What’s Happening in the Florida Keys for the Holidays and New Years

It’s time to swap winter scarves and boots for tank tops and flip flops as the Florida Keys & Key West invites travelers and locals to celebrate the holidays in true island style.

From lighted boat parades and Santa sightings to quirky New Year’s Eve countdowns and fireworks, the holidays are packed with tropical magic.

Holiday Experiences

• Florida Keys Sea of Trees (November 24 – January 7) features more than 100 decorated trees at The Protect Center in Islamorada on select evenings with Santa, snacks, cocktails, and paint nights, supporting the Dolphin ICU. 
• Holiday Lobster Trap Tree Lighting (November 26) as Key West’s historic maritime heritage is honored during this event at the Historic Seaport with twinkling lights, garland, red ribbons and 45 lobster traps.
• 3rd Annual Southernmost Turkey Trot 5K (November 27) plus kid-friendly 1-Mile Rooster Romp in Key West on a scenic run benefiting Reef Relief. 
• Holiday Shopping Luxury Golf Cart Tour (November 29-December 20) in Islamorada, features an elevated holiday experience pairing island-inspired cuisine with boutique shopping.
• Zonta’s Festival of Trees (December 2-7) sponsored by a women’s service organization presents a free event with beautifully decorated trees at Marathon Garden Club.  
• Wesley House Family Services Holiday Village and BeLighted Bike Ride (December 5) features bikes adorned with festive lights and decorations, kicking off at the Coffee Butler Amphitheater in Key West.
• Holiday Historic Inn Tours (December 5 & 12) explores beautifully decorated historic inns in Old Town Key West with holiday revelers, sweet, savory treats and libations. 
• Islamorada Holiday Fest (December 5-6) features a 35-foot tree, a Holiday Parade and Holiday Fest Snow Mountain. 
• Islamorada Sailfish Tournament (December 5-7) is the first leg of the Florida Keys Gold Cup Championship trifecta with a new two-day fishing format that includes tournament activities at Three Waters Resort and Marina.  
• The Holidays at Lignumvitae Key Botanical State Park (December 6) brings the magic of Islamorada with guided nature hikes, tours of the island park’s century-old caretaker’s home, storytelling presentations, 1930s-era games, seasonal live music and arts and crafts.
• Key West Christmas Parade (December 6) on Duval Street bursts with holiday spirit with community floats, local marching bands and costumed performers.
• 7 Mile SantaCon (December 6) sports a spirited day of poker, prizes, and holiday cheer at the 7 Mile SantaCon in Marathon.
• Old Town Trolley's Holiday Sights and Festive Nights Tour (December 8-23) features adorned green and yellow trolleys with holiday lights and Key West's best-decorated neighborhoods on fun-filled 60-minute excursions. 
• Islamorada Junior Sailfish Tournament (December 12-14) is The Florida Keys’ oldest sailfish tournament for kids age 16 and under.
• Gay Key West Holiday Lights Trolley Tour (December 13) offers a glittering ride through Key West’s brightest holiday displays with festive stops and community camaraderie. 
• 2nd Annual Pigeon Key Holiday Spectacular (December 13) on historic Pigeon Key celebrates the season with twinkling lights, snow machines, music, and visits from Santa and Mrs. Claus.
• Lighted Boat Parades (December 13) where festively decorated vessels illuminate the waters with holiday lights during the Key West Lighted Boat Parade and the Key Largo Boat Parade.
• A Positive Step 5K Rudolph Red Nose Run (December 13) where participants don holiday jammies, track shoes, and festive adornments in Key West.  
• Holiday Classic Car Show & Toy Drive (December 21) at the Conch Republic Seafood Company parking lot on the Harbor Walk of Lights at Greene St. in Key West features classic cars from bygone days decked out for the holidays, and gifted unwrapped toy donations. 
• Christmas Brunch Sail (December 25) aboard the Argo Navis, a luxury 75-foot catamaran. The two-hour sail offers bottomless mimosas, local eats and breathtaking ocean views. 

Holiday Shopping Events 

• Black Friday Shopping Extravaganza (November 28) at the Key West Artisan Market and Truman Waterfront Farmers Market with gifts and handmade local items. 
• Lower Keys’ Island Art Festival (November 29) held in Big Pine Key with one-of-a-kind handcrafted items, artwork and gourmet food.
• Key West Artisan Market (November 30, December 14, 21 & 28) filled with local artists, authors, chef-made cuisine, craftspeople, performers, live music, and adult beverages.  

New Years Eve Celebrations

• The Conch Shell Drop at Sloppy Joe’s: A Key West classic! descends to mark midnight at Sloppy Joe’s Bar.
• The Red High Heel Drop at Bourbon St. Pub as performer Mulan Alexander descends in a sparkling red high heel as Key West’s LGBTQ+ community rings in 2026 with flair, music, and joy.
• The Lowering of the Pirate Wench at Schooner Wharf Bar is a seaport spectacle with Evalena Worthington, the Schooner Wharf’s pirate wench, making her dramatic descent from a tall ship’s mast amid cannon fire and cheers.
• Key Largo New Year’s Celebration, a luxurious adults-only beachfront gala at Bungalows Key Largo, featuring gourmet dining, live performances, and fireworks.
• Key Largo Fireworks over Blackwater Sound where fireworks light up the upper Keys in a dazzling display across the water.
• Holiday Concert & Bazaar (December 12) on the historic porch of the Key West Museum of Art & History featuring artisans, musicians, and choirs.

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