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The Merriest Holiday Celebrations Across Southwest Florida

A Channukah party at Mercato, an illuminated stroll in Sanibel/Captiva and millions of lights at Naples Botanical Garden are just some of the things to see and do as part of your holiday bucket list.

BY November 23, 2021
Sleeping Santa
(Courtesy Third Street South)

Cue the festive tunes, and get ready to celebrate the holidays in true Florida style this winter, as all across Collier and Lee Counties groups deck out palm trees, lead community lightings and schedule surprise visits from Santa. There’s even some (faux) snow, courtesy of Third Street South in Naples, along with caroling, sightseeing and more jolly ways to ring in the season. One thing’s for sure: Southwest Florida sure knows how to throw a holiday party.  


Nov. 22 – Dec. 30  

Christmas on Third Naples  
Around these parts, the holiday cheer starts on Third Street South, which is among the first to debut its tree and lights. With the tree glowing, visitors can revel in faux snowfall, which starts around 7 p.m. nightly. Live music and decorated storefronts set the scene for photos with Santa. The jubilee continues from 5 to 8 p.m. every Thursday and Friday (excluding Dec. 24 and 31) throughout December. 


Nov. 26 – Jan 2 

Johnsonville Night Lights at Naples Botanical Garden 

For the 12th year, thousands of lights illuminate the pathways and greenery throughout the gardens. The nightly celebration features musicians, interactive light displays and other performances throughout the 170-acre oasis. While you’re there, grab a bite from Fogg Café, and pick up gifts for the nature-lover in your life at the gift shop on your way out. 


Nov. 26 – Jan 2 

Holiday Nights at Edison and Ford Winter Estates, Fort Myers 
Kick off the 46th annual celebration at the estates by watching the Edison team light their onsite 86-foot Mysore fig tree at 6 p.m on Nov. 26. During the illumination, there’s a choreographed light show that twinkles along to holiday tunes. Catch more light shows and family activities, such as visits from Santa and carolers, plus tours of the historic estate, through Jan.2. 


Nov. 28  

Chanukah Festival & Menora Lighting, Cape Coral  

Get the family to the Chabad of Cape Coral for this celebration that includes unique performances—including master bubble artist Blaise Reynolds from America’s Got Talent—along with a bounce house, face painting and traditional Hanukkah crafts and treats. Get there early to not miss the moment the group illuminates the six-foot-tall menorah. 


Nov. 29 

Chanukah Celebration at Mercato, Naples 

The Jewish Federation of Greater Naples hosts its Hanukkah celebration at 5 p.m. in Mercato. Come by for the menorah lighting and stick around for performances from Naples Klezmer Revival Band playing Hanukkah songs, craft tables and traditional Jewish treats. 


Nov. 29 – Dec. 31 

Gingerbread House at The Ritz-Carlton, Naples 

Each year the resort’s award-winning pastry team builds out a life-size gingerbread house in the lobby. Stop by on Thanksgiving Day to see the team in action, applying finishing touches with candy cane and gumdrop embellishments. While guests are discouraged from picking off the sweet structure, throughout the season, hotel staff doles out gingerbread cookies and hot cocoa to visitors. 


Nov. 30 – Dec. 19 

Trees & Teas Festival, Naples 
Sip teas from The Spice & Tea Exchange of Naples as you admire the festive trees—all uniquely decorated by local businesses—that fill the Sugden Community Theatre’s lobby for the holidays. You can also pick up a wreath during the event, with proceeds benefitting TNP programming. 


Dec 1 

Annual Holiday Stroll at Naples Design District 

Amble through the district and shop from nearly 30 art and design businesses. Each location offers a holiday cocktail from 4-8 p.m., plus stamps for your event “passport,” which enters you in a raffle. 


Dec 1 

Christmas Tree Lighting and Holiday Cirque Experience at Mercato, Naples

Watch the lighting of the largest Christmas tree in Southwest Florida during the Christmas Tree Lighting and Holiday Cirque Experience, with circus performers; Torrie, the world’s tallest elf, handing out magic glasses; and a show from Southwest Florida Symphony. 


Dec. 2-5  

2021 Festival of Trees at Sidney & Berne Davis Art Center, Fort Myers 

Join this 15th anniversary celebration with live music from Ben Allen Band, a rooftop wine and paint workshop—with stellar views of downtown—and seasonal trees decorated by local businesses. 


Dec. 3 and 4 

The Sanibel and Captiva Islands Luminary Stroll, Sanibel and Captiva Islands 

Sanibel and Captiva fill with music, lights and holiday cheer during the Luminary Stroll. Walk along the streets to browse decorated store fronts, take pictures with Santa and see a live nativity scene from Sanibel Community Church. 


Dec. 3 and 4 

Fifth Avenue South Tree Lighting, Naples 

Kick off the 48th annual tree lighting ceremony at 5 p.m. on Friday night in front of the Sugden Community Theatre. Then, walk along Fifth Avenue to find entertainment, including live music, a live nativity scene from the First Church of the Nazarene, as well as an ice-skating rink. The festivities continue from 10 a.m. to 10 p.m. on Saturday.  


Dec. 4 

Arts and Ends Holiday Sale and Craft Show, Fort Myers  

Peruse the booths at Alliance for the Arts from 9 a.m. to 1 p.m. to shop handcrafted gifts made by local artists and artisans. Alliance members receive a 10% discount. 


Dec 4   

The Nutcracker, Fort Myers  

Dancers from Gulfshore Ballet (mostly made up of students) and Gulf Coast Symphony come together to bring Tchaikovsky’s timeless holiday piece to life at Barbara B. Mann Performing Arts Hall. 


Dec. 7 

Fifth Avenue Christmas Parade, Naples 

March into the holidays with the Grinch and other festive characters that fill the nearly 80 floats in this show. The parade, which runs from 6 to 8 p.m., starts at Broad Street South and ends on Eight Street South. 


Dec. 11 

Naples Bay Christmas Boat Parade, Naples 

Decorate your boat and head for Naples Bay to make a splash on the water or watch the show from land at Naples City Dock, Landings Park, Bayview Park, various Tin City restaurants, Port O Call Marina, and at waterfront restaurants along the way. Boats depart at 6:15 p.m. from Naples City Dock and cruise until 8:30 p.m. 

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