Pensacola Magazine

Holly Jolly Holiday Performances

It’s that time of year when our downtown streets are lined with twinkling lights, and holiday cheer is found around every corner. Luckily, residents and visitors alike are in for plenty of exciting holiday performances and events this year. Here are just a few of the festivities that will be filling our town with good tidings this holiday season.

The Nutcracker presented by Ballet Pensacola

December 15, 16 & 17

Ballet Pensacola will bring its highly anticipated performance of The Nutcracker to the stage of the historic Pensacola Saenger this December.

Twenty-one professional ballet dancers and more than 100 Ballet Pensacola students will take you on this riveting adventure with enchanting costumes and set designs from costume designer Tiffany Nichols and production and technical manager Dominic Krippes.

Ballet Pensacola Artistic Director, Darren McIntyre, brings together breathtaking choreography alongside Tchaikovsky’s spectacular musical score to bring The Nutcracker to life. The audience will find themselves in a dream-like state with the little details Ballet Pensacola has incorporated into this production.

“Many hours of perfecting shapes and patterns, strengthening technique, building stamina and developing artistry goes into the rehearsal process, with each artist striving for personal bests, so by the time we reach the magic of the theatre, it all looks effortless (and) beautiful, and we perform with ease and grace,” McIntyre said.

The evening performances of The Nutcracker will showcase Connecticut native Hannah Holtsclaw as Clara for her sixth season with Ballet Pensacola and Felipe Zapiola from Salta City, Argentina as the Prince. The stars of the matinee performances are Destin native Savannah Crabtree and Juan Arango from Medellin, Colombia.

“Dancing allows us to do what we love and sharing that with the community and our audiences is something that we all cherish. The memories created are invaluable,” McIntyre said, regarding the intensity and passion that Pensacola’s ballet dancers demonstrate.

A full cast listing can be found on their website at Performances of The Nutcracker will be held on December 15, 16 and 17 at the Saenger Theatre at 118 South Palafox Street in downtown Pensacola. Tickets range from $45 to $75 and can be purchased online at or in-person at the Saenger Theatre Box Office located at 22 E Intendencia Street.

Sugar Plum Fairy Experience

December 15, 16 & 17

Oyster Bay Boutique Hotel has collaborated with Ballet Pensacola, Reboot and Classic City Catering to deliver a magical and unforgettable Nutcracker experience to a few lucky guests over the weekend of The Nutcracker performance. They will be welcomed into the hotel with a one-night stay, two tickets to Ballet Pensacola’s The Nutcracker and an additional brunch. There is an option for just the ballet and brunch, which will include holiday activities for children and holiday shopping. Holiday surprises will be exhibited throughout the day of guests’ stay. The one-night stay will be available for either Friday, December 15 or Saturday, December 16. Brunch times differ each day. Visit for more information.

Winterfest 2023

Through December 24

Winterfest is back in action this year with its popular line up of holiday tours, parades, photo ops and more until the night before Christmas. Hop on a festive trolley and follow the Christmas spirit with the Grinch, the Polar Express and Ebenezar Scrooge. The Grinch himself constructed a brand-new trolley this year made from Whoville’s trash to bring you along to the annual Whobilation. The Scrooge Tour will have you follow Scrooge on an adventure to Christmas Past, Present and Future with a few more ghosts along the way, and the Polar Express Tour will have you dancing in your seat with steaming hot chocolate and believing in Christmas magic. Snap a few photos with Santa Claus after you tell him your Christmas wishlist and snap some with the Grinch—but be careful! If you tell him what you want for Christmas, he might just snatch it from under your tree. For more information and ticket purchases, visit

Pensacola Beach Lighted Boat Parade

December 2

The Pensacola Beach Chamber is hosting its annual Lighted Boat Parade located at the Santa Rosa Sound on December 2 at 6:30 pm. Boats will set sail from the Sabine Marina, make their way around to Quietwater Beach and circle back to the marina. A kids’ holiday party will be held just before the boat parade at Shaggy’s on Pensacola Beach. Spectators can watch, either from the Sabine or the boardwalk. Boats can be any size, shape or color and can compete for “most merry” and “best of show” awards during the parade. Visit for more information.

The Prophecy Show presents Music of Trans Siberian Orchestra

December 2

The Prophecy Show is once again bringing the city of Pensacola a night of holiday rock opera as the longest-running and most popular tribute to the Trans Siberian Orchestra. The group will bring jaw-dropping costumes, lasers, fog and choreography to the historic Pensacola Saenger Theatre that are sure to have audiences mesmerized. The show will take place on December 2 at 7:30 pm. Tickets can be purchased online at, or in-person at the Saenger Theatre Box Office. For complete show details, visit

Jackson’s Steakhouse presents Deck the Halls: A Holiday Event

December 2, 9 & 16

Back by popular demand, Jackson’s Steakhouse will return with its popular Deck the Halls Holiday Event, with reservations available for three different Saturdays in December. Seating times will be at 10:30 am and 1 pm. Jackson’s has partnered with Pensacola Opera to fill the restaurant with costumed carolers singing all of your Christmas favorites. Patrons will be serenaded with classics like, Silent Night, We Wish You a Merry Christmas, Away in a Manger and more. Joseph Decker, Tina Wang, Greg Watson and Suzette Leger will serve as the featured carolers of the evening. Jackson’s head chef, Chef Miller, will offer the full lunch menu as well as an additional holiday feature for the occasion. For details and to make reservations, visit

Pensacola Children’s Chorus presents Christmas on the Coast

December 8, 9 & 10

The Pensacola Children’s Chorus will host its dazzling annual holiday concert, Christmas on the Coast, at the Pensacola Saenger Theatre December 8 through 10 with showtimes at 7:30 and 2:30 pm. This heart-warming show will be sure to lift your spirits and bring you hearty laughter as talented singers sing your favorite Christmas tunes and touch on the chaotic side of Christmas–ugly sweaters, regifting, last-minute shopping and everything in between. For more information, visit or

Cox Pensacola Christmas Parade

December 9

The Cox Pensacola Christmas Parade is celebrating its 41st year on Saturday, December 9 at 5:30 pm in downtown Pensacola. Featuring more than 50 dazzling holiday floats and performances by high school marching bands from Escambia County and Pace and Milton High Schools, this festive event serves as one of the biggest celebrations in downtown Pensacola. The Pensacola Runners Association has also collaborated with the Cox Pensacola Christmas Parade for the annual Downtown Parade Christmas Dash. This 1.2 mile-race will be held just before the parade and will run along the same route. The Blue Angels flight demonstration crew will also make a special appearance during the parade. For more information, visit

Gulf Breeze Zoo Christmas ZOObilee

December 9, 10, 16 & 17

Gulf Breeze Zoo will host the fifth annual Christmas ZOObilee on select weekends throughout the month of December. Featuring live music and entertainment, winter-themed bouncy houses, tasty holiday treats and special gifts from local artists in the Candy Cane Market, there will be something for the entire family to enjoy. There will also be a visit from Santa Claus himself and Whoville’s very own, Mr. Grinch. A chili cook-off will also be held from 11 am to 2 pm as part of this year’s festivities. A special dance party will take place at 1:30 pm to help those kiddos get those Christmas jitters out. Gulf Breeze Zoo will be open 10 am to 4 pm throughout the holiday season. For tickets and complete event details, visit

White Tie Rock Ensemble–A White Tie Christmas

December 16

The White Tie Rock Ensemble will present a holiday tribute concert featuring the music of the Trans-Siberian Orchestra, Paul McCartney, The Eagles, Bruce Springsteen and many other favorites at the Pensacola Bay Center on December 16 at 8 pm. The White Tie Christmas show combines the familiarity of classic rock with a symphonic orchestra to create a compelling new sound that audiences are sure to love. Tickets start at $20 and can be purchased online at

Jim Brickman: A Joyful Christmas

December 22

The Pensacola Saenger Theatre welcomes back Jim Brickman this holiday season with his new show, A Joyful Christmas, on December 22 at 7:30 pm. He will be joined with Emmy and Golden Globe nominee Chrissy Metz from the critically acclaimed NBC series, This is Us. The woman we see on the big screen can be seen on the big stage right here in Pensacola; Metz signed a record deal with Universal Music Group in Nashville, and has appeared in other hit TV shows like American Horror Story, Superstore, The Last OG, My Name is Earl and more. Join the duo for a magical evening of holiday carols, classics and Brickman’s top hits. For tickets and information, visit or

Celebrate the New Year! presented by Pensacola Symphony Orchestra

December 31

Pianist and vocalist, Tony DeSare, will bring his infectious cheer and powerful talents along with the Pensacola Symphony Orchestra to the Pensacola Saenger Theatre stage for a special New Year’s Eve performance at 7 pm. Featuring hits from Elton John, Ray Charles and Billy Joel, DeSare will bring you an evening of nostalgic classics and Broadway favorites from Wicked, Les Misérables, West Side Story and more. Visit for more information and to buy tickets.

New Years Fireworks at Pensacola Beach

December 31

Ring in the new year with the Pensacola Beach Chamber as they host a special fireworks show at Midnight on New Year’s Eve. Watch dazzling fireworks paint the sky as the clock strikes Midnight. Spectators are invited to watch the show from Pensacola Beach or Santa Rosa Sound. Close out 2023 with a bang at the New Years fireworks show on Pensacola Beach. For details, visit

Polar Bear Plunge at Pensacola Beach

January 1

Dip your toes into the icy cold water at the Pensacola Beach 2024 Polar Bear Plunge. Join hundreds of other dippers for this annual tradition as they ring in the new year. Dippers will meet at at 2 pm at the Paradise Bar & Grill and then, head off to take the plunge. There is a $15 cash registration fee, which includes a commemorative Polar Bear Plunge t-shirt. Kids, ages 10 and under, can participate for $5. Registration begins at noon. For more information and to register, visit