Key West “Bight” before Christmas® Celebration

At the Key West Bight Marina

Scroll down for two Holiday Calendars

Watch Video!

Find tropical Holiday Fun on the Key West waterfront – all December!

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.

Photos by Carol Tedesco & Rob O’Neal


View Two Complete Holiday Event Calendars Below!

On the Historic Seaport Harbor Walk – Click for Info!
Click to Dive!

2022 Key West “Bight” before Christmas®

Waterfront Schedule of Events

Enjoy the entire holiday season on the Key West waterfront!

(2nd Islandwide Calendar Further Down)

Check back often for 2022 Updates!!

The 2022 Key West “Harbor Walk of Lights”TM

Celebrating the Maritime History of Key West

Wednesday, Nov. 23 – Free

The Lighting of the 2022 “Harbor Walk of Lights”

Lights come on at 6:00pm, holiday music starts at 5:00pm

LOCATION: The Harbor Walk plaza at Greene and Elizabeth St. for the best view. Enjoy creative holiday displays and thousands of lights honoring the “Maritime History of Key West”.

The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree.

Walk along the water’s edge for a merry infusion of colorful lights and nautical holiday displays. See light sculptures of ship’s anchors, tropical birds, tropical fish, a flock of pink flamingos, jolly pelicans, merry manatees, animated sea turtles and dancing dolphins, and even a festive moray eel, all under brightly lit holiday palm trees!

And with over 30,000 ADDITIONAL lights this year around the Historic Seaport, the 2022 Key West “Harbor Walk of Lights” is promised to be a real holiday treat!

Photos by Carol Tedesco & Rob O’Neal

November 1 – December 20

Key West Express 2022 Holiday Sale!

Holiday Gifting the Whole Year Through

SAVE $66 on Key West Express Travel Vouchers!
On Sale November 1st, 2022 – December 20th, 2022

Escape…Enjoy…Explore Key West with a gift that keeps on giving for two whole years!
KW Express Travel vouchers are the perfect gift for any occasion.
Valid for travel from January 1st, 2023 to December 31st 2024.

LIMITED TIME SALE – No blackout dates!

Happy Holidays from Key West Express!

December 1 – January 15, Book Now!

Private Holiday Champagne Party on Catamaran Echo

Private 2 hour Sail – Morning, Afternoon or Sunset Holiday cruise!
All ages welcome.
Your private charter Holiday party for up to 14 guests!
Premium drinks, mimosas, awesome Christmas cookies and choice of holiday food included.

Photo Credit: Carol Tedesco

Saturday, December 3 – FREE

2022 Key West City “Hometown Holiday Parade”

Starts at 7:00pm

LOCATION: Parade starts on Truman Ave. (at White St.) then proceeds 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!

Sunday, December 4 – FREE to Attend
6:00pm – 8:00pm

2022 Pet Pictures with Santa™ – Hosted by The All Animal Clinic

Professional photos by Mary Martin
LOCATION: At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St.

Santa pics with pets and kids big and small, treats for all! Pictures with Santa are $20 (cash only) to benefit our local Boys & Girls Club.

Get professional furry family photos for that special holiday card this year, and also support the Kids in the lower Keys!

Sunday, December 4 – FREE to Attend

Schooner Wharf Bar 2022 Tree Trimming Party and Toy Drive

Starting at 6:00PM

LOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St.

Maritime merry makers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Great PRIZES for the Best Handmade Ornaments that are:

  • Most Original
  • Most Nautical
  • Most Popular with the holiday crowd

All tree trimmers will be treated to a free holiday cocktail — egg nog, hot apple jack or Swedish Glogg.

Then step into Santa’s southernmost workshop at Schooner Wharf. Share the holiday spirit, as local artists and authors sign and sell ORIGINAL WORKS for HOLIDAY GIFT GIVING.

TOY DRIVE for Toys for Tots, Angels–Just 4 Kids, Key West Cares.

Each of Santa’s helpers who donates an unwrapped gift will also receive a free holiday drink from Schooner Wharf Bar.

Some of our favorite local musicians will be playing Holiday Tunes, Reggae, and Calypso with the island sound of Steel Drums to round out the festivities.

Saturday, December 10 – FREE

Schooner Wharf Bar & Galley and Absolute Vodka

31th Annual Key West Lighted Boat Parade 2022

Music at 6:00, 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 live holiday music performances, dinner and drinks.
Photos courtesy of Carol Tedesco

Saturday, Dec. 10

Schooner Appledore Lighted Boat Parade Party

7:30pm – 9:30pm

Be a participant in the 2022 The Lighted Parade aboard the Schooner Appledore II Parade Boat!
Trip Includes: Premium beer, boutique wines, wines and soft drinks. Very Limited Seating!

CANCELLED for 2022 – Back in 2023!

“Violins in Motion”

Children’s Group Performance of Holiday Music!
Collecting donations for Make A Wish Foundation

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 little dose of Christmas spirit.

Sunday, December 18 – FREE

2022 Conch Republic Seafood “Holiday Classic Car Show”
FREE • 11:00am – 3:00pm

LOCATION: Conch Republic Seafood Company – on the Harbor Walk of Lights at Greene St.

TOY DRIVE: Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter.

VOTE for the “Peoples Choice” award for: BEST sports car, pick up, engine, interior, original & custom, pre & post 1950, Best in Show.

See classic cars from every era decked out for the holidays!
Run by the Florida Keys Southernmost Car Club.
Non-member cars may enter same day FREE with an unwrapped toy!

Sunday, Dec. 25

Christmas Day Brunch Sail Aboard Schooner America 2.0

10:00am – 12:00pm
Enjoy Christmas morning the Key West way – sailing!

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, crudités, and other delicious Christmas day treats!

Saturday, December 31

New Year’s Eve Celebrations All around the Harbor Walk of Lights! Many choices for Dinner, Drinks, and a party on the Waterfront!


Lowering of the Pirate Wench at Midnight!

LOCATION: Schooner Wharf Bar and Galley On the Harbor Walk of Lights at William St.

Great Food, Holiday Drinks and LIVE Music!

Party starts early in the day with 3 Local and National Acts. Party Favors – Champagne & Fun

The Unique Schooner Wharf Bar’s Seaport Tradition!


2022 Key West Holiday Fest

Click here for more KWHF info and updates!

12/09/2022, 12/16/2022 – 6pm-8pm
Key West Holiday Historic Inn Tour

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.

2022 stops on the Holiday Historic Inn Tour:

December 9th:
  • Key West Butterfly & Nature Conservatory* (1316 Duval St.)
  • The Mermaid & The Alligator
  • Winslow’s Bungalows
  • Weatherstation Inn

December 16th:

  • Hemingway’s Library at Papa’s Pilar Distillery * (201 Simonton St.)
  • The Marquesa Hotel
  • The Gardens Hotel
  • Island City House Hotel

Tickets can be purchased by calling 305-296-4959 or on any day prior to the date of the tour.

11/23/2022 thru 12/24/2022
MARC annual Christmas Tree Sale Lot

Fresh pines and wreaths for sale. 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.

11/27/2022 6PM - 8PM
Messiah Concert at Key West Methodist

Join us for the Messiah concert at Key West Methodist church
More info at:

11/28/2022 6PM - 8PM
Lighting of the City of Key West Christmas Tree

Annual Lighting of the City Christmas Tree takes place at Bayview Park.9th Annual POSH (Paws Often Steal Hearts) fundraising event for the Florida Keys SPCA.

12/1/2022 6PM - 9PM
9th Annual POSH (Paws Often Steal Hearts) fundraising event for the Florida Keys SPCA

Sunset Social Drinking Club’s formal to raise money for the FKSPCA.
This year’s entertainment is SUENALO! Audubon House 205 Whitehead Street
More info and tickets at:

12/2/2022 4PM - 8PM

Wesley House Family Services BeLighted Bike Ride and Holiday Village at Coffee Butler Amphitheater

More info and tickets at:

12/03/2022 – 7pm
Key West Hometown Holiday Parade

Hundreds of 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.

Begins at Truman Ave & White St

12/07/2022 – 12/11/2022

Nutcracker Key West

The largest community production brought to the stage in Key West. This year, 60 of our community’s children and adults and 15 professional dancers from around the world will join together again for to produce this outstanding historical recreation of Key West’s version of the Nutcracker, Nutcracker Key West.

More info and tickets at:

2022 December 8, 11-13, 16-23
Conch Tour Train Holiday Lights Tours

It won’t get cold, and it will not snow, but the festive lights have the city aglow. Join the Conch Train for their annual holiday lights tour of the island.


2022 December 8 – 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. Departs from Mallory Square.


12/9/2022 5PM - 9PM
6th Annual Holiday Concert & Bazaar at Custom House Museum

This festive free party features Key West’s finest artisans, musicians and choirs, food and libations, and a holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House.

More info at:

12/10 and 12/16/2022 12PM - 2PM
Visit Santa at the (Southernmost) North Pole:

Mallory Square

12/10/2022 10AM - 2PM
9th Annual Parade of Paws

Our 9th annual Parade of Paws is here! Join us on Saturday December 10th at Higgs Dog Park to celebrate all the dogs in our community!

More info at:

12/17/2022 7AM
14th Annual 5K Rudolph Red Nose Run

Don your festive holiday jammies and join in the 14th annual Positive Step 5K Rudolph Red Nose Run: Southernmost Beach Cafe.

More info at:

12/18/2022 5AM - 6PM
Lighting of the City of Key West Menorah Ceremony

Annual Lighting of the City Menorah Ceremony takes place at Bayview Park.

12/25/2022 5AM - 7PM
Holiday Jazz in the Gardens

Free. Join us at the Gardens Hotel for a festive outdoor jazz performance. Cash Bar.

More info at:

Key West New Year’s Eve Celebrations

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!

Support the
Key West “Bight” Before Christmas®. for advertising or
to add a holiday event.


Photos by Rob O’Neal