Key West “Bight” before Christmas Celebration

Scroll down for two Holiday Calendars

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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!

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”™

Music at 5:00pm
Lighting at 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!

Sunday, Dec. 1

Schooner Wharf Bar and Galley – Tree Trimming Party

Friday, Dec. 6

Pet Pictures with Santa™ – Hosted by The All Animal Clinic

FREE to attend. 6:00pm – 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!

Photo Credit: Carol Tedesco

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 Appledore Lighted Boat Parade Party

7:30pm – 9:30pm

Be a participant in the 2019 The Lighted Parade aboard the Schooner Appledore II Parade Boat!

Trip Includes: Premium beer, boutique wines, wines and soft drinks. Very Limited Seating!

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. 


Saturday, Dec. 14

Sebago Lighted Boat Parade Party

7:30pm – 9:30pm

Enjoy this annual holiday spectacle from a front row seat on the water.
Drinks and appetizers included!

Saturday, Dec. 14

Catamaran Echo Lighted Boat Parade Watch

7:30pm – 9:30pm

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

Sunday, Dec.15

Conch Republic Seafood
“Holiday Classic Car Show”

FREE • 11:00am – 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 6:30pm – 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.

Wednesday, Dec. 25

Christmas Day Brunch Sail Aboard Schooner America 2.0

Enjoy Christmas morning the Key West way – sailing!

11:00am – 1:00pm

This two-hour Christmas Day Brunch Sail features complimentary mimosas, Bloody Marys, wine, beer, soft drinks, and water.

Brunch is provided, including spiraled ham, bagels and pastries, meats and cheeses, smoked salmon, crudite, and other delicious Christmas day treats!


More Events Islandwide

2019 Key West Holiday Fest

Click here for more KWHF info and updates!

Friday, December 6
Friday, December 13

Key West Holiday Historic Inn Tour

6pm – 8pm • 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:
  • Hemingway Rum Co. Distillery
  • Amsterdam’s Curry Mansion Inn
  • The Weatherstation Inn
  • The Gardens Hotel
  • Island City House Hotel

Second Night:

  • Avalon Bed & Breakfast
  • Wicker Guesthouse
  • The Mermaid & The Alligator
  • Santa Maria Suites Resort
  • Key West Butterfly & Nature Conservatory
Sunday, December 1
Old Stone Concert Series

Christmas Community Chorus in the 35th annual performance.

Wednesday, December 4
Wesley House Family Services Key West Lighted Bike Ride

7pm. (Registration/Check-in: 6pm)

It’s a festive, costumed peddling party toy drive which launches from Bayview Park. Registration is one unwrapped new toy.

Monday, December 9 through Sunday, December 22
Conch Tour Train Holiday Lights Tours

Multiple nightly tours begin with cider and cookies, and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

Friday, December 6 through Monday, December 23
Old Town Trolley Holiday Lights & Sights Tours

Multiple nightly tours convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

Thursday, December 12
7th Annual POSH – Paws Often Steal Hearts

6pm – 9pm

Benefiting Florida Keys SPCA! Benefit is located at the Audubon House & Tropical Garden. There will be live music, silent auction, Tapas-style appetizers, complementary specialty welcome drink and local priced cash bar! Tickets in advance $40 and $45 at the door, available at FKSPCA POSH Tickets.

Saturday, December 14
Annual Parade of Paws & Holiday Bazaar

Higgs Beach / Higgs Dog Park
10am – 2pm (9:00am check-in)

Benefits the Florida Keys SPCA. Costumes encouraged!

*Sunday, December 15
Christmas on the Sheriff’s Animal Farm

FREE 1pm – 3pm

The farm is open to the public from 1 to 3pm. Come visit the animals and have a photo with Santa. It’s free and donations are appreciated.

*Due to the holidays, please note that the farm is only open for ONE Sunday during the month of December.

Wednesday, December 18
Artisan Market, Key West

FREE 10am – 2pm

A “shop local” holiday tradition, the open-air bazaar, this year at Higgs Beach, 100 Atlantic Blvd., is filled with Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages.

Wednesday, December 18
4th Annual Custom House Holiday Concert & Bazaar
Custom House Museum

FREE 5pm – 9pm

This festive free party features Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show.

Photo Credit: Carol Tedesco

Sunday, December 22


Lighting of the Menorah at Bayview Park.
Sunday, December 22
Holiday Jazz in the Gardens

FREE 5:30pm – 7:30pm

Festive outdoor jazz performance at the Gardens Hotel. Cash bar & large wine selection.

Wednesday, December 25
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!!!

Friday, December 27 – Saturday, December 28
60th Annual Key West House and Garden Tour

3pm – 6pm

Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3pm-6 pm 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.

Tuesday, December 31
Annual Key West Dachshund Walk

12:00 noon

Dachshund’s and Dachshund impersonators along with their human companions gather at Fleming and Whitehead Streets before parading through downtown streets lined with adoring fans.

Tuesday, December 31
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, 305-296-7701-7701

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
to add a holiday event.


Photos by Rob O’Neal