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2021 Guide to Holiday Happenings in Key West
Oh, there's no place like Key West for the holidays, and there's no better place to enjoy the festivities and celebrations than right here with us. Holiday happenings across the island include holiday lights and sightseeing tours, parades by land and sea, burlesque shows, concerts, pool parties, bike parades, shopping, and more! Here is the lineup of events for the 2021 Key West Holiday Season:
The lighting of the Key West “Harbor Walk of Lights.”
Wednesday, November 24th | Lights come on at 6:00 pm, holiday music starts at 5:00 pm
The Holiday Season in Key West kicks off on November 24th with the Historic Seaport Lighting of the Key West "Harbor Walk of Lights." Just steps from our resort at the Harbor Walk, Green and Elizabeth Street, the official lighting of the 2021 Key West Harbor Walk of Lights takes place. Celebrate the Maritime history of Key West with the lighting of the Fishing Buoy Christmas Tree, a Nautical Christmas Tree, and the Lobster Trap Christmas Tree.
Stroll down the Harborwalk and enjoy the merry displays, including ship's anchors, tropical birds, tropical fish, manatees, and animated sea turtles all lit up.
The Harborwalk of Lights is lit every evening during the holidays!
BeLighted Bike Ride & Holiday Village
Friday, December 3rd, 4 pm - 8 pm | Holiday Shopping at the Village | Bike Ride starts at 8 pm
A fun family holiday event for all! The Holiday Village is a family-friendly pre-party to the BeLighted Bike Ride at the Coffee Butler Amphitheater in Truman Waterfront Park.
From 4 - 8 pm, the Holiday Village features 20+ holiday-themed booths providing free goodies for the kids, games, crafts, and giveaways! There are food vendors, a DJ, bounce houses, a "Best Bike" Contest, and of course, photos with Santa! Come early for your Santa photos. He will only be with us from 4:30 - 6:30.
The bike ride begins at 8 pm. Decorate your bike, dress up, and join us for the Key West BeLighted Bike Ride. The streets of Key West will glow as bikes are lit up to help gather needed toys for the struggling, working families of Key West for the holidays. Learn more about the BeLighted Bike Ride & Holiday Village.
Photo credit: Carol Tedesco
Key West Holiday Parade
Saturday, December 4th - Parade starts at 7 pm.
One of our favorite holiday parades is back! Join us for the City of Key West Holiday Parade on Saturday, December 4th, and find out why this is the best local parade of the year. Marching Bands, floats, school groups, trolleys, cars, bikes, and local businesses gather together to celebrate the holiday season. It’s one of our favorites for so many reasons, but most of all, it’s watching the children sit curbside with open eyes, waiting for Santa to make his debut. The parade route proceeds down Truman Ave to Duval, taking a right and continuing to Eaton Street.
The best viewing spots are along Duval Street and Truman Avenue.
KWAHS Holiday Concert & Bazaar
Friday, December 10th - 5pm - 9pm
Get into the holiday spirit with Key West Art & Historical Society’s Holiday Concert & Bazaar on Thursday, December 10th, from 5 PM to 9 PM, located on the beautiful historic porch and promenade of the Custom House Museum. It’s the big red brick building - you can’t miss it. The celebration will feature Key West artisans, musicians, and choirs, along with a spectacular holiday light show, with proceeds to benefit the Society's programs.
Visitors can browse hundreds of unique gift options at this signature holiday event while enjoying music, food, and libations to lift the frazzled ‘final shopping days’ spirits.
The Custom House is located at 281 Front Street, Key West. Learn more.
Photo credit: Key West Bight Before Xmas Celebration Facebook Page
Schooner Wharf Bar & Absolute Vodka 30th Annual Key West Lighted Boat Parade
Saturday, December 11th - Music at 6 pm, Parade starts at 8 pm.
Best viewing can be found all along the “Harbor Walk of Lights” at the Historic Seaport.
You don't have to go far to enjoy this parade! Right outside our resort is where you'll have the best viewing for the 30th Annual Lighted Boat Parade. The Key West Historic Seaport and harbor will light up as the decorated vessels from rowboats to tall ships and schooners set sail.
The Judges Stand is located at Schooner Wharf Bar, so hang out, grab a drink, enjoy the music and holiday festivities as the boats pass by in paradise. The parade begins at 8 pm, and the festivities start at 6 pm with live music and holiday happenings around the Historic Seaport. Learn more.
Shots & Photo Shots with Bad Santa
Sunday, December 12th, 6 pm - 8 pm | The Marker Key West Harbor Resort
Join Bad Santa at The Marker Key West Harbor Resort to celebrate an early Christmas. Do a shot with Bad Santa and get your photo taken by our professional photographer. Perfect for your Key West Christmas card! Drink Specials And More!
$5 donation for a professional picture. A portion of the night's proceeds will be donated to the Highgate Charitable Foundation; Aga Khan Foundation | Save The Children. Learn more.
Conch Tour Train and Trolley Holiday Lights Tour
December 12-17, December 20-23, December 26, 2021.
A must-see and do during the holiday season is Old Town Trolley's and Conch Tour Train Holiday Lights and Sights Tour. A great way to get in the spirit and see our island all decked out for the holidays. There will be caroling, apple cider and cookies, and complimentary magical viewing glasses. The Conch Tour Train Holiday Lights Tour is 60 minutes long and runs through December. We promise, you’ll have a holly jolly trolly time!
Adults : $26.25
Children - 3-12 years old. $15.75
Learn more about purchasing tickets and dates for the 2021 Holiday Lights Tour.
Sugar Rum Cherry: A Burlesque Nutcracker
December 15-17, Doors open at 7 pm. The show starts at 8 pm.
Head over to the Key West Theater on Eaton Street for a truly unique holiday burlesque version of The Nutcracker. Slip into your stockings and pull out your sugarplums for the outrageously cheeky production of Sugar Rum Cherry: A Burlesque Nutcracker. This naughty but nice two-act holiday reverie showcases a bevy of burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic. Doors open at 7 PM, show starts at 8 PM at the Key West Theater, 512 Eaton St. Tickets Available: $50 - $100. Learn more.
13th Annual 5k Rudolph Red Nose Run - the PJ Edition
Saturday, December 18th - 7 am - 10 am
Run for a good cause at the 13th Annual 5k Rudolph Red Nose Run to benefit for A Positive Step of Monroe County. Put on 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. Race day check-in begins at 7:00 am with an 8:00 am start time. After the race, enjoy refreshments, prizes, and a silent auction.
Location: Southernmost Beach Cafe, 1405 Duval Street | Key West, FL 33040
Sign up, register, and run with the locals and Rudolph to benefit this good cause! Learn more.
Where will you be on New Year’s Eve?
New Years Eve Around The World Party
Friday, December 31st, Noon - 9 pm | Southernmost Beach Resort
Head over to our sister property, Southernmost Beach Resort for the New Year’s Eve Around The World Party! There will be hourly drink specials starting at noon leading up to an early New Years’ Eve toast at 9 pm!
Southernmost Beach Resort, 1319 Duval Street, Key West, FL 33040
Photo: Rob O'Neal/Florida Keys News Bureau via AP)
Where will you be ringing in the New Year? At midnight in Key West, you have the opportunity to watch a Conch Shell Drop at Sloppy Joe's Bar, a New Year's Eve Shoe Drop by Sushi at the Bourbon Street Pub/New Orleans House complex or watch the Lowering of the Wench at Schooner Wharf Bar. So many options on one special night! Wherever you are, we wish you a safe and happy holiday season and a very Happy New Year!!
New Years Day Eve Take 2 Laser Night Pool Party
Saturday, January 1st, 6 pm - 9 pm | The Marker Key West Harbor Resort
Happy New Year! Let’s start the new year by the Seaport at The Marker Key West Harbor Resort. Join us for a night of music and a fantastic laser show while you swim the night away in one of our three pools. Papa’s Pilar will be there with drink specials and more!
What are some of your favorite holiday happenings where you live? We'd love to hear about them and see some of your festive photos. Enjoy the holiday season! #lovethemarker
November 01, 2022
It’s another one of our favorite times of the year; it’s stone crab season in Key West. October 15th marks the opening of the annual stone crab season and fishing companies can only catch Florida Keys stone crab between October...
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