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.

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View Two Complete Holiday Event Calendars Below!

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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!

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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 – 31 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.
Click below – SEE HOW TO ENTER YOUR BOAT!

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!

Stand by for 2021 Confirmation on the return of

“Violins in Motion”

Children’s Group Performance of Holiday Music!

Collecting donations for 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 little dose of Christmas spirit.

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!

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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!

ALWAYS GREAT SHOPPING, WATERSPORTS, DINING AND HOLIDAY LIBATIONS ON THE KEY WEST “HARBOR WALK OF LIGHTS”, THROUGH THE NEW YEAR!

For Events Below
Stand by for 2021 Updates!

2021 Key West Holiday Fest

Click here for more KWHF info and updates!

Stand by for 2021 Update!

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:
  • 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
Stand by for 2021 Update!
ANNUAL HOLIDAY ARTISAN MARKET

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

11/27/2021
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

Stand by for 2021 Update!
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

Stand by for 2021 Update!
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/

12/04/2021 thru 12/23/2021
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, 2021*
Phone 305-296-6688 | Web www.trolleytours.com

12/04/2021 thru 12/23/2021
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

Stand by for 2021 Update!
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

Stand by for 2021 Update!
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

Stand by for 2021 Update!
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

Stand by for 2021 Update!

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

Stand by for 2021 Update!
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/

Stand by for 2021 Update!
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

12/25/2021
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

12/25/2021
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

Stand by for 2021 Update!

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

12/31/2021

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

12/31/2021
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

12/31/2021
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.
info@dolphinecho.com for advertising or
to add a holiday event.

 

Photos by Rob O’Neal