Key West ``Bight`` before Christmas Celebration
Scroll down for two Holiday Calendars
Escape to that Southernmost Holidays Spirit, Before Christmas!
The Harbor Walk of Lights
Lighting up every evening through New Year’s Eve.
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View Two Complete Holiday Event Calendars Below
2019 Key West “Bight” before Christmas
Waterfront Schedule of Events
(2nd Islandwide Calendar Further Down)
Check back often for Updates!!
Kick off the holiday season in Key West!
Wednesday, Nov. 27
Lighting of the Key West “Harbor Walk of Lights”™
FREE 6:00pm – More lights and animated displays than ever!
LOCATION: Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the … 2019 Key West “HarborWalk of Lights”… with more lights and creative displays than last year, all continuing the “Maritime History of Key West” theme.
The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the Fishing Buoy Tree, a fresh pine Nautical Christmas Tree and the original Key West Lobster Trap Tree.
The entire length of the “Harbor Walk of Lights” runs along water past Greene St, William St, Margaret St and all the way to the Key West Ferry Terminal.
So there’s plenty to see along the way for a merry infusion of holiday lights and nautical displays, including ship’s anchors, tropical birds, tropical fish, flamingos, Pelicans, manatees, animated sea turtles and dolphins, and even a festive moray eel.
Along with more lights and lighted palm trees than ever, the 2019 holiday season at the Key West Historic Seaport is adding up to be spectacular!
And don’t forget that the Harbor Walk is full of places for unique holiday gift shopping, including original artwork, clothing, jewelry and gift certificates for watersports. Come feel the Holiday spirit on the waterfront and enjoy great dining (from casual to a culinary masterworks) and some of the most famous Key West watering holes for holiday cocktails and great live music.
The Harbor Walk of Lights lights up every evening at dusk, all the way through New Year’s eve!
Friday, Dec. 6
Pet Pictures with Santa™ – Hosted by The All Animal Clinic
FREE to attend. 6:00 – 8:00pm – Photos by Rob O’Neal
LOCATION: Look for Santa at the Nautical Christmas Tree at the foot of William St. on the HarborWalk of Lights. Santa pics with the pets and kids, treats for all! Pics are $20 (cash only) to benefit the Boys & Girls Club. Get professional furry family photographs for that special holiday card this year!
Saturday, Dec. 7
Key West City “Hometown Holiday Parade”
FREE 7:00pm
LOCATION: Viewing starts on Truman Ave. (at White St.) then proceeds down to Duval St., then down Duval St.ending at Eaton St.
The most charming hometown parade you’ll ever see with holiday floats, and tons of kids of all ages. Of course Santa will make a guest appearance!
Saturday, Dec. 14
Schooner Wharf Bar & Galley
29th Annual Key West Lighted Boat Parade
FREE • Parade starts at 8:00pm
LOCATION: Viewing all along the Harbor Walk of Lights at the Historic Seaport.
Reviewing stand is at the Schooner Wharf Bar and Galley. Come early for great shopping, live holiday music performance, dinner and drinks.
Click below – SEE HOW TO ENTER YOUR BOAT!
Sunday, Dec.15
Conch Republic Seafood “Holiday Classic Car Show”
FREE • 11:00 – 3:00pm
LOCATION: Conch Republic Seafood Company – Greene & Elizabeth St.
Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter.
VOTE for the “Peoples Choice” award
Awards for: BEST engine, interior, original & custom, Best in Show
See classic cars from every era decked out for the holidays!
Florida Keys Southernmost Car Club
Non-member cars may enter same day FREE with an unwrapped toy!
Saturday, Dec. 21
“Violins in Motion”
Children’s Group Performance of Holiday Music!
Collecting donations for JDRF and Juvenile Diabetes Research
FREE 6:30 – 8:00pm
LOCATION: On the Harbor Walk of Lights under the “Fishing Buoy Christmas Tree”, at Green and Elizabeth St.
A holiday musical performance by budding musicians from 6 to 18 years old – for a sweet dose of Christmas spirit.
AND ALWAYS GREAT SHOPPING, WATERSPORTS, DINING AND HOLIDAY LIBATIONS ON THE KEY WEST “HARBOR WALK OF LIGHTS”, THROUGH THE NEW YEAR!
TBA
Key West Holiday Historic Inn Tour
6:00 – 8:00pm • Call (305) 296-4959
Key West is known for its beautiful historic inns, and the Holiday Historic Inn Tour is the perfect way to visit these magnificent properties decorated for the season, featuring art, fine food from top local restaurants and holiday libations at each stop. This years inns are:
- First Night: The Gardens, Island City House, Curry Mansion, Weather Station, The Butterfly Conservatory
- Second Night: Hemingway Rum Co. Distillery, Old Town Manor, Wicker House, The Mermaid & The Alligator, Sweet Dreams, Santa Maria
TBA
Key West Lighted Bike Ride
For Holiday Helpers Toy Drive & holiday fun! 7:00pm – The ride is a family event beginning with a registration / check-in at 6 p.m. for with Helmet fitting and Santa Claus visit.
Families and individuals with lighted and decorated bikes ride through the streets for the community to see.
Registration for the ride is one unwrapped toy for the Key West Holiday Store and Wesley House Family Services.
TBA
Conch Tour Train Holiday Lights Tours
Join the Conch Tour Train for their annual holiday lights tour of the island. To get things started we will serve up some holiday cheer with cider and cookies. Then it is all aboard for an hour tour that takes you to all of the island’s most elaborately decorated houses, buildings and neighborhoods and caroling. Call 305-294-5161 for reservations and information.
TBA
Old Town Trolley Holiday Lights and Sights Tour
Celebrate the season aboard Old Town Trolley on their Holiday Lights and Sights Trolley. There won’t be a white Christmas in Key West, but that doesn’t stop the island from decking the halls with lights and decorations. Call 305-296-6688 for reservations and information.
TBA
2018 Nutcracker Key West
Set to the enchanting music of Tchaikovsky, the Nutcracker Key West, produced bi-annually, is the largest community production brought to the stage in Key West.
This year, 60 of our community’s children and adults along with 15 professional dancers from around the world will join together again to produce this outstanding historical recreation of Key West’s version of the Nutcracker, Nutcracker Key West.
TBA
Christmas on the Sheriff’s Animal Farm
From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff’s Office Animal Farm is situated at the county’s detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff’s Animal Farm is open the second and fourth Sundays of the month. Call 305-293-7300.
TBA
“Sugar Rum Cherry: A Burlesque Nutcracker”
Put on your stockings and pull out your sugarplums for Key West Burlesque’s “Sugar Rum Cherry: A Burlesque Nutcracker” on Thursday, December 14 through Saturday, December 16 at Key West Theater, 512 Eaton Street. This naughty holiday two-act reverie features your favorite local performers, international burlesque superstars, and amazing aerial acrobats as they visit the land of libations. Doors open at 7:30p.m., show starts at 8:00p.m. Sponsored in part by the Monroe County Tourist Development Council. Call 305.985.0433.
TBA
2nd Annual Parade of Paws & Holiday Bazaar
Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends. Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet’s photo! Holiday Bazaar inside the dog park features entertainment, food vendors, photos with Santa, gifts for that special person on your list and more! A unique opportunity to support the lifesaving mission caring for the Keys’ community’s homeless animals, the event supports the Florida Keys SPCA. Call 305-294-4857.
TBA
Third Annual Custom House Holiday Concert & Bazaar
The Key West Art & Historical Society hosts the third annual event, 5-9 p.m., at the historic Custom House Museum, 281 Front St. Highlights are to include performances by musicians and choirs, local artisans showcasing their wares, a light show and “selfies” with Santa. Open and FREE to the public. Call 305-295-6616.
TBA
Holiday Jazz in the Gardens
5:30 to 8:00 pm. FREE.
Festive outdoor jazz performance at the Gardens Hotel. Cash bar & large wine selection.
TBA
59th Annual Key West House and Garden Tour
Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-7 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $30 in advance, $35 day-of-tour. Proceeds benefit the foundation’s museum and programs. Call 305-294-9501.
TBA
Annual Key West Dachshund Walk
Frost-free Key West becomes a “wiener wonderland” when about 200 dachshunds and their owners take a noontime New Year’s Eve stroll through the island’s picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.
Dec. 31, 2019
Key West New Year’s Eve Celebrations
- Rooftop Conch Shell Drop – at Sloppy Joe’s, 305-296-2388
- Drag Queen Drop in a giant Red High Heal – at Bourbon St Pub, 305-293-9800
- Pirate Wench down the Schooner mast – at Schooner Wharf Bar, 305-292-3302
- Key Lime Wedge drop into giant Margarita – at the Ocean Key Resort, 305-296-7701
Park in the Main Parking Lot located at Margaret & Caroline St. OR the Parking Garage one block away at Caroline & Grinnell St. OR in the lot at Green & Elizabeth St.
Please use FREE scooter parking areas and designated bike racks all around the Historic Seaport and Harbor Walk Area. Please no locking bikes to the decorations!
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KW “Bight” Before Christmas.
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Photos by Rob O’Neal
