Sunshine, Santa and Seasonal Cheer: Key West Holiday Fest Kicks off November 26

The holidays take on a tropical glow as Key West Holiday Fest officially kicks off on Thanksgiving eve, Wednesday, Nov. 26, 2025. For a full month, the island city sparkles with seaport spectacles, festive markets, musical moments, parades and cherished traditions – each wrapped in unmistakable "Conch Republic" charm. Here’s a sampling of what’s in store:

Wednesday, Nov. 26, pre-sunset: Join the countdown and 6:00pm lighting of the giant “Fishing Buoy” Christmas tree and the Key West Harbor Walk of Lights at the Key West Historic Seaport, located at Greene Street Plaza where it meets Lazy Way Lane. At 7:00pm the “Lobster Trap” Christmas tree at Margaret St. Plaza will be officially lit. Santa’s helpers are invited to bring a toy to contribute to the Cheryl Cates Toy Drive.

Wednesday, Nov. 26, through New Year’s Eve, the Key West Harbor Walk of Lights at the Historic Seaport Celebrates its 20th 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.

Friday, Nov. 28 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.

Friday, Nov. 28, 10:00am-6:00pm, Black Friday Shopping Extravaganza: Join the Key West Artisan Market, Truman Waterfront Farmers Market, and Mom & Pop Key West vendors at the Truman Waterfront Park for a one-of-a-kind outdoor Black Friday shopping event, offering handmade treasures, original art, tasty eats, and island drinks.

Saturday, Nov. 29, 10:00am-3:00pm, Holiday Makers Market at The Studios of Key West: Discover holiday delights on every floor of the landmark TSKW building, from treasures offered by local artists and artisans, a DIY ornament painting area with paint, glitter and craft supplies, Christmas music and twinkling projections, a bar serving up holiday cheer, and plenty more. 533 Eaton Street.

Sunday, Nov. 30, 5:30pm, City of Key West Tree Lighting Ceremony at Bayview Park, 1320 Truman Ave., with a special appearance by Santa Claus!

Sunday, Nov. 30, 7:00pm, “Messiah” concert at Key West United Methodist Church, 600 Eaton Street.
Tuesday, Dec. 2, The ReMARCable Decorated Table Top Tree and Wreath Auction hosted by DJ Sanaris 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. 4, 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 16’ 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. 4, 11th Annual POSH (Paws Often Steal Hearts) Florida Keys SPCA Fundraiser, 6:30-9:30pm at the Audubon House, a catered gala event featuring live dance music, raffles, and a silent auction.

Friday, Dec. 5, 5:00-9:00pm, 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, unlimited carnival rides, more than 20 community booths offering free kids’ activities, community performances, food vendors and even snow!  The annual lighted bike ride will depart the Amphitheater at 8:00pm and conclude with an official after party at Hanks’s Hair of the Dog Saloon. Admission benefits Wesley House Family Services.

Saturday, Dec. 6, 7:00-10:00pm, 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.

Saturday, Dec. 6, 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 at 319 Duval St.

Sunday, Dec. 7, Eaton Street Stroll: Stroll the blocks between Whitehead and Simonton Streets and enjoy an afternoon of magical holiday cheer featuring festive performances by local choirs, unique gifts and art at local galleries and holiday hospitality. Admission is free; tickets required.

Sunday, Dec. 7, 3:30-6:30pm, Community Open House and Holiday Tree Lighting at the Key West Woman’s Club: Celebrate the season with the Key West Woman’s Club 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. 7, 6:00pm, Schooner Wharf Bar Tree Trimming Party and Toy Drive: 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). Participants are invited to bring an unwrapped gift for “Angels Just 4 Kids” and “Toys for Tots.

Dec. 8 and Dec. 11-23, 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.

Friday, Dec. 12, Holiday Historic Inn Tours – Night 1, 6:00-8:00pm (5:30 check-in): Explore beautifully decorated locations and their unique architecture and history in the company of fellow holiday revelers while enjoying light sweet and savory holiday treats and libation samplings: The Gardens Hotel, Island City House, Key West Cooking Show and the Lighthouse Hotel. Tickets can be purchased by calling 305-296-4959 or at KeysTix.com.

Friday, Dec. 12, 5:00-9:00pm, 7th 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. 13, 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; registrants receive a free t-shirt.

Saturday, Dec. 13, 11:00am-2:00pm: The Key West Harry S. Truman Foundation’s Great Gingerbread Build: 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, Dec. 13, Pet photos with Santa at Hank’s Hair of the Dog Saloon, 12:00-4:00pm: Fun for people and pets includes Santa visits, raffles and a costume contest. 409 Caroline St.

Saturday, Dec. 13, 4:00-8:00pm, Merry Marketplace: Celebrate the holidays island-style at the Southernmost Beach Resort with live music, local art, handmade gifts, tasty treats, cocktails, and kid-friendly fun. Activities include an open pool, crafts, Santa’s arrival, and the unforgettable Christmas Queen Pageant. 508 South St.

Saturday, Dec. 13, 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.

Sunday, Dec. 14, 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. 14, 5:00-7:30pm, City of Key West Menorah Lighting Ceremony at Bayview Park, 1300 White St.
Tuesday, Dec. 16, 6:30pm, “An Evening Aglow: A Candlelight Christmas with Marjory Lee” at the Key West Theater: Celebrate the season with a full band Christmas concert bringing classic holiday hits with Marjory Lee, Jeff Bateman, Tim Conroy, Henry Lysy Jr., and Hiram Garzaro, along with surprise guests. Before the show there will be Classic Santa Photos with photographer Nick Doll and a mini market with local vendors. 512 Eaton St.

Thursday, Dec 18, 6:00-9:00pm, The Holiday Walk on White Art Stroll: Just in time for last minute holiday shopping, Walk on White, 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. White St. from Southard to United.

Fri, Dec 19, 6pm – 8pm (5:30 check-in) Holiday Historic Inn Tours – Night 2: Visit and tour 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, Wicker Guesthouse and The Mermaid & the Alligator. Tickets available beginning Nov. 15; visit KeysTix.com or call 305-296-4959 prior to the tour date to purchase.

Dec 19-24, 7:00-8:00pm and 1:30-3:00pm on select dates, Cocoa and Carols: Live Holiday Music Cruise Aboard Schooner America 2.0: A Festive Christmas cruise featuring live holiday music, hot cocoa, cookies and treats. keywestchristmas.org

Sunday, Dec. 21, 10:00am-2:00pm, Key West Artisan Market “Shop Local, Support 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 food & libations, music, local authors and glorious ocean views, along with a visit from old Saint Nick himself.

Sunday, Dec. 21, 11:00am-3:00pm, The Florida Keys Southernmost Car Club Holiday Classic Car Show and Toy Drive: 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.

Thursday, Dec. 25, Christmas Day Brunch Sail Aboard Schooner America 2.0, 10:00am-12:30pm: This 2.5 hour excursion features complimentary mimosas, Bloody Mary’s, wine, beer, soft drinks, and water. Brunch includes spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudités, and other delicious Christmas day treats. 

Wednesday, 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 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.