19th Annual
Key West “Bight” before Christmas® Celebration
At the Key West Bight Marina
Scroll down for two Holiday Calendars
Watch Video!
19th Annual
Find tropical Holiday Fun on the Key West waterfront – all December!
The 19th Annual 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.
And this year’s display is sending Lots of Love from the heart of Key West to Jimmy Buffett!
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
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View Two Complete Holiday Event Calendars Below!
2024 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 2024 Updates!!
The 2024 Key West “Harbor Walk of Lights”TM
Celebrating the Maritime History of Key West
Wednesday, Nov. 27 – Free
The Lighting of the 2024 “Harbor Walk of Lights”
at the Key West Historic Seaport
Main Harbor Walk Lighting at the 2024 “Fishing Buoy Christmas Tree”
Lights come on at 6:00pm – holiday music starts at 5:00pm – Greene and Elizabeth St. plaza.
Santa and Mrs Clause will be making a NICE list and passing out treats!
SECOND lighting of the 2024 “Lobster Trap Christmas Tree”
Lights come on at 7:00pm, holiday music starts at 6:00pm – Margaret St. plaza (Old Lands End Village).
There will be holiday cookies and candy canes for the children!
Enjoy creative holiday displays and thousands of lights honoring the “Maritime History of Key West”.
With 3 blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport, the 2024 Key West “Harbor Walk of Lights” is destined to bring miles of holiday smiles to our One Human Family of visitors and locals alike.
Harbor Walk of Lights is on every night from Thanksgiving eve through New Year’s eve!
Please join us at the “Lighting of the Harbor Walk” to kickoff the “Cheryl Cates Toy Drive”.
Bring a toy, or toys will be available at the “Imagination Station” table to purchase and donate.
ALSO, be there for a special announcement from the Cheryl Cates Toy Drive.
Photos by Carol Tedesco & Rob O’Neal
Sunday, December 1 – FREE to Attend
Schooner Wharf Bar 2024 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.
Bring a donation for the “Cheryl Cates Memorial Toy Drive” by Angles Just 4 Kids!
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.
Thursday, December 5 – FREE to Attend
6:00pm – 8:00pm
2024 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 $25 (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!
Saturday, December 7 – FREE
2024 Key West City “Hometown Holiday Parade”
Starts at 6:30pm
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!
Saturday, December 14 – FREE
Schooner Wharf Bar & Galley and Absolute Vodka
33rd Annual Key West Lighted Boat Parade 2024
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 and to see the decked out holiday boats still in dock.
Click below – SEE HOW TO ENTER YOUR BOAT!
Come early for live holiday music performances, dinner and drinks and to see the decked out holiday boats still in dock.
Click below – SEE HOW TO ENTER YOUR BOAT!
Photos courtesy of Carol Tedesco
CHECK BACK for 2024 date!
“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.
Starting Friday, November 29 – Through the Holidays, Book Now!
Private Holiday Party Charter on Catamaran Echo
Private 2 hour Sail – Morning or Afternoon or Sunset!
All ages welcome.
Your private Holiday Party Charter for up to 12 guests on Echo 2 and 20 Guests on Echo 3!
Premium drinks, mimosas, Christmas cookies and choice of holiday food included.
Sunday, December 15
The Florida Keys Southernmost Car Club presents
2024 “Holiday Classic Car Show” & Toy Drive
FREE • 11:00am – 3:00pm
LOCATION: Conch Republic Seafood Company parking lot – 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, honoring founder Dick Moody.
Non-member cars may enter same day FREE with an unwrapped toy!
Wednesday, Dec. 18 – Tuesday, Dec. 24
Cocoa and Carols: Live Holiday Music Cruise Aboard Schooner America 2.0
7:00pm – 8:30pm
A festive Christmas cruise featuring holiday live music and cheer!
Please join us for this special Key West holiday cruise tailored for friends, family, and all your loved ones during the Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 in full holiday decor for a 1.5-hour cruise in Key West harbor while we listen to some of our favorite Christmas hits played live from our decks! Delicious hot cocoa, cookies, and treats for all our guests are included!
Wednesday, Dec. 25
Christmas Day Brunch Aboard Schooner America 2.0
10:00am – 12:30pm
Enjoy Christmas morning the Key West way – sailing!
This 2.5 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!
Sunday, 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!
ALWAYS GREAT SHOPPING, WATERSPORTS, DINING AND HOLIDAY LIBATIONS ON THE KEY WEST “HARBOR WALK OF LIGHTS”, THROUGH THE NEW YEAR!
2024 Key West Holiday Fest
PLEASE CHECK BACK FOR 2024 UPDATES!
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.
Stops on the 2024 Holiday Historic Inn Tour:
- Night #1 – Friday, Dec 6 from 6:00 – 8:00pm
- Hemingway’s Social Club at Papa’s Pilar Distillery
- Lighthouse Hotel
- Wicker Guesthouse
- Gardens Hotel
- Night #2 – Friday, Dec 13 from 6:00 – 8:00pm
- Key West Butterfly Conservatory
- The Mansion on the Sea
- Island City House
- The Mermaid & The Alligator
Tickets can be purchased by calling 305-296-4959 or online https://keystix.com/calendar
Nov. 29 – Dec. 24, 2024
MARC annual Christmas Tree Sale Lot
Fresh pines and wreaths for sale. More than 1500 trees travel from up North 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.
Nov. 29, 2024 | 10:00 – 6:00pm
Black Friday Holiday Shopping Extravaganza
At the Truman Waterfront by the USCGC Ingham Maritime Museum.
Fine arts and crafts, jewelry, apparel, produce, delicious foods and more abound at this open-air bazaar.
Nov. 29 & 30 | Dec. 5 & 6, 2024
FIESTA DE NAVIDAD
At the San Carlos Institute – 516 Duval St.
Fiesta de Navidad delivers a festive extravaganza to ignite the holiday spirit. With world-class Latin dance and vibrant costumes,
this joyful celebration also offers the opportunity for audience members of all ages to dance on stage with a live band!
More info and tickets at: https://kwinternationaldancecompany.com/fiesta-de-navidad.
Dec. 1, 2024 | 6:00pm
Schooner Wharf Bar 2024 Tree Trimming Party and Toy Drive
On the Harbor Walk of Lights at William St.
Donate an unwrapped gift for Cheryl Cates Memorial Top Drive – receive a free holiday drink!
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.
Click https://schoonerwharf.com/special.htm#current for more info!
Dec. 1, 2024 | 7:00 pm
Messiah Concert at Key West Methodist
Join us for the Messiah concert at Key West Methodist church
More info at: https://keywestumchurch.org/
Dec. 2, 2024 | 6:00 pm
Lighting of the City of Key West Christmas Tree
Annual Lighting of the City Christmas Tree takes place at Bayview Park.
Dec. 3, 2024 | 5:30 pm
The ReMARCable Decorated Table Top Tree & Wreath Auction
At Opal Key Resort, 245 Front St., presented by First Horizon Foundation.
Preview at 5:30pm; auction at 7:00pm.
Dec. 5, 2024 | 6:00 pm – stop by for a “Pet Picture with Santa” FIRST
The 11th Annual FKSPCA Fundraiser, POSH (Paws Often Steal Hearts)
The Audubon House & Gardens!
11th Annual POSH Gala, a fundraising event for the Florida Keys SPCA
Enjoy this gala style affair encouraging guests to dress up and don their favorite fascinators.
More info and tickets at: https://fkspca.org/event/posh-paws-often-steal-hearts/
Dec. 5, 2024 | 6:00 – 8:00pm
Pet Pictures with Santa™
Raising money for our local Boys & Girls Club!
Professional photos by Rob O’Neal
LOCATION: Key West Historic Seaport
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!
Dec. 5 – 15, 2024
Nutcracker Key West
Tennessee Williams Theatre
Sugarplum fairies trade tutus for sea fans, and the battle between the mice and the soldiers takes on a whole new flavor. This whimsical production is a sumptuous blend of art, music, and local flair, perfect for the entire family. Our community’s talented children and adults along with professional dancers from around the world will join together again to produce this semi-annual historical recreation of Key West’s version of the Nutcracker – Nutcracker Key West.
More info and tickets at: https://nutcrackerkeywest.com
Dec. 6, 2024
Holiday Village & BeLighted Bike Ride
By Wesley House Family Services
At Coffee Butler Amphitheater
Holiday Village 4:00pm – 8:00pm
BeLighted Bike Ride starts 8:00pm
More info and tickets at:
Dec. 7, 2024 | starts at 6:30 pm
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
Dec. 8, 2024 | 1:00 – 3:00pm
Christmas on the Farm
The Monroe County Sheriff’s Office invites everyone to come meet the animals during its annual Christmas on the Farm event.
5501 College Road, Stock Island. Donations welcomed!
Dec. 9-10 & 13-23, 2024
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.
More info at: https://www.conchtourtrain.com/key-west-christmas-holiday-tours/
Dec. 9 – 23, 2024
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.
More info at: http://www.trolleytours.com/
Dec. 13 – 30, 2024
Key West Waterfront Winter Wonderland
The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more. Closed Christmas Eve and Christmas Day.
More info at: https://www.thekeywestamp.com/events/detail/waterfront-winter-wonderland
Dec. 13, 2024 } 5:00 – 9:00 pm
Annual Holiday Concert & Bazaar
Key West Museum of Art & History – Custom House 281 Front Street
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: https://www.kwahs.org/bazaar/
Dec. 14, 2024 | 7:00am
16th Annual 5K Rudolph Red Nose Run
Don your festive holiday jammies and join A Positive Step of Monroe County’s 5K Rudolph Red Nose Run – the PJ Edition. Registrants receive a free t-shirt.
Runners and walkers of all ages and abilities are welcome to participate.
More info at: https://www.apsmc.org/annual-5k
Dec. 15, 2024 | 11:00am – 3:00pm
The Florida Keys Southernmost Car Club
2024 “Holiday Classic Car Show” & Toy Drive
At Conch Republic Seafood Company parking lot – Historic Seaport Harbor Walk of Lights at Greene St.
Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter – FREE non-member car entry.
VOTE for the “Peoples Choice” award for: BEST sports car, pick up, engine, interior, original & custom, pre & post 1950, Best in Show.
Run by the Florida Keys Southernmost Car Club, honoring founder Dick Moody.
See classic cars from every era decked out for the holidays!
Dec. 15 and 22, 2024
Christmas Cantata
11AM at Fifth Street Baptist Church
You are invited to Fifth Street Baptist Church for their annual Christmas cantata.
The choir will sing a collection of contemporary music as well as familiar Christmas carols to celebrate the season.
Come join this event with the whole family!
https://fsbckw.org/christmas
Dec. 24, 2024 | 5:00pm
Holiday Jazz in the Gardens
The Gardens Hotel at 526 Angela street welcomes holiday sprit seekers to enjoy festive outdoor jazz in its famous garden, with a full cash bar on site and a 20% Christmas discount on bottled wine and bubbly.
More info at: https://www.gardenshotel.com/
Dec. 25, 2024 | 10:00am – 12:30pm
Christmas Day Brunch Sail Aboard Schooner America 2.0
Enjoy Christmas morning the Key West way – sailing!
This 2.5 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!
Click https://sail-keywest.com/browse-by-theme/special-events/ for more info!
Dec. 29, 2024 | 5:00 - 7:00 PM
City of Key West Lighting of the Menorah Ceremony
Annual Lighting of the City Menorah Ceremony takes place at Bayview Park.
Dec. 31, 2024
Key West New Year’s Eve Celebrations
- Rooftop Conch Shell Drop – at Sloppy Joe’s, sloppyjoes.com
- Drag Queen Drop in a giant Red High Heal – at Bourbon St Pub, bourbonstpub.com
- Pirate Wench down the Schooner mast – at Schooner Wharf Bar, schoonerwharf.com
- Key Lime Wedge drop into giant Margarita – at the Ocean Key Resort Sunset Pier, oceankey.com/key-west-sunset-pier/
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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Key West “Bight” Before Christmas®.
info@dolphinecho.com for advertising or
to add a holiday event.
Photos by Rob O’Neal
