Pack your flip-flops. This holiday season, the Florida Keys & Key West invite visitors to unwrap the most festive time of year in true island style. From lighted boat parades and Santa sightings to quirky New Year’s Eve countdowns and fireworks, the holidays in the Keys are packed with tropical magic.
Here are some of the top events taking places across our stunning island chain:
HOLIDAY EXPERIENCES IN THE FLORIDA KEYS
Florida Keys Sea of Trees: Nov. 24 – Jan. 7
Featuring more than 100 beautifully decorated trees, the Florida Keys Sea of Trees event at The Protect Center in Islamorada also offers select evenings with Santa, snacks and cocktails, paint nights and more, all supporting the Dolphin ICU.
Holiday Lobster Trap Tree Lighting: Wednesday, Nov. 26
Honor Key West’s deep maritime heritage during the Holiday Lobster Trap Tree Lighting at the Historic Seaport. Decorated with twinkling lights, garland, red ribbons, and 45 lobster traps, this unique Christmas tree has become a beloved tradition in the destination.
3rd Annual Southernmost Turkey Trot 5K: Thursday, Nov. 27
Before the Thanksgiving Feast, the Southernmost Turkey Trot 5K (plus kid-friendly 1-Mile Rooster Romp) in Key West offers the chance to burn a few preemptive calories on a scenic run that benefits Reef Relief. At the finish line, enjoy a free, post-run mimosa.
Holiday Shopping Luxury Golf Cart Tour: Nov. 29-Dec. 20
Florida Keys Food Tour is launching its newest seasonal offering: the Holiday Shopping Luxury Golf Cart Food Tour in Islamorada, an elevated holiday experience that pairs island-inspired cuisine with boutique shopping — all while touring Islamorada aboard luxury golf carts.
Zonta’s Festival of Trees: Dec. 2-7
The Zonta Club of Marathon, a women’s service organization, presents fantastically decorated trees at its 15th annual Festival of Trees at Marathon Garden Club. This is a FREE event; just come and enjoy the sights.
Wesley House Family Services Holiday Village and BeLighted Bike Ride: Dec. 5
Wesley House Family Services kicks off the holiday season with a festive celebration at the Coffee Butler Amphitheater in Key West. The Holiday Village, with food trucks and rides is a family-friendly “pre-party,” for the BeLighted Bike Ride, which creates a luminous parade of holiday cheer along Whitehead and Duval Streets. Be part of this dazzling display by adorning your bike with festive lights and decorations!
Holiday Historic Inn Tours: Dec. 5 & 12
Explore beautifully decorated historic inns in Old Town Key West in the company of fellow holiday revelers while enjoying light sweet and savory treats as well as libations.
Islamorada Holiday Fest: Dec. 5
Kick off the holiday season at the 21st Annual Islamorada Holiday Fest at Founders Park. Featuring a 35-foot tree, the lively Holiday Parade (Friday, Dec. 5, 7:30 p.m.), and photos with Santa; this family favorite delivers small-town charm with tropical flair. The event’s star attraction, the Holiday Fest Snow Mountain, will again be made from 30 tons of the cold white stuff.
Islamorada Sailfish Tournament: Dec. 5-7
Reel in the ultimate gift! The first leg of the Florida Keys Gold Cup Championship trifecta, the 62nd Islamorada Sailfish Tournament this year features a new two-day fishing format with tournament activities based at Three Waters Resort and Marina. Unlimited anglers are allowed per boat. Visit islamoradasailfishtournament.com.
The Holidays at Lignumvitae Key Botanical State Park: Dec. 6
Discover the magic of Lignumvitae Key Botanical State Park off Islamorada at a holiday event including guided nature hikes, tours of the island park’s century-old caretaker’s home, storytelling presentations, 1930s-era games, seasonal live music, and an arts and crafts station.
Key West Christmas Parade: Dec. 6
Starting at 7 p.m., Duval Street bursts with holiday spirit as creative community floats, local marching bands, and costumed performers light up the night in the beloved Key West Christmas Parade, a joyful island tradition.
7 Mile SantaCon: Dec. 6
Dust off your Santa suit for a spirited day of poker, prizes, and holiday cheer at the 7 Mile SantaCon in Marathon, a fantastically Florida Keys take on the worldwide holiday celebration.
Old Town Trolley’s Holiday Sights and Festive Nights Tour: Dec. 8-23
Old Town Trolley’s popular green and orange trolleys, festively adorned with holiday lights, showcase Key West’s best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions.
Islamorada Junior Sailfish Tournament: Dec. 12-14
Catch the holiday spirit during The Florida Keys’ oldest sailfish tournament for kids age 16 and under celebrates its 61st year in 2025. Visit islajuniorsail.org.
Gay Key West Holiday Lights Trolley Tour: Dec. 13
Hop aboard for a glittering ride through Key West’s brightest holiday displays. The Gay Key West Holiday Lights Trolley Tour is a merry evening of jingle-and-mingle fun, complete with festive stops and community camaraderie.
2nd Annual Pigeon Key Holiday Spectacular: Dec. 13
Celebrate the season on historic Pigeon Key with a day of twinkling lights, snow machines, music, and visits from Santa as well as Mrs. Claus in this island-style wonderland.
Lighted Boat Parades: Dec. 13
Deck the hulls! Festively decorated vessels of all shapes and sizes illuminate the waters with holiday lights during the Key West Lighted Boat Parade (best viewed from the Schooner Wharf Bar) and the Key Largo Boat Parade (best viewed from the Caribbean Club and Sundowners).
A Positive Step 5K Rudolph Red Nose Run: Dec. 13
Don your holiday jammies, track shoes, and festive adornments to join in the A Positive Step 5K Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café in Key West. Race day check-in starts at 7 a.m. with an 8 a.m. start. After the race, enjoy refreshments, prizes and a silent auction.
Holiday Classic Car Show & Toy Drive: Dec. 21
Taking place in the Conch Republic Seafood Company parking lot on the Harbor Walk of Lights at Greene St. in Key West, the Holiday Classic Car Show & Toy Drive features classic cars from bygone days all decked out for the holidays. Attendees are encouraged to bring unwrapped toy donations.
Christmas Brunch Sail: Dec. 25
Set sail for a festive Christmas morning aboard the Argo Navis, a luxury 75-foot catamaran. During a two-hour Christmas Brunch Sail off Key West’s stunning coast, you’ll sip bottomless mimosas, savor local eats, and enjoy breathtaking ocean views.
FLORIDA KEYS HOLIDAY SHOPPING EVENTS
Black Friday Shopping Extravaganza: Nov. 28
Join the Key West Artisan Market, Truman Waterfront Farmers Market at for a day of unique gifts and handmade items made by local artists, crafters, and makers. Now in its fifth year, the Extravaganza has become an outdoor alternative to crowded stores and online shopping.
Lower Keys’ Island Art Festival: Nov. 29
In Big Pine Key, kick off the holiday shopping season at the Lower Keys Chamber of Commerce’s Island Art Festival. Find one-of-a-kind handcrafted items that typically include jewelry, stained glass, paintings, fragrant soaps, gourmet food; all created by talented regional artisans.
Key West Artisan Market: Nov. 30, Dec. 14, 21 & 28
A Key West holiday shopping tradition filled with one-of-a-kind gifts, the open-air Key West Artisan Market features local artists, authors, chef-made cuisine, craftspeople, performers, live music, and adult beverages.
Holiday Concert & Bazaar: Dec. 12
Join the Key West Art & Historical Society for the Holiday Concert & Bazaar, taking place on the historic porch of the Key West Museum of Art & History. The celebration features some of Key West’s finest artisans, musicians, and choirs.
NEW YEAR’S EVE, FLORIDA KEYS STYLE
- The Conch Shell Drop at Sloppy Joe’s: A Key West classic! Join thousands on Duval Street as the illuminated conch shell—the symbol of the Keys—descends to mark midnight at Sloppy Joe’s Bar.
- The Red High Heel Drop at Bourbon St. Pub: Watch glamorous performer Mulan Alexander descend 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: A truly unique seaport spectacle. Evalena Worthington, the Schooner Wharf’s iconic pirate wench, makes 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 on the beach.
- Key Largo Fireworks over Blackwater Sound: Celebrate with family and friends as fireworks light up the upper Keys in a dazzling display reflected across the water.
- Midnight Fireworks at Islamorada’s Founders Park: A family-friendly celebration in Islamorada where fireworks illuminate the sky above the waterfront, creating a picture-perfect start to 2026.
- Fireworks at Marathon’s Sombrero Beach: Gather in Marathon under the stars for a relaxed, coastal countdown where families can watch brilliant fireworks from the sand.
