christmas Day Brunch Aboard Schooner America 2.0, 10:00am-12:30pm: A 2.5 hour Christmas Day Brunch with complimentary mimosas, Bloody Mary’s, wine, beer, soft drinks, and H2o. Brunch includes spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudités, and other delicious holiday treats.

Sunday, Dec. 29, City of Key West Menorah Lighting Ceremony, 5:00pm at Bayview Park, 1300 White Street.
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Tuesday, Dec. 31: For your midnight toast, chose between an array of uniquely Key West New Year’s Eve Celebrations, including the world-famous Red High Heel Drop 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 and more.
 
Key West Holiday Fest is presented in part by The Lodging Association of the Florida Keys and Key West and the Monroe County Tourist Development Council. For event links and information, visit www.keywestholidayfest.com or https://tinyurl.com/KeyWestHolidayFest on Facebook. For more information contact the Lodging Association at 305-296-4959.