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.

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View Two Complete Holiday Event Calendars Below!

2020 Key West “Bight” before Christmas

Waterfront Schedule of Events

(2nd Islandwide Calendar Further Down)

Check back often for 2020 Updates!!

While the 2020 Key West “Bight” before Christmas Holiday Celebration is subdued this year for Covid 19,
there are still plenty of reasons to visit the Key West and the Historic Seaport Harbor Walk at the holidays.
Please understand that all 2020 events are subject to cancellation / changes, but we will work to keep this website updated.
PLEASE wear your masks and social distance while enjoying the holidays in Key West.

Enjoy the entire holiday season on the Key West waterfront!

Starting Wednesday, Nov. 25 – lighting up as scheduled!

The 2020 Key West “Harbor Walk of Lights”TM

Celebrating the Maritime History of Key West

Easily stroll the Harbor Walk socially distanced and “don your festive Holiday Mask” for healthy holiday fun! See thousands of lights and sparkling holiday displays – on the water!

While there is no grand gathering for the official lighting ceremony this year, this six-week event will last throughout the entire holiday season!

LOCATION: The Key West Historic Seaport, on the “Harbor Walk” running from Elizabeth St. past William St., Margaret St. all the way to Grinnell St. and the Key West Ferry Terminal.

Always FREE: lighting up every evening from dusk to dawn, starting on November 25 (Thanksgiving eve) through the New Year.

The Key West “Harbor Walk of Lights” traditional main features will light up every 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.

Also with thousands of lights in lighted palm trees, the Key West Historic Seaport is the safe place to feel the magic of Christmas in 2020!

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. 6

Schooner Wharf Bar and Galley – Tree Trimming Party

Schooner Wharf Bar will share warm season’s greetings and plenty of holiday “spirits” at its annual Tree Trimming Party and toy drive beginning at 6 p.m. on Sunday, Dec. 6th. Please stay healthy, masks required while not seated.

Maritime merry makers will deck the halls and make dreams come true at the popular waterfront winter wonderland. Ornaments will be entered in a contest and prizes will be awarded for the Most Original, Most Nautical and 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 gifts for holiday gift giving.

Twenty one years ago the Schooner Wharf Breakfast Club initiated a Toy Drive on Tree Trimming Day, benefiting Toys for Tots, Angels–Just 4 Kids and Key West Cares. Each of Santa’s helpers who donates an unwrapped gift to one (or all!) of these worthwhile causes 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.

Come make our tree yours! Happy Holidays from the crew of Schooner Wharf Bar and Galley!

Sunday, Dec. 20, 2020

The Conch Republic Seafood 2020 “Holiday Classic Car show”
FREE • 11:00am – 3:00pm

For Holiday health and safety – Social distancing maintained throughout the event, cars spaced 6′ apart, Masks required – “don your festive Holiday Mask” for healthy holiday fun!

LOCATION: Conch Republic Seafood Company parking lot – Greene & Elizabeth St.

Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter.
See classic cars from every era decked out for the holidays!
Great food and drinks available all day!

VOTE for the “Peoples Choice” award and the “Most creative Holiday Mask”.

Awards also for: BEST engine, BEST interior, BEST original, BEST custom, Best in Show!

Official show of the “Florida Keys Southernmost Car Club”

Non-member cars may enter same day FREE with an unwrapped toy!

Friday, Dec. 25, 2020

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, crudités, and other delicious Christmas day treats!

Postponed until 2021

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

The All Animal Clinic “Pet Pictures with Santa” event is cancelled for 2020 because of health concerns and the nature of the event – but come get in the sprit on the Harbor Walk of Lights anyway!

HOLIDAY PHOTO LOCATION: At the “Nautical Christmas tree” at the foot of William St. on the “Harbor Walk of Lights” and get a great Holiday selfie! Because the 2020 “Pet Pictures with Santa” event was to raise money for the Boys & Girls Club of Key West, please continue to support them, especially in 2020, by donating at https://bgckeywest.org. See below for last year’s Pet Pictures.

See you in 2021!

DONATE

Photo Credit: Carol Tedesco

Postponed until 2021

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!

Postponed until 2021 – watch for 2020 updates!

Schooner Wharf Bar & Galley

30th 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!

Postponed until 2021 – still sailing daily in 2020!

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!

Postponed until 2021- still sailing daily in 2020!

2020 public trips less than half full for health and safety – Private charters for 2 – 19 passengers!

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. 

Postponed until 2021

“Violins in Motion”

Children’s Group Performance of Holiday Music!

Collecting donations for JDRF and Juvenile Diabetes Research

FREE 6:30pm – 8:00pm

<pLOCATION: 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!

More Events Islandwide

2020 Key West Holiday Fest

Click here for more KWHF info and updates!

Postponed until 2021 – but enjoy a self guided light tour this year!

Key West Holiday Historic Inn Tour

(There is no organized tour in 2020, but still lights to enjoy on your own 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.

2019 tour stops – still a sight to see in 2020:

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
11/27/2020 thru 12/24/2020
ANNUAL HOLIDAY ARTISAN MARKET

All Day
Online market – local artists! View at https://tskw.org/

11/27/2020
MARC annual Christmas Tree Sale Lot

(1401 Seminary Street) opens 11/27. Hours 9AM-7:45PM Daily until 12/24 or trees are sold out. Poinsettias—wreaths—garland—holiday accessories—ornaments AND great local gifts! New Shipments arrive 12/1 and 12/8! Contact Becki Balcer 305.294.9526 ext. 25 or becki.balcer@gmail.com or visit us on Facebook @marckeywest

12/01/2020
Key West Garden Club Holiday Lighting Party

9:30am to 2pm at Fort West Martello Tower at Higgs Beach, 1100 Atlantic Ave, 305-294-3210.

The Key West Garden Club is decorating historic Fort East Martello for the holidays, and much of it will be visible at night when walking or driving by. Admission to the Fort grounds is free; donations cheerfully accepted. Masking and social distancing required. keywestgardenclub@gmail.com or Keywestgardenclub.com

12/03/2020
Key West Holiday Movie Challenge Launch

Christmas Community Chorus in the 35th annual performance.

Online Filmmaking Competition + Screening, The Studios of Key West – Thursday, December 3 at 7pm EST – Virtual

Virtual Screening: Saturday, December 19 thru Dec 26 What would Love Actually sound like with a Conch accent? What if It’s a Wonderful Life’s George Bailey grew up in Key West instead of Bedford Falls? Participants have one long weekend to reimagine their favorite Christmas movies with a Key West twist. The challenge is open to filmmakers of all levels—even first timers. All entries are eligible for random door prizes, and People’s Choice awards will be given in two categories: short film and mini challenge https://tskw.org/key-west-holiday-movie-challenge/

12/04/2020 thru 12/23/2020
Old Town Trolley Holiday Lights & Sights Tours

No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Lights & Sights Tour! 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.6:30pm & 7:15pm, No tours offered December 5, 2020*
Phone 305-296-6688 | Web www.trolleytours.com

12/04/2020 thru 12/23/2020
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 Tour Train for their annual holiday lights tour of the island. All aboard for an hour tour that takes you to all of the island’s most elaborately decorated houses, buildings and neighborhoods and caroling. 6:30pm and 7:15pm., *No tours available December 5, 12 or 17. Subject to change. Departs from: Key West High School, 2100 Flagler Avenue. Phone 305-294-5161

12/06/2020
MARC House Holiday Open House

11AM-2PM at 1401 Seminary Street, featuring new art by June Klausing and our ReMARCable Clients. Light refreshments, Holiday music, and great gift ideas! Contact Becki Balcer 305.294.9526 ext. 25 or becki.balcer@gmail.com or visit us on Facebook @marckeywest

12/09/2020
The ReMARCable Tabletop Christmas Tree and Wreath Auction

7pm to 9pm at Margaritaville Resort LIMITED SOCIALLY DISTANCING SEATING AVAILABLE. Also, there will be a private zoom room for the auction. Contact Becki Balcer 305.294.9526 ext. 25 or becki.balcer@gmail.com or visit us on Facebook @marckeywest

12/13/2020
Key West Artisan Market: Fill the Pantry SOS Edition

Higgs Beach, Indigenous Park @ 10am to 3pm The focus is on fresh, locally sourced food offered by our growers and makers. Share the bounty with the SOS Foundation by bringing canned goods and donations to help the SOS Callahan Community Kitchen fill their pantries to provide meals and snacks for our community’s underserved children. Free entry, free parking. Please BYOB (bring your own bags). Contact: Sean Krikorian, T: 305-294-7994, E: Sean@DailyPlan-it.net Web: https://www.facebook.com/KeyWestArtisanMarket

12/13/2020 and 12/14/2020

Holiday Gift Show – Collections Key West Gallery

6810 Front Street, Stock Island 11-4:00, also by appt., Tel: 305-923-4778 E-mail: karen@collectionskw.com Web: collectionskw.com

12/19/2020 thru 12/26/2020
Key West Holiday Movie Challenge Virtual Screening

Christmas Community Chorus in the 35th annual performance.

Online Filmmaking Competition + Screening, The Studios of Key West What would Love Actually sound like with a Conch accent? What if It’s a Wonderful Life’s George Bailey grew up in Key West instead of Bedford Falls? Participants have one long weekend to reimagine their favorite Christmas movies with a Key West twist. The challenge is open to filmmakers of all levels—even first timers. All entries are eligible for random door prizes, and People’s Choice awards will be given in two categories: short film and mini challenge. https://tskw.org/key-west-holiday-movie-challenge/

12/20/2020
Key West Artisan Market “Shop Local for the Holidays”

Higgs Beach, Indigenous Park from 10am to 3pm The show will be stocked with keys-made items perfect for gift giving this holiday season. Free entry, free parking. Please BYOB (bring your own bags). Contact: Sean Krikorian, T: 305-294-7994, E: Sean@DailyPlan-it.net Web: https://www.facebook.com/KeyWestArtisanMarket

12/25/2020
Christmas Dinner at Matt’s Stock Island Kitchen & Bar

4-10pm 7001 Shrimp Road, Key West FL 33040 – Contact info: Jenny Lorenz, E-mail: jlorenz@perrykeywest.com, Tel: 305-296-1717, Web: mattsstockisland.com

12/25/2019
Christmas Ultimate Adventure

Trip Time: 10:00am – 4:00pm, Check-In: 9:00am, Departs from 631 Greene Street. Activities: Reef Snorkel, Parasail, Jet Ski, Banana Boat Ride & Water Park Sodas, Water, Beer & Wine Included (Alcohol served after activities are completed) Breakfast & Lunch Included – Featuring a Special Holiday Themed Menu!
Phone # 305-292-4600 | https://www.furycat.com/key-west/christmas

12/27/2020

Higgs Beach, Indigenous Park from 10 am to 3 pm. The artists will be stocked with keys-made items perfect to treat yourself to the gift you… Contact: Sean Krikorian, T: 305-294-7994, E: Sean@DailyPlan-it.net Web: https://www.facebook.com/KeyWestArtisanMarket

12/31/2019

New Year’s Eve Sunset Sails

Champagne Sunset Cruise

Trip Time: 5:15pm – 6:45pm, Check-In: 4:45pm, Departs from 631 Greene Street
Phone # 305-292-4600 | https://www.furycat.com/key-west/new-years-eve

Glass Bottom Boat Reef Eco Tour + Sunset Cruise

Trip Time: 4:00 – 6:00pm, Check-In: 4:30pm, Departs from 0 Duval street
Phone # 305-292-4600 | https://www.furycat.com/key-west/new-years-eve

Commotion on the Ocean Live Music Sunset Sail

Trip Time: 5:00pm – 7:00pm, Check-In: 4:30pm, Departs from 631 Greene Street
Phone # 305-292-4600 | https://www.furycat.com/key-west/new-years-eve

12/31/2020
New Year’s Eve Dinner at Matt’s Stock Island Kitchen & Bar

4-10pm 7001 Shrimp Road, Key West FL 33040 – Contact info: Jenny Lorenz, E-mail: jlorenz@perrykeywest.com, Tel: 305-296-1717, Web: mattsstockisland.com

12/31/2020
Key West New Year’s Eve Celebrations – To be announced – please watch for 2020 updates!
  • 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.
info@dolphinecho.com for advertising or
to add a holiday event.

 

Photos by Rob O’Neal