Published on November 26, 2025
This holiday season, you can exchange the winter cold for the warm breezes of the Florida Keys. Plan a winter marine holiday and participate in a boat parade. After Christmas, you can enjoy Florida’s New Year festivities. The Florida Keys have a wide range of holiday products for visitors and residents alike. Enjoy the tropical holiday festivities.
Holiday Experiences in the Keys

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The Florida Keys Sea of Trees event runs from November 24 to January 7 at the Protect Center in Islamorada. Over 100 decorated trees will light up the center, complete with Santa visits, snacks, and cocktails to enhance the experience. For a festive touch, the Holiday Lobster Trap Tree Lighting on November 26 in Key West’s Historic Seaport honors the region’s maritime heritage with a display of twinkling lights on 45 lobster traps.
For active holiday-goers, the 3rd Annual Southernmost Turkey Trot 5K takes place on November 27 in Key West, followed by a kid-friendly 1-Mile Rooster Romp. The event benefits Reef Relief, making it a great way to stay fit while supporting a good cause.

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Between November 29 and December 20, the Holiday Shopping Luxury Golf Cart Tour in Islamorada pairs boutique shopping with island-inspired cuisine for an upscale holiday experience. If you’re looking to experience the local community spirit, the Key West Christmas Parade on December 6 bursts with vibrant floats, bands, and costumed performers along Duval Street.
Other notable events include the Islamorada Holiday Fest (December 5-6) featuring a 35-foot Christmas tree, a Holiday Parade, and a Snow Mountain, perfect for families. Additionally, the historic homes of Key West invite visitors to explore with the Holiday Historic Inn Tours (December 5 & 12), offering a peek into beautifully decorated historic inns with treats and festive drinks.
For a different take on holiday cheer, join the Lighted Boat Parades on December 13. Key West and Key Largo light up the waters with festive boats, creating a magical atmosphere for onlookers. The 2nd Annual Pigeon Key Holiday Spectacular on December 13 brings snow machines, music, and visits from Santa to this historic island.
New Year’s Eve in the Florida Keys
The Florida Keys bring in the New Year with unique celebrations. In Key West, the famous Conch Shell Drop at Sloppy Joe’s marks the countdown to midnight, while the Red High Heel Drop at Bourbon St. Pub offers a colorful LGBTQ+ celebration. For a more nautical experience, the Lowering of the Pirate Wench at Schooner Wharf Bar is a dramatic spectacle with cannon fire and cheers.
Key Largo also hosts a stylish New Year’s Eve celebration with a luxurious adults-only beachfront gala at Bungalows Key Largo. The event features gourmet dining, live music, and a fireworks display over Blackwater Sound to ring in 2026 with a bang.
Holiday Shopping and Special Events
For shoppers, the Florida Keys offer several unique opportunities. The Black Friday Shopping Extravaganza on November 28 at the Key West Artisan Market and Truman Waterfront Farmers Market features local gifts and handmade items. On November 29, the Lower Keys’ Island Art Festival in Big Pine Key showcases one-of-a-kind crafts and gourmet food. The Key West Artisan Market also hosts events on December 14, 21, and 28, offering art, local goods, and live performances.
For an unforgettable holiday experience, the Christmas Brunch Sail on December 25 aboard the Argo Navis, a luxury 75-foot catamaran, offers guests bottomless mimosas, local cuisine, and stunning ocean views.
Holiday Fun for All Ages
Families can enjoy events like the Wesley House Family Services Holiday Village and BeLighted Bike Ride on December 5, where kids and adults can decorate their bikes with festive lights and take part in a community celebration. Meanwhile, the Islamorada Junior Sailfish Tournament (December 12-14) offers young sailors the chance to compete in the oldest tournament for kids in the Florida Keys.
For those in search of more holiday magic, Islamorada’s Holiday Fest (December 5-6) and the historic Pigeon Key Holiday Spectacular (December 13) offer unforgettable family-friendly activities. Whether it’s snow machines, Santa visits, or local holiday traditions, these events provide plenty of fun and cheer.
Conclusion
That Florida Keys are amazing to spend holidays at. There are many activities to be part of. Traditions are nice to join in on. Is it holidays at Florida Keys with twinkling lights of boat parades? Fireworks on new year’s eve? Shopping, eating, and relaxing? Florida Keys bring warm memories to be cherished for a lifetime. Pack to your third year of holidaying at the Florida Keys. Don’t forget to pack shorts!

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Tags: boat parades, Florida Keys, Holiday Events, holidays, Islamorada

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Wednesday, November 26, 2025
Wednesday, November 26, 2025
Wednesday, November 26, 2025
Wednesday, November 26, 2025
Wednesday, November 26, 2025
Wednesday, November 26, 2025
Wednesday, November 26, 2025
Wednesday, November 26, 2025

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