Escape to that Southernmost Holidays Spirit, Before Christmas!

The Harbor Walk of Lights

Lighting up every evening through New Year’s Eve.

A Nautical theme honoring the maritime history of the Key West waterfront.

The “Harbor Walk of Lights” stretches along the seawall past Greene St, William St, and Margaret St. to the K.W. Ferry Terminal.


View Two Complete Holiday Event Calendars Below

2018 Key West “Bight” before Christmas

Waterfront Schedule of Events

(2nd Islandwide Calendar Further Down)

Check back often for Updates!!

Wednesday, Nov. 21 – Kick off the Season!

Lighting of the Key West “Harbor Walk of Lights”

FREE – 6:00pm – Even more lights this year!

LOCATION: Gather on the Harbor Walk at Greene and Elizabeth St. to best see the official lighting of the … 2018 Key West “Harbor Walk of Lights”.

The main features will light up the night, including the Fishing Buoy Christmas Tree a real pine Nautical Christmas Tree and the Lobster Trap Christmas Tree all honoring the “Maritime History of Key West”.

Stroll the entire Harbor Walk of Lights for a merry infusion of holiday lights and nautical displays, including ship’s anchors, tropical birds, tropical fish, manatees and animated sea turtles.

With over 61,000 lights and 58 lighted palm trees, 2018 will be bigger than ever!

And on the Harbor Walk, theres always great Key West gift shopping, watersports gift certificates and all levels of dining and seasonal libations.

The Harbor Walk of Lights is lit every evening through New Year’s eve!

Saturday, Dec. 3

Schooner Wharf Tree Trimming Party

Saturday, Dec. 7

Pet Pictures with Santa TM

Hosted by The All Animal Clinic

FREE – 6:00 – 8:00pm

LOCATION: Look for Santa at the Nautical Christmas Tree at the foot of William St. on the Harbor Walk of Lights.

Credit: Key West The Newspaper

Saturday, Dec. 8

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. 15

Schooner Wharf Bar & Galley

28th 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, holiday music, dinner and drinks.


Saturday, Dec. 15

Sebago Lighted Boat Parade Party

7:30 – 9:30pm

Enjoy this annual holiday spectacle from a front row seat on the water.

Drinks and appetizers included!

Saturday, Dec. 15

Catamaran Echo Lighted Boat Parade Watch

7:30 – 9:30pm

Your private charter Champagne party for up to 14 guests! Free Santa Hats for everyone! Drinks and holiday appetizers included.

Sunday, Dec.16

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!

More Events Islandwide

2018 Key West Holiday Fest

Click here for more KWHF info and updates!

Dec. 7 – 14
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
Dec. 2
Old Stone Concert Series presents: Messiah 
7 p.m., at Key West United Methodist Church, 600 Eaton St. – FREE!

Old Stone Concert Series presents Christmas Community Chorus in the 35th annual performance.

Dec. 5 
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.

Dec. 6 – 23
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.

Dec. 6 – 23 
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.

Dec. 7 – 18
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.

Dec. 9 
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.

Dec. 13  
Sail with Santa on Fury Water Adventures

Festive trip to the reef including Holiday Music, Appetizers, Treats, Hot Chocolate, Beer, Wine, Champagne, Soda, Water & SANTA!!! Call 305-292-4600.

Dec. 14 – 16
“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.

Dec. 15 
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.

Dec. 19 
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.

Dec. 23
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.

Dec. 28 – 29
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.

Dec. 31
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, 2018 

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. for advertising or
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