Although lacking the snowy lawns and crisp weather for sweaters, the Gulf Coast bestows plenty of opportunities to experience the holiday spirit this December. In Naples, the Historic Palm Cottage toast to heritage and the city’s oldest home. In Bonita Springs, pianist Zachary Bartholomew honors a childhood holiday classic with an all-star trio. And in Fort Myers, dazzling displays compete at the Festival of Trees at Sidney & Berne Davis Art Center. Don’t miss this month’s holiday events. (For other December fun, check out our monthly digital blog.)
Through Dec. 21
Irving Berlin’s White Christmas at Gulfshore Playhouse
Although there’s no snow on the Gulf, Gulfshore Playhouse’s production of the beloved stage and movie musical brings the winter to the coast. Set to Irving Berlin’s classic score, the show follows two World War II veterans-turned-showmen and a sister act to Vermont, where the quartet attempts to save the inn of the gentlemen’s retired general. More than seven decades after its 1954 screen debut, the show remains a treasured staple of the Christmas season. Learn more.
Through Dec. 31
Festival of Lights at Fishermen’s Village, Punta Gorda
Punta Gorda’s waterfront shopping and dining hub transforms for the holidays, with more than 1 million lights strung along its decorated storefronts. Guests grab a meal at one of the destination’s dining establishments and stick around for music, dancing and visits with Santa. On December 20, the city’s annual boat parade illuminates its nearby winding canals. Learn more.
Through Jan. 4
Holiday Nights “Golden Jubilee” at Edison and Ford Winter Estates, Fort Myers
The historic setting celebrates the 50th anniversary of Holiday Nights, a seasonal staple drawing from Thomas Edison’s revolutionary invention to infuse the grounds with festive spirit. Thousands of lights and hundreds of historic decorations accentuate the nostalgic estate alongside rotating events like live entertainment, tours and the Children’s Tree Trail, featuring handmade ornaments from local students. Learn more.
Through Jan. 4
Johnsonville Night Lights in the Garden at Naples Botanical Garden
The lush 170-acre Naples Botanical Garden transforms into a twinkling winter wonderland this holiday season, with thousands of lights illuminating the foliage and walkways. Guests view the living bromeliad tree, feast on festive treats available in the garden’s Fogg Café and listen to live music as they celebrate winter the Floridian way. Learn more.
Dec. 2–24
Christmas at Palm Cottage, Naples
Naples’ 1895-constructed Historic Palm Cottage, the headquarters of Naples Historical Society, gets decked in garland and bows in an annual showcase to celebrate the season. It’s a celebration of Naples’ history and the heritage of its oldest house—a registered national landmark. Learn more.
Dec. 3
Leslie Odom Jr. — The Christmas Tour at Artis—Naples
After a sold-out performance in 2024, the Grammy Award-winning singer and actor—best known for his Tony-winning portrayal of Aaron Burr in Broadway’s Hamilton—returns to Naples with another unforgettable holiday concert. The film, television and Broadway star performs Yuletide classics, heartfelt originals and fan-favorite tunes from Hamilton. In September, Leslie reprised his iconic role for the groundbreaking musical’s 10th anniversary return to Broadway. Learn more.
Dec. 3
Holiday Stroll at Naples Design District
One of Southwest Florida’s creative quarters transforms for the holidays. From STARability Home Collection’s steaming cups of liquid nectar from their hot chocolate bar to crafting sessions at The Studio at The Collective, the best of Naples’ creative forces bring the community together. Learn more.
Dec. 3-7
Festival of Trees at Sidney & Berne Davis Art Center, Fort Myers
Lights twinkle, and ornaments of every shape, color and theme dangle from branches
decorated by local businesses at this annual event. A preview party on December 3 gets things started at the art center, and a wine and paint class the next evening tests budding artists’ creative talents. On Friday, the traditional wreath lighting ceremony spills out onto the front steps, followed by a downtown block party on Saturday. On the final day, guests vote on the best Christmas displays and enter a raffle for the chance to win a tree. Learn more.
Dec. 5
Ugly Sweater Cocktail Party at The Ritz-Carlton Naples, Tiburón
Within the serene, cherished walls of The Ritz-Carlton Naples, the Bella Vista Lounge invites guests to gather for spirited celebration with festive attire. The holiday cocktail party encourages people to taste specialty winter drinks, find their way to the dance floor and participate in an ugly sweater contest. Learn more.
Dec. 5
Movies in the Park at Riverside Park, Bonita Springs
Movies in the Park returns to Old 41 this month with a dusk showing of the Christmas classic: Santa Claus 2. Stretched on top of picnic blankets with loved ones, Riverside Park guests savor the free screening of the Tim Allen blockbuster underneath strings of lights as the movie plays from the massive screen—drive-in style. Learn more.
Dec. 5 and 6
Christmas In Naples on Fifth Avenue South, Naples
Locals assemble each year on Fifth Avenue South to enjoy a night of holiday festivities.
The tree-lighting ceremony kicks things off, with faux snow blanketing the avenue in winter wonder. With 20 restaurants serving dinner at this year’s event, including La Trattoria and Sushi-Thai, alfresco dining options flood the streets next to shopping opportunities at local vendor stalls. Learn more.
Dec. 9
Naples Annual Christmas Parade
Sleighbells ring and marching bands roar in this annual march through town. Beginning on the corner of Third Street South and Ninth Avenue South, the parade meanders through the streets of Naples before landing in front of City Hall. Spectators can witness the floats passing by from the Third and Fifth Avenue South hubs, enhancing their evening experience with nearby dining and shopping opportunities. Learn more.
Dec. 11
Zachary Bartholomew: Vince Guaraldi’s A Charlie Brown Christmas at Arts Bonita
Arts Bonita’s artist in residence turns to Vince Guaraldi’s timeless score in honor of the animated Peanuts film’s 60th birthday. Award-winning pianist Zachary Bartholomew, his all-star trio and guest vocalist Nicole Bartholomew pay tribute to the childhood jazz Soundtrack-turned-classic. The reimagining also educates attendees on Guaraldi’s life and iconic contributions to the film. Learn more.
Dec. 20 and 21
The Nutcracker at Barbara B. Mann Performing Arts Hall, Fort Myers
Gulfshore Ballet and Gulf Coast Symphony unite in an annual holiday performance of the more than 200-year-old story. Over the course of two nights, 90 dancers, nearly 50 musicians, 10 stagehands and dozens of youth performers take the stage amid elaborate sets and larger-than-life props, like a Christmas tree that grows from 10 to 30 feet tall. Learn more.
Dec. 26
Candlelight: Christmas Carols on Strings at Music & Arts Community Center, Fort Myers
The globally acclaimed Candlelight Concerts series presents a festive performance of Yuletide favorites. A local quartet performs symphonic renditions of tunes, like “O Holy Night” and “Deck the Halls,” among thousands of flameless candles in this intimate, immersive celebration of the season. Learn more.
Dec. 31
New Year’s Eve Celebration with Comedian Bobby Collins at Off the Hook Comedy, Naples
Best-selling author and Grammy Award-nominated comedian Bobby Collins, who has worked alongside industry titans like Chris Rock and Jerry Seinfeld, brings his national tour to Naples. Show-goers celebrate the comedy club’s 20th anniversary while ringing in the New Year and enjoying dinner options of pan-seared beef tenderloin, chicken rollatini, or shrimp and lobster alla vodka. For a special celebratory experience, the 8 p.m. show features a countdown to midnight to start 2026 off in high spirits. Learn more.