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37 SWFL Holiday Events

Christmas tree lightings, Hanukkah festivities and yuletide concerts resound across the Gulf Coast.

BY November 15, 2023
Holiday Lights in palm trees
(Photo Courtesy The Lee County Visitor & Convention Bureau / by Chris Tilley Photography)

’Tis the season for eggnog and tinsel for a sunny winter. Throughout the region, festive celebrations foster gathering and good cheer for Southwest Florida peers. In Naples, embark on Fifth Avenue South’s 50th annual Christmas Walk, with plenty of polished restaurants to choose from.

 

In Fort Myers, Gulfshore Ballet’s professional dance company joins forces with Gulf Coast Symphony for a special performance of The Nutcracker. And in Charlotte County, menorah lightings and Chanukah activities unites the community. Don’t miss these joy-filled events. 

 

Nov. 16 — Dec. 17

Winter Wonderettes at Gulfshore Playhouse, Naples

A 1960s singing group works to save the magic of the holidays in four-part harmony with classic festive hits, as the storyline follows the disappearance of Santa Claus from a 1968 party at Harper’s Hardware. Find Out More

 

Nov. 24 — Dec. 16

Christmas Island Style, Marco Island

Find a slew of holiday activities on the island, including The Annual Tree Lighting and Community Celebration at Veterans Community Park on December 2. Pet and people parades, a holiday movie in the park, and cookies and milk with Santa at Mackle Park keep up the momentum to the grand finale—the sparkly Marco Island Annual Boat Parade on December 16.

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Nov. 24 — Dec. 31

Holiday Nights at Edison and Ford Winter Estates, Fort Myers

A festive, classic holiday tradition for nearly 50 years, the month-long occasion pays homage to Thomas Edison and Henry Ford with thousands of bulbs lighting up the historic riverfront homes and gardens. Period decorations reflect the turn-of-the-20th-century era when the Edisons and Fords wintered here. Special events include caroling concerts, holiday-themed guided tours and appearances by Santa and Mrs. Claus.

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Nov. 24 — Jan. 7

Johnsonville Night Lights in the Garden at Naples Botanical Garden 

Thousands of lights bring bursts of color and brightness to the garden for holiday season evenings, now with more dates than ever. Enjoy live music each night, photo ops, a bromeliad tree and holiday treats and drinks for purchase.

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Nov. 25

Lights, Camera, Christmas! at Gulf Coast Town Center, Fort Myers

Engage in ornament decorating, write letters to Santa and watch Cirque performers dazzle in a festive show. Catch the tree lighting at 6 p.m., and sip on hot cocoa for all the holiday goodness. For extra fun, bring a new, unwrapped toy or $5 minimum donation and take a picture with Mr. and Mrs. Claus or get your face painted.

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Nov. 28 — Dec. 17

A Sherlock Carol at Florida Repertory Theatre, Fort Myers

Charles Dickens meets Sir Arthur Conan Doyle in the regional premiere of the imaginative classics mashup. After the sudden death of the miserly Ebenezer Scrooge, a grown-up Tiny Tim calls upon detective Sherlock Holmes to solve the crime.

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Nov. 28 — Dec. 24

Ho! Ho! Ho! The Christmas Show at Players Circle Theater, Fort Myers

The theater company, created by area veteran producers Robert and Carrie Cacioppo, presents an original holiday comedy musical revue in its new space on McGregor Boulevard. Inspired by holiday TV specials of yore, it tells the stories behind the classic carols folks grew up loving.

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Nov. 29 — Dec. 23

Snowbird Follies at Music & Arts Community Center, Fort Myers 

The whimsical yuletide concert sees the Gulf Coast Symphony perform a playful tribute to Fort Myers’ original snowbirds, Thomas Edison and Henry Ford. Tap your toes to holiday favorites spiced with local history. 

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Nov. 30 — Dec. 3

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

In its 17th year of benefitting Goodwill Industries, the festival returns with viewing and voting for trees decorated by local businesses. A wreath lighting, live concert and Santa block party fill the days until the raffle drawing for the lucky ones who will take home the decorated trees. 

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Nov. 19 — Dec. 31

Festival of Lights at Fishermen’s Village, Punta Gorda 

Following the lighting ceremony on November 18, where more than a million lights illuminate the riverfront shopping and entertainment center, the festival features live entertainment and drop-ins from Santa Claus and The Grinch. King Fisher Fleet offers its traditional Christmas Light Canal Cruise around Punta Gorda throughout the month. Activities culminate with a New Year’s Eve celebration and fireworks. 

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Dec. 1

Annual Bell Tower Tree Lighting & Luminary Extravaganza

At this family Christmas festival, Santa Claus, arriving in style on a South Trail Fire Department fire truck at 6:30 pm, headlines the event with a magical tree lighting ceremony. The evening unfolds with live music by a live emcee and DJ, a bounce house, face painting, balloon artists, and locally rescued reptiles from Adam’s Animal Encounters. Capture memories at themed photo booths. 

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Dec. 1-30

Christmas at Historic Palm Cottage, Naples

With the circa 1895 cottage and Norris Gardens all aglow with lights and deck-the-halls period decorations, Naples’ oldest home exudes timeless holiday cheer. Follow your pre-reserved, 45-minute cottage tour with a leisurely stroll around the property. 

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Dec. 2

Fort Myers Beach Christmas Boat Parade

The 35th annual lighted boat parade departs from Salty Sam’s Marina and travels throughout Estero Bay. Boaters join the festivities, and spectators watch the twinkly spectacle from restaurants in the back bay area. Vote for your favorite decorated vessel online for the People’s Choice Award.

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Dec. 2

Holiday Festival of Lights at Cape Coral Parkway, Cape Coral

The more than 30-year-old annual celebration opens by welcoming jolly ole Saint Nick to the festivities for the official lighting of the 26-foot tree in Big John’s Plaza. The Tiny Tots Train welcomes all littles aboard for a ride around Snowcap Square and through the inflatable Candy Cane Park. Local musicians and dance troupes and other entertainers keep up the holiday spirits throughout the event.

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Dec. 2-17

Festive High Tea at The Ritz-Carlton, Naples

On select dates throughout the two weeks, the long-running holiday tradition takes place in the new Lobby Bar, featuring savory and sweet treats with high tea sophistication and the hotel’s trademark elegance. 

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Dec. 5 

Naples Christmas Parade

Downtown Naples holiday celebrations kick off with a traditional parade of floats, school bands, civic groups and Santa Claus through Fifth Avenue South and Third Street South.

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Dec. 5 

José Feliciano: Feliz Navidad at Seminole Casino Hotel, Immokalee 

At 78 years old, the nine-time Grammy Award-winning Puerto Rican singer and composer of “Feliz Navidad” fame rocks the stage. Recognized as the first Latin artist to effectively cross over into the English music market, his music fuses Latin, blues, jazz, soul and rock genres, accompanied by his signature acoustic guitar.

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Dec. 6

Holiday Stroll in Naples Design District

For the seventh annual event, guests meander through the heart of the Naples Design District to shop, dine and browse participating galleries—sipping cocktails and holiday beverages along the way. Live music, a fashion show, yoga classes and train displays add to the special sales and promotions shops and restaurants offer that day. 

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Dec. 7

Traditional Holiday Stroll on Third Street South, Naples

The neighborhood and holiday revelers dress festively for this evening of cheer. Carolers, sparkling lights, dazzling decorations and fun special promotions make it the perfect time to get in the spirit and start on your Christmas list. Restaurants offer special Holiday Stroll cocktails and menus.

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Dec. 7-10 

A Christmas Carol: A Live Radio Play at Arts Bonita

The Dickens classic gets a 1940s refresh staged as a radio broadcast. A handful of actors bring ghostly spirits, the Cratchit family and Ebenezer himself to the stage, interspersed with period commercials for fruitcake and enhanced with live-radio sound effects and musical scoring. 

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Dec. 7-10

Irving Berlin’s White Christmas: The Musical at Fort Myers Theatre

The well-loved 1954 movie starring Bing Crosby, Danny Kaye and Rosemary Clooney translates smoothly to the stage, featuring its eponymous, timeless Christmas song, along with Berlin’s “Blue Skies,” “I Love a Piano” and “How Deep Is the Ocean.” The musical follows the post-World War II antics and romance of two performing vets and a sister singing duo to the snowy setting of a Vermont lodge. 

Find Out More   

 

Dec. 7-15

Chanukah at Chabad of Charlotte County

The local Chabad celebrates the third, fifth and seventh nights of Chanukah at locations throughout the county with Menorah lightings, live music and, of course, food. Traditional Chanukah dishes served include donuts, latkes, chocolate gelt and kosher Chinese. 

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Dec. 8 and 9 

Fifth Avenue Christmas Walk and Tree Lighting Ceremony with Avenue Dining, Naples

Fifth Avenue South brightens the holidays with a tree lighting in Sugden Plaza in this 50th annual event. Alfresco dining at more than 15 restaurants up and down Fifth Avenue South adds a culinary flair to the festivities; reservations required. Meet Santa, skate on the ice rink, experience a live nativity by the First Church of the Nazarene and shop “the Ave,” which is closed to vehicular traffic the two days of Christmas Walk.  

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Dec. 8 and 9

It’s a Wonderful Life: Live Radio Play at Cambier Park

The Naples Players present this adaptation of George Bailey’s holiday dilemmas as a live 1940s radio broadcast. The al fresco presentation provides no seating; attendees should bring their own chairs or blankets.  

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Dec. 8-17

Yippee Ki-Yay Merry Christmas! A Die Hard Musical Parody at The Laboratory Theater of Florida, Fort Myers

Based on the Bruce Willis film series, the musical adaptation follows New York police officer John McClane, who fights his way home to his estranged family. Making its regional premiere, the parody brings mirth and satire to the holiday season. 

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Dec. 9-11

Southwest Florida Symphony: Holiday Pops – Santa’s Serenade, Bonita Springs and Fort Myers

Maestro Andrew Lipke conducts and performs a brave new interpretation of holiday classics, blending traditional themes with new lyrics. His unforgettable journey travels to Fort Myers Senior High School, First Presbyterian Church of Bonita Springs and Village Church at Shell Point in Fort Myers. 

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Dec. 10

Sarah Brightman: A Christmas Symphony at Artis—Naples

The legendary soprano and original Christine Daaé in Andrew Lloyd Webber’s The Phantom of the Opera stops in Southwest Florida as part of her annual holiday tour. The singer’s three-plus-octave vocal range expands throughout Hayes Hall. Accompanied by orchestra, choir and special guests, A Christmas Symphony has become an annual Artis—Naples tradition. 

Find Out More 

 

Dec. 11

Community-Wide Chanukah Celebration at Mercato, Naples

On the lawn at Mercato, join live entertainment, rabbis and clergy for the lighting of the Menorah. The free event features the Naples Klezmer Revival Band and Israeli food for purchase, plus balloon creations and other activities. 

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Dec. 14–17

Naples Philharmonic: Holiday Pops at Artis—Naples

Popular season two American Idol alumnus Clay Aiken joins the Naples Philharmonic, Naples Philharmonic Chorus and Naples Philharmonic Youth Chorus for this year’s lineup of holiday musical favorites. Among his collection of top-charting albums, Aiken has released two Christmas albums and, in 2004, produced and starred in the TV special A Clay Aiken Christmas.

Find Out More 

 

Dec. 14-31

ELF The Musical at Fort Myers Theatre

The classic holiday movie hits the stage in this performance and adds a musical score to the story of Buddy, the orphaned human who is raised by the elves. Once grown up, Buddy sets out on a mission to discover his father’s identity and in doing so, serendipitously brings Christmas magic to New York City.

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Dec. 15

Candlelight Christmas Carols at Cambier Park, Naples

Local musicians perform in the bandshell as families enjoy food truck treats and beverages and sing along to classic yuletide carols by flameless candlelight under the stars.

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Dec. 15–17 

Home for the Holidays at TheatreZone, Naples

TheatreZone’s beloved seventh annual spectacular features the professional cast, along with 10 children from Community School of Naples and a seven-piece band, showcases the appeal and power of holiday music through song and original choreography. New numbers this year include “Christmas Morning Feeling” from the movie Spirited, “Disco Santa” and a Blake Shelton-Gwen Steffani duet, “You Make it Feel Like Christmas.”

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Dec. 16

The Nutcracker at Barbara B. Mann Performing Arts Hall, Fort Myers

Gulfshore Ballet joins the Gulf Coast Symphony to reinterpret Tchaikovsky’s sugar-plum dream world. Based on a holiday story about a family’s Christmas Eve celebration, it introduces new choreography reimagined by Gulfshore Ballet artistic directors Ileana Lopez and Franklin Gamero

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Dec. 20-22

Naples Ballet Presents The Nutcracker at Artis—Naples

The children’s ballet company pairs the evergreen tale to a symphonic score performed by the Naples Philharmonic. The holiday show is a cherished favorite and is sure to spark a festive tradition for Southwest Florida families.

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Dec. 23

Holiday on the Bay at the Village Shops on Venetian Bay, Naples

Everything you’d expect from a traditional holiday celebration—even snow—happens at the Village Shops. Dickens Period Carolers perform, Santa and Mrs. Claus show up, and shops and restaurants put forth their glad tidings. Kowiachobee Animal Preserve adds furry and reptile friends—from domestic to exotic animals—to the mix. 

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Dec. 24-25

Christmas at Luminary Hotel & Co., Fort Myers

Enjoy holiday feasts on Christmas Eve and Christmas Day from the hotel’s various eateries. Festive holiday cocktails are available at Beacon Social Drinkery on Christmas Eve; Oxbow Bar & Grill 

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Dec. 29 

NUTCRACKER! Magical Christmas Ballet! at Barbara B. Mann Performing Arts Hall, Fort Myers

Catch this nationally touring show in one of two performances to experience the international talents of the troupe, like Ukrainian principal artists, in this acrobatic interpretation of the European story and the Russian score. Handmade costumes, 10-foot tall stage puppets, hand-painted sets and 40 professional ballerinas come together to create an enchanting holiday story.

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