The lighting of the Harbor Walk of Lights on Wednesday, November 24 marks the start of Key West Holiday Fest revelries that take place across the island city through New Year’s Eve. (Photo: Carol Tedesco/Key West Holiday Fest)

Cayo Hueso is Merry, Bright and ready for Key West Holiday Fest 2021

Key West Holiday Fest is ready to sparkle and shine in all its glory in 2021, beginning with the official lighting of the Key West Harbor “Walk of Lights” at the Historic Seaport on Wednesday, November 24. Music starts at 5:00pm near the fishing buoy ball themed Christmas tree at the corner of Greene and Elizabeth Streets; the lights come on at 6:00pm – and festivities continue through December 31, with highlights including (but not limited to):

Wednesday, November 24 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.

Wednesday, November 24, Holiday Open House at the catamaran Argo Narvis, docked at the Historic Seaport, 5:00-8:00pm: Revelers of all ages and their pets are invited to stop by and enjoy snacks, libations, selfie pictures with “Santa Q-Mitch,” and a showing at dark of “It’s a Wonderful Life” projected onto the sails of the Argo Narvis.

Monday, November 29, City of Key West Tree Lighting Ceremony, 6:00pm at Bayview Park.

Tuesday, November 30, Lighting of the Menorah, 5:30pm at Bayview Park.

Friday, November 26 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.

Wednesday, December 1- 25, Historic Tours of America Holiday Lights & Sights Home Decorating Contest: Spectators can enjoy the spectacle while residents from Key West to Key Haven enter HTA’s competition for the most beautifully decorated house on the block, with public votes determining the winners. Cash prizes awarded for First, Second, and Third place.

Wednesday, December 1, 6:00-9:30pm: 8th Annual POSH (Paws Often Steal Hearts) fundraising event for the Florida Keys SPCA: A catered gala-style affair at the Audubon House & Tropical Gardens with live music, silent auction, raffle prizes, delicious food, and lovely libations.

Thursday, December 2 through the Holidays at Fort West Martello Tower:

The Key West Garden Club, stewards of the Civil War era property, deck out the magnificent Fort and surrounding grounds and gardens with luscious holiday decorations and lights. Open from 9:30am to 2pm daily at 1100 Atlantic Ave., admission is free; donations cheerfully accepted. Much of the festive décor will be visible at nighttime for walking, biking and drive-by enjoyment.

Friday, December 3, Pet Pictures with Santa, 6:00pm-8:00pm: 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, December 3, 4:00-8:00pm: Wesley House Family Services BeLighted Bike Ride and Holiday Village at Coffee Butler Amphitheater: Celebrate the holidays in good cheer with a Belighted Bike Ride through the streets of Key West, preceded by a family friendly pre-party with Santa Claus, music, crafts, games, food trucks, goodies for the kids, and a “Best Bike” contest. Admission fee includes Holiday Village and Bike Ride, and benefits Wesley House. Bike ride departs at 8:00pm.

Saturday, December 4, Key West Hometown Holiday Parade, 7:00pm: Delighted 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, December 4, 11, and 18, plus Sunday, Dec. 19, and Friday December 24, Visit Santa at the North Pole, 11:00am-3:00pm: Kids of all ages can visit with Santa at the Southernmost “North Pole,” conveniently located in the upstairs level of the historic Shops at Mallory Square, 291 Front Street. Sit with Santa or have a socially distanced visit. Letter writing stations and a mailbox will be available for the younger set.

Sunday, December 5, Holiday Classic Car Show, 11:00am-3:00pm: See classic cars from a variety of eras at the official show of the Florida Keys Southernmost Car Club, and chose 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, December 5, Eaton Street Christmas Stroll, 4:00pm start time: The family-friendly holiday event begins at St. Paul’s Episcopal Church and continues to the Old Stone United Methodist Church, The Tropic Cinema for a classic Christmas short film, the Studios of Key West, Key West Theater, and Williams Hall. Revels will include music performed by Keys Choral Arts, Mateo Jampol, and other local performers, with some sweet treats along the way. Admission is free but tickets are required and are available at Key West Theater box office and secureboxoffice.com.

Friday, December 10, Annual Holiday Concert & Bazaar at Custom House Museum, 5:00-9:00pm: This festive free party features Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show.

Friday, December 10, Holiday Historic Inn Tours – Night 1, 6:00-8:00pm: Explore some of the most romantically decorated locales on the island, including the Key West Butterfly Conservatory, the Gardens Hotel, Island City House, and Amsterdam’s Curry Mansion.  Arrive at each property via free trolley or your own transportation and explore its unique architecture, history and holiday ambiance while tasting sweet and savory holiday treats and libation samplings.

Saturday, December 11, Annual Parade of Paws & Holiday Bazaar at Higgs Beach / Higgs Dog Park, 10:00am-2:00pm (9:00am check-in): – Benefits the Florida Keys SPCA. Costumes encouraged!

Saturday, December 11, Schooner Wharf 30th Annual Key West Lighted Boat Parade, 8pm: 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 with its array of shops, restaurants and watering holes, charmingly decorated for the holidays.

Sunday, December 12-17, 20-23, and Dec 26: Conch Tour Train Holiday Lights Tours: Twice nightly tours convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

Sunday, December 12-17, 20-23, and Dec 26: Old Town Trolley’s Holiday Lights and Sights Tours: Twice nightly tours convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

December 15-17, Sugar Rum Cherry: A Burlesque Nutcracker: Put on your stockings and pull out your sugarplums for this naughty but nice holiday 2-act reverie at Key West Theater that features a bevy of burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic.

Friday, December 17, Holiday Historic Inn Tours – Night 2, 6:00-8:00pm: Explore some of the most romantically decorated inns on the island, including: The Mermaid & the Alligator, Winslow’s Bungalows, Wicker Guest House, and the Weatherstation Inn.

Saturday, December 18

Don your festive holiday jammies and join in the 13th A Positive Step 5K Rudolph Red Nose Run – the PJ Edition, taking place Saturday morning, December 18, starting and ending at the Southernmost Beach Café, 1405 Duval Street, Key West. Runners and walkers of all ages and abilities are welcome to participate; first 100 registrants receive a free t-shirt.

Friday, December 24-26, Holiday Jazz in the Gardens, 5:00-7:00pm: The Gardens Hotel at 526 Angela street welcomes holiday-goers to festive outdoor jazz performances in its famous garden, with a full cash bar on site.

Saturday, December 25, SV Argo Narvis Christmas Brunch, 11:00am-1:00pm: Christmas morning brunch on board the luxury catamaran sailing yacht will include delectable fare from top Key West restaurants along with bottomless mimosas, premium wine and craft beers, eggnog, juices, coffee, and award-winning Bloody Mary’s from the Saint Hotel. Limited to 24 passengers.

Tuesday, December 31 – For your midnight toast, chose between an abundance of uniquely Key West New Year’s Eve Celebrations, including the Conch Shell Drop at Sloppy Joe’s Bar on Duval Street and the world-famous Red High Heel Drop at the Bourbon St. Pub.

“Key West has its own beautiful and unique tropical holiday magic, with an abundance of festive activities taking place both in and out-of-doors, and most in easy walking and biking distance from one another,” commented Jodi Weinhofer, President of the Lodging Association of the Florida Keys and Key West. From lighted parades on land and sea, to enchanting inn tours, to holiday themed burlesque shows and New Year’s Eve extravaganzas, there’s something wonderful for all ages happening here.”

Key West Holiday Fest 2021 is presented by Berkshire Hathaway Keys Real Estate, Opal Key Resort & Marina, Old Town Trolley Tours and Conch Tour Train, Shops at Mallory Square, The Lodging Association of the Florida Keys and Key West, and the Monroe County Tourist Development Council. For links to all events, visit www.KeyWestHolidayFest.com. For more information, contact the Lodging Association at 305-296-4959.

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