18th Annual
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 18th 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

Advertisers

View Two Complete Holiday Event Calendars Below!

On the Historic Seaport Harbor Walk – Click for Info!
11-18-kwe-467x700

2023 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 2023 Updates!!

The 2023 Key West “Harbor Walk of Lights”TM

Celebrating the Maritime History of Key West

Wednesday, Nov. 22 – Free

The Lighting of the 2023 “Harbor Walk of Lights”

Lights come on at 6:00pm, holiday music starts at 5:00pm
This year featuring a SPECIAL Holiday display as a heartfelt salute to Jimmy Buffett!

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.

The official lighting is at 6pm, but at 5pm classic holiday music will start to fill the air. And for this SPECIAL year, Holiday music from Jimmy Buffett’s 2 Christmas albums will be mixed in with the traditional Christmas classics.

Stroll 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 3 blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport, the 2023 Key West “Harbor Walk of Lights” is destined to bring miles of holiday smiles to our One Human Family of visitors and locals alike.

Photos by Carol Tedesco & Rob O’Neal
kweornament2

Key West Express

Holiday Gifting the Whole Year Through

SAVE $66.00 roundtrip during this limited time holiday promotion, while supplies last.

Escape…Enjoy…Explore Key West with a gift that keeps on giving!
KW Express Travel vouchers are the perfect gift for any occasion.

Happy Holidays from Key West Express!

Friday, December 1 – January 15, Book Now!

Private Holiday Party Charter on Catamaran Echo

Private 2 hour Sail – Morning or Afternoon 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.

Friday, December 1 – FREE to Attend
6:00pm – 8:00pm

2023 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!

Photo Credit: Carol Tedesco

Saturday, December 2 – FREE

2023 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 3 – FREE to Attend

Schooner Wharf Bar 2023 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.

Saturday, December 9 – FREE

Schooner Wharf Bar & Galley and Absolute Vodka

32nd Annual Key West Lighted Boat Parade 2023

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!
Photos courtesy of Carol Tedesco

Saturday, Dec. 9

Schooner Appledore Lighted Boat Parade Party

7:30pm – 9:30pm

Be a participant in the 2023 The Lighted Parade aboard the Schooner Appledore II Parade Boat!
Trip Includes: Premium beer, boutique wines, wines and soft drinks. Very Limited Seating!

CHECK BACK for 2023 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.

Sunday, December 17 – FREE

The Florida Keys Southernmost Car Club presents

2023 Dick Moody “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!

Monday, Dec. 25

Christmas Day Brunch Sail 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!

wench2

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!

2023 Key West Holiday Fest

PLEASE CHECK BACK FOR 2023 UPDATES!

Click here for more KWHF info and 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 2023 Holiday Historic Inn Tour:
  • Night #1 – December 8
  • Key West Butterfly Conservatory
  • Wicker Guesthouse
  • The Mermaid & The Alligator
  • The Marquesa Hotel
  • Night #2 – December 15
  • Papa’s Pilar Distillery
  • Island City House
  • The Conch House Heritage Inn
  • The Lighthouse Inn

Tickets can be purchased by calling 305-296-4959 or online https://www.etix.com/ticket/online/viewPerformanceGroup.jsp?group_id=1527 any day prior to the date of the tour.”

Starting Nov. 24, 2023 (Sooner if we’re lucky)
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. 24, 2023 | 10:00am – 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. 27, 2023 | 6:00 – 7:30pm
Lighting of the City of Key West Christmas Tree

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

Nov. 28, 2023 | 5:30 – 9:30pm
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. 1, 2023
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:

https://www.wesleyhouse.org/belighted2023/

Dec. 1, 2023 | 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!

Click for more info and to see past pics!

Dec. 2, 2023 | 7:00pm
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. 3, 2023 | 4:30 – 6:30pm
Santa, Sweets, and Holiday Tree Lighting at the Key West Woman’s Club

Celebrate the season with the Key West Woman’s Club and Mayor Teri Johnston at the beautiful historic Hellings Curry Museum at 319 Duval St.

Enjoy appetizers, desserts, Amsterdam eggnog, and holiday music performed by the Bahama Village Children’s Choir and the Key West Community Orchestra. Donations of unwrapped, new clothing items for students K-12 are appreciated. More info. at 305-294-2039

Dec. 3, 2023 | Starts 6:00pm
Schooner Wharf Bar 2023 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. 3, 2023 | 7:00 – 9:00pm
Messiah Concert at Key West Methodist

Join us for the Messiah concert at Key West Methodist church
More info at: https://keywestumchurch.org/

Dec. 4 – 16, 2023
10th Annual POSH (Paws Often Steal Hearts)
Holiday events supporting the Florida Keys SPCA

Sunset Social Drinking Club’s annual holiday events to raise money for the FKSPCA.
Attend 2 gourmet dinners, a Phat Hat Concert on the water, the Annual POSH Gala, even a Doggie Day Sail and other fun fundraising events!
More info and tickets at:

https://www.poshkeywest.com/upcoming-events

Dec. 7, 2023 | 6:00 – 8:00pm
Sand Sculpture Christmas Tree Lighting

On the beach at The Reach Resort, 1435 Simonton Street, Key West.

Christmas Carole Sing Along and Holiday Cheer.

Bring an unwrapped toy to donate to The Boys & Girls Club of the Keys.

Dec. 8, 2023 | 5:00 – 9:00pm
7th 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: https://www.kwahs.org/education/bazaar

Dec. 8 – 23, 2023
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.

305-294-5161 http://www.conchtourtrain.com/

Dec. 8 – 23, 2023
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.

305-296-6688 http://www.trolleytours.com/

Dec. 9, 2023 | 10:00am – 2:00pm
10th Annual Parade of Paws

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

More info at: https://fkspca.org/event/10th-annual-parade-of-paws/

Dec. 9, 2023 | 12:00 – 3:00pm
Pet Pictures with The Grinch at the Hard Rock Cafe

Bring your critters for pet pictures with The Grinch.
Proceeds benefit River’s Wish, Inc., a 501(c)(3) non-profit senior dog sanctuary.

Dec. 10, 2023 | 10:00am – 3:00pm
The Key West Artisan Market, “Holiday Shindig on the Beach”

Shop for holiday treasures from local artisans while enjoying live music, tasty treats,
fun drinks, activities for the kids – including a ‘snowman’ building contest and even
a visit from old St. Nick. Southernmost Beach Resort, 1317 Duval St.

Dec. 10, 2023 | 1:00 – 3:00 PM
Monroe County Sheriff’s Office ‘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. 10, 2023 | 5:30 – 7:30pm
City of Key West Lighting of the Menorah Ceremony

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

Dec. 16, 2023 | 8:00am
15th 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. Early registrants receive a free t-shirt.

More info at: https://www.apsmc.org/annual-5k

Dec. 17, 2023 | 10:00am – 2:00pm
The Key West Artisan Market, “Holiday Shop Local” edition

Fine arts and crafts, jewelry, apparel, produce, delicious foods and more abound at this open-air bazaar.
Higgs Beach / Wildlife Center, 1801 White Street.

Dec. 17, 2023 | 11:00am – 3:00pm
The Florida Keys Southernmost Car Club
2023 Dick Moody “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. 24, 2023 | 5:00 – 7:00pm
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, 2023 | 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. 31, 2023 | 10:00am – 2:00pm
The Key West Artisan Market, “Bring in the New Year” edition

Fine arts and crafts, jewelry, apparel, produce, delicious foods and more abound at this open-air bazaar.
Higgs Beach / Wildlife Center, 1801 White Street.

Dec. 31, 2023
Key West New Year’s Eve Celebrations
COMING DECEMBER 2024
Nutcracker Key West

This semi-annual community production will be brought back to the stage in Key West in 2024. Our community’s talented children and adults along with 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: https://nutcrackerkeywest.com

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®.
info@dolphinecho.com for advertising or
to add a holiday event.

 

Photos by Rob O’Neal