Holiday Curtain Call: Must-See Performances This Season

Experience the timeless magic of Tchaikovsky’s beloved ballet and a holiday favorite at Downtown Sarasota's historic Sarasota Opera House—celebrating its 100th year in 2026! 

The Nutcracker comes to life with lavish sets, glittering costumes and graceful choreography by The Sarasota Ballet Studio Company. Leave the outside world behind for an unforgettable story of music and dance following Clara and her Christmas adventure. There will be four showings December 21-23, 2025. Don't miss this magical performance! 

Grab a bite: Next door to the Opera House, begin or end your evening at Rose & Ivy restaurant. Enjoy steaks, sushi rolls and creative cocktails in a charming, circa-1925 ivy-covered building. If the evening is cool and breezy, wander to the outdoor garden courtyard with your drink and cozy up by the heaters.

Venture to the iconic purple building of Van Wezel Performing Arts Hall to grab one of the 1,741 seats within its Roskamp Auditorium. This season, the Van Wezel pulls out all the stops with an expanded holiday lineup that delivers Broadway flair, magical cirque and classic tales that delight every age:

Cirque Musica Holiday Wonderland (Dec. 21, 2025) – A breathtaking fusion of acrobatics, aerial arts and holiday melodies that turns the auditorium into a winter spectacle of circus wonder. 
A Very Broadway Christmas (Dec. 22, 2025) – Sing along to festive favorites from shows like Phantom of the Opera, Wicked, Book of Mormon and Annie, performed by Broadway stars with live band and dazzling dance numbers. 
A Christmas Carol (Dec. 23, 2025) – Charles Dickens’ timeless classic comes alive in a new adaptation filled with puppetry, rich costumes and beloved carols—perfect for a heartwarming family evening. 

Grab a bite: For a magical evening, cruise over to Sarasota's Bayfront Park (just a few minutes' drive) to the marina-side restaurant, Marina Jack. Featuring multiple restaurant concepts in one spot, choose from fine dining inside, a lively outdoor patio or an intimate piano bar lounge with live music nightly. 

Located on the grounds of The Ringling Museum, discover one of Sarasota's finest gems. This elegant, 18th-century jewel-box theater was originally built in Italy, then dismantled and reassembled here in Sarasota. 

Asolo Rep's programming presents the return of its sell-out run of All Is Calm: The Christmas Truce of 1914, running Dec. 3-19, 2025. Following a German solider of The Great War, step back in time for this stirring story of hope, humanity and holiday peace told through song and story from the unsung heroes who lived it.

Grab a bite: Depending on whether you attend a matinee or an evening show, walk across the way to The Ringling Grillroom for lunch or dinner to enjoy the museum's Modern American restaurant, located on the ground floor of the McKay Visitor's Pavilion and overlooking the grounds of the beautiful Ringling estate.

Located in the artsy neighborhood of the Rosemary District, the Westcoast Black Theatre Troupe of Florida (WBTT) is the only professional black theater company on Florida's west coast. WBTT has received numerous awards and gained a reputation for original and sizzling performances—including its annual rendition of Black Nativity, adapted anew every time it's staged.

This vibrant, gospel-infused retelling of the Nativity story radiates energy, soul with gospel, blues, spiritual and Christmas music, paired with the poetry of Langston Hughes and the creativity of WBTT's cast. All ages will enjoy this high-energy, inspiring show, which runs November 20 – December 21, 2025.

Grab a bite: Just a few minutes' drive through Rosemary, discover the beautiful indoor-outdoor Arts & Central Restaurant for an after-show dinner and drink. Cozy up by the heaters and giant firepit on a cool night on its front patio with martinis, or head inside for an art-inspired menu of innovative shareable dishes.

In Historic Downtown Venice, make your way to the Raymond Center to witness the local talents of nationally acclaimed Venice Theatre. Celebrating its 25th-anniversary production, catch the theater's annual musical version of A Christmas Carol to celebrate the holidays.

Travel to Victorian London for the beloved adaptation of Charles Dickens’ classic story and meet Ebenezer Scrooge as he reflects on his past, present and possible future. The musical includes the original book and lyrics, plus additional music and new cast members, and runs Dec. 4-21, 2025.

Grab a bite: Before or after the show, carve out some time to stroll across the street to Cafe Venice Restaurant & Bar, an intimate, bistro-style landmark loved by locals. Share a bottle of wine from its extensive wine list and pair it with a few European-inspired tapas and desserts.

Have a holly jolly time catching the Sarasota Orchestra at Holley Hall. Set to put on a rousing symphony of seasonal favorites, the orchestra will fill the concert hall with a lineup of beloved carols in its Great Escapes concert series, Oh, What Fun! 

Highlights include Festive Sounds of Hanukkah and a local twist on The Twelve Days of Christmas, as well as selections from The Nutcracker, It's a Wonderful Life and The Polar Express. The Great Escapes series runs from Dec. 10-14, 2025. 

Grab a bite: Across the main road, make your way inside the trendy Sarasota Modern Hotel to grab after-party drinks at Wink Wink Food & Drink restaurant and lounge—inspired by retro supper clubs and breezy Tiki bars, but with a fun, modern twist.

At the beautiful Venice Performing Arts Center (VPAC), gift yourself and a loved one tickets to see The Venice Symphony in all its glory. The concert season includes a mix of masterworks, modern classics and popular symphonic music, and in December, make plans to hear the symphony's coveted Sounds of the Season, an annual celebration of music and togetherness. 

Become immersed in beloved Christmas carols and memorable seasonal tunes such as Good King Wenceslas, Rudolph the Red-Nosed Reindeer, Sleigh Ride and Mary Did You Know? The event includes special performances by a guest vocalist and Sarasota's Key Chorale. Catch three showtimes Dec. 19-21, 2025. 

Grab a bite: Before heading to VPAC, catch the sunset at Venice's waterfront at Crow's Nest Marina Restaurant—famous for its fresh-caught seafood, as well as choice steaks and chops. Dine upstairs in the elegant dining room for a lovely view of the marina or downstairs for a more casual tavern vibe.

In Englewood, make your way to Lemon Bay Playhouse, a community theater that produces seven plays every season. This year includes a dramedy called A Christmas Tail, a heartwarming story set in New York City of a mystical cat, a little girl and some holiday magic that occurs in a small butcher shop one Christmas Eve. Find multiple show times Dec. 3--21, 2025.

Grab a bite: Just a short drive away, find Farlow's on the Water to indulge in tropical cocktails and Caribbean flavors with a Southern twist. While others are hiding from the cold up north this time of year, make your spirits bright with a cool Florida breeze on the outdoor patio overlooking a scenic creek.

Back in Downtown Sarasota, head to Florida Studio Theatre (FST) for an intimate and engaging experience of improv comedy from local comedians and actors. This season, catch It's a Blundeful Life, an uproarious holiday romp—no script, no plan and no clue what’s coming next.

FST Improv spins a full-blown, improvised musical set in a Hallmark-style holiday tale each night with spontaneous song, drama, even choreography. Playing select nights November 29 – December 20, 2025, it’s a quirky, joyful twist on tradition you won’t want to miss.

Grab a bite: Directly across the street, stroll on over to fine-dining restaurant Sage SRQ. You can begin or end the evening here with an international culinary experience, some of the finest craft cocktails in the city and one of the best rooftop views of downtown to enjoy a Florida winter night in style.

Arriving just before the holiday season, Sarasota’s Living Arts Festival arrives each November and fills the city with cutting-edge performances, festive exhibitions and interactive art experiences—a perfect kickoff to a jam-packed performing arts winter on Florida’s Cultural Coast!