The holidays sparkle with island-inspired seasonal magic as Key West Holiday Fest officially kicks off on Thanksgiving eve, Wednesday, Nov. 25, 2026. For a full month, the island city delights with seaport spectacles, lively markets, enchanting concerts, performances, parades and cherished traditions – all infused with unmistakable Conch Republic charm. Here’s a sampling of what’s in store:
Wednesday, Nov. 25, 5:00pm: Join in the magic of the official lighting of the 21st Annual Key West Harbor Walk of Lights at the Key West Historic Seaport, featuring the lighting of three spectacular themed Christmas trees, a lighted children’s march, holiday music and treats, Santa and Mrs. Claus, merry elves, and lots more. Music begins at 5:00pm at the Greene and Elizabeth St. Plaza, with the giant Fishing Buoy Christmas tree located there illuminated at 6:00pm. 6:15pm brings a Lighted Children’s March down Lazy Way Lane to the lighting of the William St. Nautical tree at 6:30pm. At 7:00pm the famous Key West Lobster Trap tree, located where Margaret St. meets Old Lands End Village, will be illuminated. Attendees are invited to bring a toy to contribute to the Cheryl Cates Toy Drive.
Wednesday, Nov. 25, through New Year’s Eve, the Key West Harbor Walk of Lights at the Historic Seaport Celebrates its 21st Annual Key West “Bight” Before Christmas: Revel in an enchanting 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.
Saturday, Nov. 21 through Christmas Eve, the MARC annual Christmas tree lot: Christmas trees, wreaths, garlands, holiday accessories, ornaments, and wonderful locally produced gifts. More than 1,500 trees travel from North Carolina to Key West and are available until they run out or Christmas Eve, whichever comes first. 1401 Seminary Street.

Friday, Nov. 27, 10:00am-6:00pm, Black Friday Shopping Extravaganza at the Truman Waterfront Park: Discover unique art, original jewelry, handcrafted cards, tropical home décor, specialty foods, local produce, orchids and plants, and treasures made with heart by Florida Keys artists, crafters, and mom-and-pop businesses.
Saturday, Nov. 28, 10:00am-3:00pm, Holiday Makers Market at The Studios of Key West: Every floor of the landmark TSKW building will offer delights and enchantment, from Christmas music and twinkling projections, treasures offered by local artists and artisans, a bar serving up holiday cheer, and more. 533 Eaton Street.
Sunday, Nov. 29, 7:00pm, Händel’s “Messiah” concert performance at Key West United Methodist Church, 600 Eaton Street.
Monday, Nov. 30, 6:00pm, City of Key West Tree Lighting Ceremony at Bayview Park, 1320 Truman Avenue, with a special appearance by Santa Claus.
Tuesday, Dec. 1, The ReMARCable Decorated Table Top Tree and Wreath Auction, 5:30pm preview; 7:00pm live auction: Presented by First Horizon Foundation and hosted by DJ Sanaris at Opal Key Resort, 245 Front Street.
Wednesday, Dec. 2, 13th Annual POSH (Paws Often Steal Hearts) Florida Keys SPCA Fundraiser, 6:00-9:30pm: a gala event at Key West’s Audubon House featuring Vintage Remix Orchestra’s 20-piece band, raffles, food and drinks, and a silent auction.
December, 2-17, “It’s a Wonderful Life: A Live Radio Play,” at the Waterfront Playhouse, 2:00pm on Sunday, Dec. 6 with a Santa after-party; 7:30 pm all other dates. Waterfront Playhouse is transformed into a 1940s radio studio, complete with live Foley effects, a jazz trio, and original jingles created for local Key West businesses. A playful, inventive reimagining of a beloved story that celebrates both theatrical craft and the spirit of the season.
Thursday, Dec. 3, 6:00-8:00pm, 21st Annual Pet Pictures with Santa, hosted by All Animal Clinic: 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 Historic Seaport. For a $25 donation you’ll receive a professional high-resolution digital image. Benefits the Boys & Girls Club of the Keys.
December, 3-7, Nutcracker Key West, Sat./Sun. 1:00pm; Thurs./Fri., Sun/Mon 7:00pm: 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 The Tallahassee Ballet will join together in 2026 to produce this outstanding historical recreation of Key West’s enchanting version of the Nutcracker ballet at the Tennessee Williams Theatre.

Friday, Dec. 4, 5:00-9:00pm, Wesley House Family Services Holiday Village and BeLighted Bike Ride at Coffee Butler Amphitheater: Celebrate with Santa Claus, carnival rides, bounce houses, community booths offering games and activities, performances, food vendors and even snow! The beloved BeLighted bike ride departs the Amphitheater at 8:00pm. Admission benefits Wesley House Family Services.
Saturday, Dec. 5, 10:00am-1:00pm, Print Your Own Holiday Cards: Kids Edition with Bria Ansara: Kids aged 8-14 can create a set of cheerful handmade holiday cards using kid-friendly printmaking techniques during this Kat in the Hat Classroom event at The Studios of Key West.
Saturday, Dec. 5, 7:00pm, Key West Hometown Holiday Parade: Spectators line the streets for the homegrown parade that kicks off at Bayview Park and travels along Truman Avenue and Duval Streets with festooned floats and marching groups consisting of adults, children, and elves, along with assorted hoofed and whiskered friends.
Saturday, Dec. 5, 12:00pm-4:00pm, Key West Woman’s Club European-Style Holiday Market: Enjoy an open-air European-style holiday shopping experience at the beautiful historic Hellings Curry Museum, 319 Duval Street.
Sunday, Dec. 6, Eaton Street Stroll, 3:00-6:00pm: Keys Choral Arts invites revelers to stroll Eaton Street and nearby locales, beginning with a live Nativity and concert at the Old Stone Church, 600 Eaton Street, followed by festive visits to multiple local galleries, shops and landmarks. Keys Choral Arts will also present two performances at Williams Hall during the event. Free to attend.
Sunday, Dec. 6, 4:30pm, Community Open House and Holiday Tree Lighting at the Key West Woman’s Club: Celebrate with the Key West Woman’s Club at the beautiful historic Hellings Curry Museum, 319 Duval Street. Guests can enjoy appetizers, desserts, Amsterdam eggnog and holiday music. Donations of unwrapped, new clothing for students K-12 appreciated.
Sunday, Dec. 6, 5:00-6:00pm, City of Key West Menorah Lighting Ceremony: The annual ceremony, held at Bayview Park, 1320 Truman Avenue, marks the beginning of Hanukkah, the eight-day Jewish Festival of Lights.
Sunday, Dec. 6, 6:00pm-until it’s over, Schooner Wharf Bar Tree Trimming Party and Toy Drive: Maritime merrymakers can help decorate the tree and make dreams come true at the popular waterfront winter wonderland. Participants are invited to bring an unwrapped gift for this year’s holiday toy drive.
Monday, Dec. 7 through Sunday, Dec. 27, Old Town Trolley Holiday Lights & Sights Tours: Multiple nightly tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.
Tuesday, Dec. 8 through Sunday, Dec. 27, 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. (No tours the night of the Key West High School Winter Concert).
Friday, Dec. 11, 5:00-8:00pm, 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 projected onto the façade of the historic Custom House, 281 Front Street.
Friday, Dec 11, 6:00-8:00pm, Holiday Historic Inn Tours – Night 1: Visit and tour four beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings. Tickets available beginning Nov. 16; visit KeysTix.com or call 305-296-4959 prior to the tour date to purchase.
Saturday, Dec. 12, 7:00am check-in, 8:00am start time, 18th A Positive Step 5K Rudolph Red Nose Run: Don your festive holiday jammies and join in the Rudolph Red Nose 5K, starting and ending at the Southernmost Beach Café. Runners and walkers of all ages and abilities are welcome; registrants receive a collectable race bag, free t-shirt, and commemorative cup.
Saturday, Dec. 12, 6:00-8:00pm: December Duo Holiday Concert at The Studios of Key West: Violinist Irie Monte will be joined by Crispin Campbell on cello for an evening of string music on the rooftop of the landmark historic building on Eaton Street.
Saturday, Dec. 12, 8:00pm, Schooner Wharf Annual Key West Lighted Boat Parade:Arrive at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights before the glittering parade of illuminated watercraft begins.
Saturday and Sunday, Dec. 12 and 13, visit with Santa at the Shops at Mallory Square, 1:00-3:00pm: The Key West Cooking Show is hosting Santa Claus at the historic building at 291 Front Street. Bring the kids and/or furry friends along with your own camera to capture picture-perfect island-style holiday photos with Santa.
Sunday, Dec. 13, 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!
Tuesday, Dec. 15, 7:00pm, Keys Choral Arts Winter Concert at the Basilica of St. Mary, Star of the Sea: Keys Choral Arts will present their annual winter concert with a program featuring new settings of traditional Christmas music. 1010 Windsor Lane. Free to attend. Reception to follow the concert.
Thursday, Dec. 17, 1:00-6:00pm, Kris Kringle Mart at Truman Waterfront Park: Discover artisan goods, handcrafted items, festive décor, delicious holiday treats and seasonal cheer at the Kris Kringle Mart at the Truman Waterfront Farmers Market.
Thursday, Dec. 17, 6:00-8:00pm, Holiday Walk on White Art Stroll: One of Key West’s most popular ongoing art stroll experiences presents local painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers and their works, along with performances, demonstrations, and food and libation samples at select locations along White Street and vicinity.
Friday, Dec. 18, 6:00-8:00pm (5:30 check-in), Holiday Historic Inn Tours – Night 2: Visit and tour four beautifully decorated locations and their unique architecture and history while enjoying light sweet and savory holiday treats and libation samplings. Tickets available beginning Nov. 16; visit KeysTix.com or call 305-296-4959 prior to the tour date to purchase.
Saturday, Dec. 19, 11:00am-2:00pm: The Key West Harry S. Truman Foundation’s Great Gingerbread Build: Held on the grounds of the Harry S. Truman Little White House, guests will be provided with gingerbread crackers, icing and a plethora of candies for gingerbread house building. A limited number of kits will also be available. Free and open to merry-makers of all ages.
Saturday and Sunday, Dec. 19 and 20, visit with Santa at the Shops at Mallory Square, 1:00-3:00pm: The Key West Cooking Show is hosting Santa Claus at the historic building at 291 Front Street. Bring the kids and/or furry friends along with your own camera to capture picture-perfect island-style holiday photos with Old Saint Nick.
Sunday, Dec. 20, 10:00am-2:00pm, Key West Artisan Market “Holiday Shop Local” edition with special guest, Santa Q: A curated outdoor Holiday market at Indigenous Park at Higgs Beach will offer fine crafts and art from talented Florida Keys makers, a wide variety of festive food and libations, music, local authors and glorious ocean views, along with a visit from Santa Q himself.
Sunday, Dec. 20, 4:00pm: Key West Sunset Celebration is throwing a Winter Solstice Party. Join artists, food vendors, and performers at Mallory Square for family-friendly activities including photos with Santa, decorating a Christmas tree sculpture with palm fronds and wish lanterns, and a world record attempt for the most snowflakes drawn with sidewalk chalk! The party starts two hours before sunset. https://www.sunsetcelebration.org/
Monday, Dec. 21 through Thursday, Dec. 24, Cocoa and Carols Christmas Holiday Lights Cruise aboard Schooner America 2.0: Holiday spirit abounds during his 1.5 hour cruise aboard the festively decorated 105-foot sailing vessel, where revelers of all ages can sing Carols with the band while enjoying hot cocoa and holiday cookies. Full bar and snacks also available for purchase.
Friday, Dec. 25, 10:00am-12:30pm, Christmas Day Brunch Sail Aboard Schooner America 2.0: This 2.5 hour excursion features a brunch with spiral ham, meats and cheeses, bagels and pastries, smoked salmon, crudités, quiche, and other delicious Christmas day treats, along with champagne, wine, beer and soft drinks.
Thursday, Dec. 31: For your midnight toast, choose between an abundance 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 at the Historic Seaport, 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. Event details are subject to change. For links, updates and information, visit www.KeyWestHolidayFest.com or https://tinyurl.com/KeyWestHolidayFest on Facebook. For more information contact the Lodging Association at 305-296-4959.
Pack up Fifi, Fido and your favorite peeps for this year’s Pet Pictures with Santa event, taking place Thursday, Dec. 3 at Key West’s historic seaport. (Photo: Carol Tedesco/Key West Holiday Fest)






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