Spend the holiday season with friends and family exploring all that Key West has to offer! Monroe County residents can enjoy the Old Town Trolley tour for FREE when accompanied by a full fare adult paid guest with Hometown Pass.
The Wesley House Holiday Village & BeLighted Bike Ride is a family-friendly affair boasting an array of delights including Santa photos, engaging community booths filled with games and crafts for the kids, delicious food stalls, live music, and much more! At 8pm, join the other riders on their route down the iconic Duval Street. It’s an evening of festive cheer you won’t want to miss!
Key West Holiday Parade
Experience the ultimate holiday charm at the annual parade in the southernmost city of the continental U.S that delights locals and visitors alike. Kicking off at 7pm, the Holiday Parade features a variety of floats and local groups as they parade down White and Duval.
5:00 PM - 7:30 PM
Jazz in the Gardens!
Dates: December 3, 10, 17, 24, 31. Immerse yourself in an enchanting ambiance, surrounded by lush greenery and live jazz performances. Attend an unforgettable night of jazz this December!
10:00 AM - 3:00 PM
Mote Marine Laboratory's 2023 Ocean Fest
Truman Waterfront Park
Explore Mote’s Ocean Fest at Key West’s Truman Waterfront Park on December 3rd from 10 a.m. to 3 p.m. Enjoy a day of fun with crafts, games, live music, delicious food, and local brews, all in support of marine conservation. Meet scientists, discover exhibits, and learn how you can help protect our oceans. Join this exciting event celebrating and preserving our marine environment. All proceeds support coral restoration and research!
5:00 PM - 9:00 PM
Key West Art & Historical Society: Annual Holiday Concert & Bazaar
This popular holiday celebration offers a variety of mouthwatering food vendors, unique artisanal booths, and tons of local music. One of the evening’s highlights is the yearly holiday light show designed by Key West High School’s Conch 5 Studios that is projected onto the Customs House.
6:00 PM - 8:00 PM
Key West Lighted Boat Parade
Key West Bight and Harbor, 202 William St.
Get ready for Key West’s 32nd Annual Schooner Wharf Bar Lighted Boat Parade! The excitement starts at 6:00pm along the Harbor Walk with vibrant decorations and a local steel band playing lively calypso Christmas carols, setting the scene for a festive Caribbean-style celebration filled with infectious rhythms and holiday cheer.
10:00 AM - 2:00 PM
10th Annual Parade of Paws
Higgs Dog Beach
Come out and celebrate Key West’s furry companions this holiday season! Don’t miss a chance to support the local SPCA and see a delightful dog parade, a holiday bazaar featuring local artisan vendors, photo ops with Santa for your pups, live music, a Smooch-A-Pooch booth, and exciting raffles! It’s a wonderful celebration of our beloved tail-wagging community that you won’t want to miss!
12:00 PM - 3:00 PM
Pet Pictures with the Grinch
Hard Rock Cafe
Capture a memorable moment with your furry friends alongside the Grinch. For $20 per photo session, your critters can strike a pose with the Grinch himself!
The Studios of Key West: Ann Hampton Callaway
Enjoy a memorable evening listening to one of America’s most gifted artists in pop and jazz, Ann Hampton Callaway!
Fringe Theater: The Best Christmas Pageant Ever
In this heartwarming and spirited theatrical performance, witness the annual Christmas pageant take a delightful turn as the town’s young mischief-makers orchestrate a charming coup, showcasing the true spirit of Christmas. “The Best Christmas Pageant Ever” is a family-friendly play that offers a captivating story for all this holiday season!
5:00 PM - 6:00 PM
Key West Art & Historical Society: Happy Hour With the Historian
Comedy Key West, 218 Whitehead Street
This December, learn more about Florida’s enigmatic millionaire, Henry Flagler, and his industrious spirit that led to the creation of the Florida East Coast Railway’s luxury hotels. Join Dr. Cori Convertito as she dives into Flagler’s luxury hotels and what life was like for the East Coast Elite during the Gilded Age.
Key West Waterfront Winter Wonderland
Coffee Butler Amphitheater
This December, the Coffee Butler Amphitheater at Truman Waterfront Park transforms into a Key West Winter Wonderland, a magical holiday extravaganza for all ages! Experience the charm with an ice skating rink, thrilling games, rides, enchanting attractions, musical delights, dazzling light displays, and much more. Explore the vendor village filled with delectable food choices and unique creations from local artisans, making it the ultimate destination for festive fun and holiday shopping!
'A Positive Step' 5k Rudolph Red Nose Run
Southernmost Beach Cafe
Participate in a pajama-donned 5K this holiday season! In true Key West style, this 5K will award the most festive and most quirky pajamas. After the run, enjoy refreshments and a silent auction!
Key West Theater: Peter Mayer “Stars & Promises” Christmas Tour
Celebrate the holiday season with Peter Mayer, the acclaimed singer, songwriter, and guitarist, as he brings the 24th anniversary of his beloved “Stars and Promises” Christmas tour to Key West! Don’t miss this enchanting Christmas spectacle! Doors open at 6:30pm and the show starts at 7:30pm.
The Studios of Key West: MicroPARTY with Electric Blue Yonder
Get ready for the MicroPARTY, a live performance featuring the Electric Blue Yonder’s upcoming music, alongside a special sneak peek at unreleased animated music videos and exciting details about their next big adventure! This unique event promises a blend of music and fun suitable for both the young and the young at heart.
1:00 PM - 4:00 PM
Key West Home Tours: Holiday Style
Explore the charm of Key West’s most beautifully designed homes, where each stop is adorned in festive holiday décor. With Home Tour tickets, you can leisurely visit five homes at your own pace.