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.


View Two Complete Holiday Event Calendars Below!


2021 Key West “Bight” before Christmas

Waterfront Schedule of Events

Enjoy the entire holiday season on the Key West waterfront!

(2nd Islandwide Calendar Further Down)

Please respect and practice healthy Covid precautions at ALL events!

Check back often for 2021 Updates!!

The 2021 Key West “Harbor Walk of Lights”TM

Celebrating the Maritime History of Key West

Wednesday, Nov. 24 – Free

Lighting of the “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. 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.

With thousands of lights in our Key West holiday palm trees, the 2021 holiday season at the Key West Historic Seaport is adding up to be spectacular!

HOLIDAY SHOPPING with dinner and drinks TOO!

The Key West Harbor Walk of Lights is lined with unique shops for:

  • amazing original artwork
  • tropical clothing and jewelry
  • unique souvenir gifts
  • and even gift certificates for watersports!

Enjoy great dining on the Harbor Walk of Lights, from casual to a culinary masterworks, along with holiday cocktails and live music at some of the most famous Key West watering holes.

The Harbor Walk of Lights comes alive every evening at dusk, past New Year’s eve! But is still fun and beautiful during the day. So don’t miss it!


November 15 – December 20

Key West Express Holiday Gift Sale!

Holiday Gifting the Whole Year Through

SAVE $60 on Key West Express Travel Voucher Gifts!
On Sale November 15th, 2021 – December 20th, 2021

Escape…Enjoy…Explore Key West with gifts that keep on giving for two whole years!
KW Express Travel vouchers are the perfect gift for any occasion.
Valid from January 1st, 2022 to December 31st 2023. 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 (from Key West Cakes!) and choice of holiday food included.

Friday, December 3 – FREE to attend

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

Professional photos by Rob O’Neal
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!

Photo Credit: Carol Tedesco

Saturday, December 4 – FREE

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 5 – FREE

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 engine, interior, original & custom, 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, December 5 – FREE to attend

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 11 – FREE

Schooner Wharf Bar & Galley and Absolute Vodka

30th Annual Key West Lighted Boat Parade

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.

Saturday, Dec. 11 – FREE to Attend

“Violins in Motion”

6:30pm – 8pm

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.

Saturday, Dec. 11

Schooner Appledore Lighted Boat Parade Party

7:30pm – 9:30pm

Be a participant in the 2021 The Lighted Parade aboard the Schooner Appledore II Parade Boat!
Trip Includes: Premium beer, boutique wines, wines and soft drinks. Very Limited Seating!

Friday, Dec. 25

Christmas Day Brunch Sail Aboard Schooner America 2.0

11:00am – 1:00pm
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!

Friday, 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!


2021 Key West Holiday Fest

Click here for more KWHF info and updates!

12/10/2021 & 12/17/2021 – 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.

Past stops on the Holiday Historic Inn Tour:

First Night:
  • Key West Butterfly Conservatory
  • The Gardens Hotel
  • Island City House
  • Amsterdam’s Curry Mansion

Second Night:

  • The Mermaid & The Alligator
  • Winslow’s Bungalows
  • Wicker Guest House
  • Weatherstation Inn

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

11/24/2021 thru 12/25/2021
MARC annual Christmas Tree Sale 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.

11/24/2021 – 5pm
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.

11/29/2021 – 6pm
Lighting of the Christmas Tree at Bayview Park

Annual Lighting of the Christmas Tree takes place at 6 pm at Bayview Park.

11/30/2021 – 5:30pm
Lighting of the Menorah Ceremony at Bayview Park

Annual Lighting of the Menorah Ceremony takes place at 5:30 pm at Bayview Park.

11/30/2021 – 7pm
The ReMARCable Tabletop Christmas Tree and Wreath Auction

Held at OPAL Key West Resort & Marina. Get your start on Holiday Cheer and support MARC by joining us at our annual Christmas Tree and Wreath Auction. Contact Becki Balcer 305-294-9526 ext. 25 or or visit us on Facebook @marckeywest.

12/01/2021 – 12/25/2021
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. Information and entry form available at

12/01/2021 – 6pm – 9:30pm
8th Annual POSH (Paws Often Steal Hearts) fundraising event for the Florida Keys SPCA

A formal evening at the Audubon House & Tropical Gardens with live music by The Yat Pack – a New Orleans-based band with an awesome horn and rhythm section that tips its hat to the days of Dean Martin, Frank Sinatra, Louie Prima, Bobby Darin and New Orleans jazz. The evening will conclude with a 2nd Line Parade from Audubon House to the Green Parrot Bar.

12/02/2021 – 9:30am – 2pm
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.


12/03/2021 – 5pm – 8pm

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.

December: 4, 11, 18, 19, 24 – 11am – 3pm
Visit With Santa at the Shops of Mallery Square

Visit with Santa at the Shops at Mallory Square  to add some magic to your holiday season. Visits with Santa begin on Saturday, December 4. Kids of all ages can visit Santa in the North Pole located upstairs in the historic Shops at Mallory Square  to share their holiday wishes and pictures with man in red. You decide your Santa Magic and can sit with Santa or have a socially distanced experience.  For the younger set, letter writing stations and a mail box will be on hand.

The Shops of Mallory Square – 291 Front St.

12/04/2021 – 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

12/10/2021 – 5pm – 9pm
Annual Holiday Concert & Bazaar at Custom House Museum

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

12/11/2021 – 10am – 2pm
Annual Parade of Paws & Holiday Bazaar at Higgs Beach / Higgs Dog Park

Benefits the Florida Keys SPCA. Costumes encouraged!

December: 12-17, 20-23, 26 – Departs 6:30pm & 8:30pm
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. All aboard for an hour tour that takes you to all the island’s most elaborately decorate houses, building and neighborhoods and caroling. Departs from Key West High School, 2100 Flagler Avenue.


December: 12-17, 20-23, 26 – Departs 6:30pm & 8pm
Old Town Trolley Holiday Lights & Sights Tours

No need to gas up the snowblower this year if you are planning a holiday escape to the Conch Republic! The Southernmost City is all a twinkle as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday – inspired competition. Multiple nightly tours convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city. Departs from Mallory Square.


12/14/2021 – 8pm
A John Waters Christmas at Key West Theater

John Waters live in person! Like an obsessed and shell- shock St. Nick from quarantine, John Waters, the “people’s pervert” or “queer Confucius” as the press recently called him hits the road again for his 25th Annual Xmas Tour. Bad little boys and girls and everybody in between and beyond, will be thrilled to take a sleigh-ride-of-sleaze down the slopes of good taste and over the ski jump of religious beliefs to a snow drift of candy cane anarchy.

12/18/2021 – 7am
Annual 5K Rudolph Red Nose Run

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. For information, online registration, or to download a snail-mail registration form, visit

12/19/2021 – 10am – 2pm
Key West Artisan Market: Holiday Shop Local

Key West Artisan Market invites you to “shop local” The show will be stocked with keys-made items perfect for gift giving this holiday season. The market is located at Indigenous Park. Free entry, free parking and BYOB ( Bring your own Bag)

12/24/2021 – 5pm-7pm
Holiday Jazz in the Gardens

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

12/24/2021 – 5pm-8pm
Noche Buena

Please join the Oldest House & Gardens for a traditional Key West Cuban Noche Buena 2021. Featuring roast pig, traditional Cuban sides, and sangria. The night of Christmas Eve is celebrated on December 24th every year for Latin American cultures. It is one of the biggest feast for the Christmas season and is the annual Spanish tradition. All proceeds benefit the Old Island Restoration Foundation.

12/25/2021 – 11am-1pm
Christmas Day Brunch on the Argo Navis Sail

Start a new Christmas tradition with friends and family on the only 75-foot luxury catamaran sailing yacht in Key West. Christmas Day brunch sourcing the best fare from the top Key West restaurants to bring you an amazing al fresco noshing experience. Endless mimosas, wine and craft beers, juices, and coffee. Don’t miss the Bloody Mary’s!

12/25/2021 – 12/26/2021 – 5pm-7pm
Holiday Jazz in the Gardens

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

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, 305-296-7701-7

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
KW “Bight” Before Christmas. for advertising or
to add a holiday event.


Photos by Rob O’Neal