Florida Keys Holidays to Shine with Lights and Subtropical Warmth

FLORIDA KEYS — Bright and beautifully “belighted” subtropical holidays in the Florida Keys & Key West are filled with warmth, inspiring good cheer throughout the 125-mile-long island chain. From Key Largo to Key West, the 2024 holiday season features spirited events such as lighted boat parades, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.

Select Keys holiday events are outlined below, while additional Florida Keys & Key West events can be found at fla-keys.com/calendar.

Nov. 23: Light Up Key Largo. Key Largo. Kick off the holiday season at Light Up Key Largo, an annual celebration sponsored by the Key Largo Community Preservation Foundation. The 15th annual family-friendly event features train rides, holiday vendors, games, food, treats, festive music, caroling and an appearance by Santa. Activities are set for 4-8 p.m., with the lighting of “Holly,” Key Largo’s 145-foot holiday tree, scheduled for just after dark at the Murray E. Nelson Government and Cultural Center, mile marker 102. Parking is available at Key Largo School with free shuttle service provided. Visit facebook.com/LUKLKEYLARGO/ or call 305-394-7530 or 904-463-0513.

Nov. 27: Lighting of the Harbor Walk of Lights. Key West. The Harbor Walk of Lights at the Key West Historic Seaport stretches along the harbor past Greene, William and Margaret streets to the Key West Ferry Terminal. Activities include lighting of a 20-foot-tall Fishing Buoy tree and a Key West Lobster Trap tree. Music begins at 5 p.m. beside the Fishing Buoy tree, with the lighting at 6 p.m. Music at the Lobster Trap tree is to begin at 6 p.m., with its lighting at 7 p.m. The displays will be illuminated nightly through Dec. 31. Visit keywestchristmas.org. 

Nov. 29-30, Dec. 5-6: Key West International Dance Co.: Fiesta de Navidad Tropical. Key West. Celebrate the season with Fiesta de Navidad Tropical, a lively holiday show featuring world-class Latin dance, vibrant costumes and festive energy. Audience members of all ages are invited to join the performers on stage and dance to live music. Performances begin at 8 p.m. at the San Carlos Institute, 516 Duval St. for tickets and information, visit kwinternationaldancecompany.com/fiesta-de-navidad.

Nov. 29: Black Friday Shopping Extravaganza. Key West. Join the Key West Artisan Market, Truman Waterfront Farmers Market and Shop Mom and Pop Key West vendors for a day of unique gifts and handmade items. Featuring local artists, crafters and makers, this event offers one-of-a-kind art, culinary delights and beverages at Truman Waterfront, 21 Quay Road. From 10 a.m. to 6 p.m., shoppers can enjoy a waterfront setting with views unlike any indoor mall. Visit facebook.com/events/1074747156827154.

Nov. 30: Lower Keys’ Island Art Festival. Big Pine Key. Get holiday shopping off to a great start 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 foodstuffs and more created by talented regional artisans. Enjoy live music and food throughout the event, slated for 9 a.m. to 3 p.m. on the Chamber of Commerce grounds, mile marker 31 oceanside. Visit lowerkeyschamber.com/chamber-events/.

Dec. 1, 15, 22 and 29: Artisan Market. Key West. A Key West holiday shopping tradition filled with one-of-a-kind gifts, the open-air bazaar is set for selected Sundays from 10 a.m. to 2 p.m. at 1801 White St. Markets feature Keys artists, authors, chef-made cuisine, craftspeople, performers, live music and adult beverages. Admission is free. Visit facebook.com/KeyWestArtisanMarket or call 305-509-3385.

Dec. 3-8: Zonta’s Festival of Trees. Marathon. The Zonta Club of Marathon, a women’s service organization, offers a free-admission display of decorated trees at its 14th annual Festival of Trees at Marathon Garden Club, 5270 Overseas Highway. View and bid to purchase decorated trees from 5-8 p.m. Tuesday through Thursday, 3:30-10 p.m. Friday and 10 a.m. to 8 p.m. Saturday. Kids can enjoy cookies with Santa and the Grinch Saturday from 10 a.m. to noon. Raffle tickets can be bought for a chance to win a tree, with a drawing for all trees at 8 p.m. Dec. 7.Visit zontaclubofmarathon.com or call 305-289-1221.

Dec. 5: Pet Pictures with Santa. Key West. Bring Fido, Fifi and the family for Pet Pictures with Santa, hosted by All Animal Clinic. Photos are taken from 6-8 p.m. at the nautical Christmas tree at the foot of William Street along the Key West Bight Marina/Harbor Walk of Lights. A $25 cash-only donation provides a professional high-resolution digital image, with proceeds benefiting the Boys & Girls Club of the Keys. Visit keywestchristmas.org.

Dec. 5-8, 13-15: Nutcracker Key West. Key West. Audiences can discover the Florida Keys’ seafaring heritage, coral reef environment and holiday spirit during eight performances of “Nutcracker Key West.” The production gives the classic ballet a unique twist, transforming the well-loved tale of a young girl's dream into a celebration of Key West's culture, traditions and underwater wonders. Showtimes vary at the Tennessee Williams Theatre, 5901 College Road. Visit nutcrackerkeywest.com for tickets and more information.

Dec. 6: Islamorada Holiday Fest. Islamorada. Kids can frolic on a 30-ton snow mountain during the 20th annual Holiday Fest, set for 4-10 p.m. on the Great Lawn at Founders Park, mile marker 87 bayside. Families can view the 6 p.m. lighting of a 35-foot-tall tree with snow blowing through its branches, enjoy holiday treats from Santa’s Sweet Shoppe, bid on Keys-crafted ornaments by 50 local artists during an online auction, shop at the Holiday Gift Bazaar and enjoy live performances. New this year is the Publix Holiday Sweet Shoppe featuring gourmet desserts, holiday cookies and seasonal giveaways. A variety of savory food will also be available. The holiday parade kicks off at 7:30 p.m. with Santa, antique cars, bands, and floats. Visit islamoradachamber.com/holiday-fest/ or call 305-664-4503.

Dec. 6: Wesley House Family Services Holiday Village and BeLighted Bike Ride. Key West. The annual family-friendly Holiday Village is set for 5-9 p.m. at the Coffee Butler Amphitheater at Truman Waterfront Park, 21 Quay Road, with community vendor booths, holiday-themed inflatable obstacle courses for kids, rides, food trucks, a “best bike” contest and photos with Santa. The bike ride, featuring a parade of bicycles decorated with holiday lights, leaves at 8 p.m. Tickets are $20 each (four for $70) for those age 4 and up, and free for kids age 3 and under. Visit wesleyhouse.org/events/belighted2024 or call 305-809-5000.

Dec. 6 and 13: Holiday Historic Inn Tours. Key West. Old Town Key West is filled with lovely historic inns, and two Friday evenings of 6-8 p.m. tours offer a chance to glimpse lavish decorations, discover unique architecture and experience holiday cheer and treats at featured properties. Visit keywestholidayfest.com for information and ticketing.

Dec. 7: Garden Club of the Upper Keys Holiday Market. Tavernier. Browse and shop from 9 a.m. to 4 p.m. in the club’s Holiday Garden filled with artists, artisans, plants and more. The market is held at 94040 Overseas Highway. Visit gardenclubupperkeys.org.

Dec. 7: Key West Hometown Holiday Parade. Key West. Holiday spirit is to fill the streets during the annual Key West Holiday Parade, showcasing the island city’s local charm with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade begins at 6:30 p.m. at Truman Avenue and White Street beside Bayview Park and proceeds down Duval Street. Seeing Santa is a highlight for kids. 

Dec. 8: Christmas on the Sheriff’s Animal Farm. Stock Island. Children and adults are invited to visit the unique Monroe County Sheriff’s Office Animal Farm for a special holiday open house from 1-3 p.m. It’s located just northeast of Key West at 5501 College Road. Holiday donations are encouraged. Call 305-293-7300 for more information.

Dec. 8: Eaton Street Christmas Stroll. Key West. Eaton Street becomes a southernmost North Pole Sunday, Dec. 8. Wander the blocks between Whitehead and Simonton from 3:30-7 p.m., stopping at venues including St. Paul’s Episcopal Church at 401 Duval St. for a traditional Christmas concert, and Tropic Cinema at 416 Eaton St. for some classic cartoons. The Studios of Key West hosts an open house at 533 Eaton St. during the stroll. Visit tskw.org/eaton-street-christmas-stroll. 

Dec. 9-23: Old Town Trolley's Holiday Sights & Festive Nights Tours. Key West. The 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. Tours depart each evening from Mallory Square at 6:30, 7, 8 and 8:30 p.m. Visit trolleytours.com/key-west/christmas-holiday-tours or call 855-623-8289 or 305-296-6688.

Dec. 9-10 and 13-23: Conch Tour Train's Holiday Sights & Festive Nights Tours. Key West. Lively Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 8 and 8:30 p.m. Included are holiday lights glasses as keepsake items. The hourlong tour, with holiday caroling, takes riders past the island's most elaborately decorated houses, buildings and neighborhoods. Visit conchtourtrain.com/key-west-christmas-holiday-tours/ or call 305-707-5775 or 305-296-6688.

Dec. 11: Gay Key West Holiday Lights Trolley Tour. Key West. Dress in festive gear and join the Holiday Lights Trolley Tour for a night of dazzling holiday displays around Key West. The event begins with a jingle-and-mingle at Bobby’s Monkey Bar at 5:30 p.m., with the trolley’s departure at 6:30 p.m. for a two-hour tour and a few merry stops. Participants are encouraged to bring holiday treats to share. The tour ends around 8:30 p.m. at Bobby’s. Registration is required. Visit facebook.com/events/918157406915499. 

Dec. 13: Key West Art & Historical Society: Holiday Concert & Bazaar. Key West. Join the Key West Art & Historical Society for the 7th Annual Holiday Concert & Bazaar set for 5-9 p.m. on the historic verandah and street in front of the Key West Museum of Art & History at the Custom House. This popular event features some of Key West’s finest artisans, musicians, and choirs, including live holiday music from the Bahama Village Music Program’s Joyful Voices Choir and House of Pan Steel Pan Drums ensemble. Attendees can also enjoy food, libations, and a holiday light show by Key West High School’s Conch 5 Studios, projected onto the exterior of the Custom House. The event is free and open to the public. 281 Front St. Visit kwahs.org/bazaar.

Dec. 13-14: Pigeon Key Holiday Spectacular. Marathon. The holiday season comes alive at Pigeon Key, the 5-acre island that lies beneath the Old Seven Mile Bridge, with a VIP viewing of the island’s holiday decorations Friday, Dec. 13. Saturday, the "Polar Express" begins running at 1 p.m., with trips throughout the day and into the evening. Families can spend a full day on Pigeon Key enjoying marine science activities, holiday food and drinks, guided tours, holiday-themed movies on the big screen, Santa encounters and snow. Admission is $5 for walkers and bikers. Tickets to ride the Polar Express are $10 in advance or $15 the day of the event. Call 305-743-5999 for information.

Dec. 13, 14, 15, 28: Lighted Boat Parades. Stock Island, Key Largo, Key West, Key Colony Beach, Little Torch Key. Festively decorated boats are set to cruise the waters around the Florida Keys, creating dazzling holiday spectacles. For details on the Stock Island Holiday Lighted Boat Parade (Dec. 13), visit keywestrotary.com. For the Key Largo Boat Parade on Blackwater Sound, themed “Christmas in the Keys” (Dec. 14), visit keylargoboatparade.com. For the Schooner Wharf Bar Lighted Boat Parade around the Key West Historic Seaport and harbor (Dec. 14), visit schoonerwharf.com. For the Key Colony Beach Christmas Boat Parade (Dec. 15), call 518-859-5662. For Kiki’s Sandbar Holiday Boat Parade and Drone Show on Little Torch Key (Dec. 28), call 305-780-7753.

Dec. 13-28: Waterfront Winter Wonderland. Key West. The Waterfront Winter Wonderland transforms the Coffee Butler Amphitheater at Truman Waterfront Park into a festive holiday experience for all ages. The family-friendly event features an ice-skating rink, rides like a Ferris wheel and carousel swings, games, live music, light displays and more. The amphitheater’s vendor village offers food and local artisan goods perfect for holiday shopping. Enjoy visits with Santa, a kids’ craft tent and festive celebrations. Admission is $12, with children 5 and under free. Additional costs apply for ice skating and rides. The fun takes place at 21 Quay Rd. Visit waterfrontwinterwonderland.com.

Dec. 14: A Positive Step 5K Rudolph Red Nose Run. Key West. Dress in festive holiday pajamas for the 15th annual A Positive Step 5k Rudolph Red Nose Run. Open to runners and walkers of all ages and abilities, the race starts and finishes at the Southernmost Beach Café, 1405 Duval St. Check-in begins at 7 a.m., with the race starting at 8 a.m. Registrants receive a free T-shirt. Visit apsmc.org  for information.

Dec. 19: Third Thursday Art Walk. Islamorada. Showcasing the area’s fine arts, music and culinary nuances, the Morada Way Arts & Cultural District features national and local artisans whose work is showcased in galleries along Morada Way between mile markers 81 and 82. Art Walks are held on the third Thursday of each month — and this 6-9 p.m. holiday edition features live music, local beer and wine and other seasonal cheer. Admission is free. Visit moradaway.org or call 305-664-2471.

Dec. 31: Key West New Year's Eve “Drops.” Key West. Ring in 2025 with a “conch shell drop” at Sloppy Joe's Bar, 201 Duval St.; the descent of a super-sized red high-heel shoe carrying a female impersonator at the Bourbon St. Pub/New Orleans House complex, 724 Duval St.; and the lowering of a pirate wench at midnight from atop a tall ship’s mast at the Schooner Wharf Bar, 202 William St. Revelers can also witness the “flight” of a uniformed “stewardess” in a section of a replica aircraft and enjoy a ticketed Gatsby-style party at First Flight Island Restaurant & Brewery, 301 Whitehead St. Visit sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest/ and firstflightkw.com.

Florida Keys events calendar: fla-keys.com/calendar/