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Holiday Events Throughout Southwest Florida

Festive theater shows, boat parades and arts and crafts fairs bring the holiday spirit to the Gulf.

BY November 21, 2022
Sleeping Santa
(Courtesy Third Street South)

All across Southwest Florida, holiday celebrations light up the coast for the most wonderful time of the year. Events like White Christmas at the Broadway Palm Dinner Theatre, the Naples Holiday Boat Parade and Treasured Sounds of Christmas from the Charlotte Chorale bring merriment to the season, with a special Gulf twist. Here are some of the holiday events we won’t want to miss. 


Nov. 18-Dec. 30

Irving Berlin’s White Christmas at Broadway Palm Dinner Theatre, Fort Myers

Open the holiday season with the classic tale about two ex-soldiers who become business partners and follow a pair of singing sisters to a charming inn in Vermont, where antics ensue. Enjoy dinner at the theater, which is in its 29th season, while singing along to the show’s title track. 

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Nov. 21

Christmas on Third, Naples

Join the 45th-annual tree-lighting ceremony, where you’ll be greeted by a jolly Santa as he arrives on a vintage fire truck. Live music and sweet treats promise a good time. Visit the locale on Thursdays and Fridays at 7 p.m. for some faux snowfall throughout the month.

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Nov. 25-Jan. 1 (Closed Dec. 24 & 25)

Holiday Nights Celebration at Edison and Ford Winter Estates, Fort Myers

See the historic property illuminated by thousands of lights and holiday exhibits at this 47th-annual spectacular. Kids can visit with Santa, sing along with carolers and tour the homes, dolled up with festive decorations. 

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Nov. 27

Nutcracker! The Magic of Christmas Ballet at Barbara B. Mann Performing Arts Hall, Fort Myers

There’s nothing quite like The Nutcracker story to get you in the holiday mood. In its 30th-anniversary tour, the production features stars of the Ukrainian ballet joined by life-sized puppets and acrobatic routines, with extravagant costumes and sets. 

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Dec. 1

Holiday Taste of the Opera at Gulfshore Opera, Naples

Gulfshore Opera’s star performers command the room with their renditions of seasonal classics durin this this feast at The Club at the Strand. Book a table for four or six of your fellow music lovers. 

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Dec. 1-4

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

Local businesses design trees that are decked out in thematic splendor for this event that also includes a live auction, wine and paint session, and crafts for kids. Bring a toy donation, and you’ll get free admission. Proceeds benefit Goodwill Industries of Southwest Florida and the Sidney & Berne Davis Arts Center. 

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Dec. 2-3

5th Avenue Christmas Walk and Tree Lighting Ceremony

Naples’ Fifth Avenue transforms for the season with a two-day festival. Peruse the decorated streets, dine under baubles and garland, view a live nativity scene and meet Old Saint Nick. To keep up the holiday spirit, wander over to Third Street South on Thursdays and Fridays at 7 p.m. for some faux snowfall throughout the month.

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Dec. 3

Christmas Arts and Crafts Fair at University Village Shops, Fort Myers

Get all your holiday shopping done in one place as dozens of artisans and artists fill University Village Shops. 

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Dec. 3

Treasured Sounds of Christmas from the Charlotte Chorale, Punta Gorda

Charlotte Chorale sets the tone for the season with their concert of traditional and contemporary favorites, like “Journey of the Kings” and “Jingle Bells.” Don’t sleep on the silent auction. 

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Dec. 10

Naples Holiday Boat Parade

Boats sail around the Naples Bay, decorated with lights and seasonal garb. Park yourself in Tin City, at the Naples City Dock or other spots along the water to get a clear view of the parade. 

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Dec. 10-11

Bonita Springs Holiday of the Arts Festival

This festival brings artisans from across the country to Southwest Florida, with handmade ceramics, original paintings, textile arts and plenty of other giftable items. 

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Dec. 15-18

Holiday Pops with the Naples Philharmonic at Artis—Naples

Naples Philharmonic conductor Radu Paponiu leads this collaboration with Artis—Naples chorus groups. Free tickets are available for anyone who was impacted by Hurricane Ian. 

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Dec. 17

Winter Fest at Mercola Market, Cape Coral

Get out of the house for a day of holiday-filled activities. Fill your appetite with bites from food trucks as you browse the vendors and crafts from different artisans under festive Christmas lights. 

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Dec. 18

Christmas Fair at Bell Tower, Fort Myers

Bring out the family for a holiday celebration of crafts, artisans and food from local vendors at the open-air mall. 

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Dec. 21

Chanukah Celebration, Naples

Bring the family out for the Jewish Federation of Greater Naples’ festivities at Mercato on the Lawn. Light the menorah, gorge on Israeli food and listen to music from the Naples Klezmer Revival Band. 

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