Season Guide to Must-See Performances on Florida's Cultural Coast®

The Sarasota Ballet opens its 20th season under the direction of Iain Webb, with an anniversary lineup of 16 ballets, including eight company premieres. The season's centerpiece, The Nutcracker, features the Sarasota Ballet Studio Company and more than 100 students from the company's education programs. The production returns to the Venice Performing Arts Center, Dec. 11-12, 2026, and to the historic Sarasota Opera House, Dec. 20-22, 2026.

Grab a bite: Next door to the Opera House, begin or end your evening at Rose & Ivy, serving steaks, sushi rolls and creative cocktails inside a charming, circa-1925 ivy-covered building. On a cool evening, take your drink out to the courtyard and cozy up by the heaters.

The iconic purple hall on Sarasota's bayfront kicks off its Broadway series with The Bodyguard, Nov. 30-Dec. 2, 2026, followed by favorites like Legally Blonde and Mamma Mia! The season closes with Alicia Keys' Hell's Kitchen, one of six Sarasota premieres this season, running April 13-18, 2027.

Grab a bite: For an easy pre-show meal, head to Sarasota's Bayfront Park, just minutes away, to the marina-side restaurant Marina Jack. Choose from fine dining indoors, a lively outdoor patio overlooking the boats moored in Sarasota Bay or an intimate piano bar with nightly live music. 

Located on the grounds of The Ringling, this elegant 18th-century jewel-box theater was originally built in Italy, then dismantled and reassembled in Sarasota. Asolo Rep's 2026-27 season, themed "The Greatest Season on Earth," marks the 100th anniversary of the circus's move to Sarasota. It opens on the Mertz stage with the movie-musical favorite Singin' in the Rain, Nov. 18, 2026-Jan. 2, 2027, and closes with Baskerville: A Sherlock Holmes Mystery, on May 5-30, 2027.

Grab a bite: Depending on whether you catch a matinee or an evening show, walk across the grounds to The Ringling Grillroom, a modern American restaurant on the ground floor of the McKay Visitor's Pavilion overlooking the Ringling estate.

Located in the artsy Rosemary District, Westcoast Black Theatre Troupe (WBTT) is the only professional Black theater company on Florida's west coast and is known for original, high-energy productions. WBTT opens its 27th anniversary season, themed "Rhapsodies of Rhythm," with the Tony Award-winning musical revue Sophisticated Ladies, a tribute to Duke Ellington, Oct. 14-Nov. 22, 2026, followed later in the season by the company's first-ever Shakespeare production, A Midsummer Night's Dream, Jan. 13-Feb. 21, 2027.

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

In Historic Downtown Venice, the Raymond Center is home to the nationally acclaimed Venice Theatre, one of the largest, most active in the United States. Now in its 77th season, theatergoers can catch the popular Disney musical Freaky Friday, running Oct. 30-Nov. 22, 2026.

Grab a bite: Before or after the show, stroll across the street to Café Venice Restaurant & Bar, an intimate, bistro-style landmark locals love. Share a bottle of fine wine and a few European-inspired tapas.

As the oldest continuously operating orchestra in the state of Florida, Sarasota Orchestra opens its season, "It's Better Live," under Music Director Giancarlo Guerrero, with the Masterworks opener Beethoven & Prokofiev, featuring violinist Gil Shaham, Nov. 7-8, 2026, and closes the series with Chopin & Mahler, featuring pianist Emanuel Ax, April 3-4, 2027.

Grab a bite: Across the main road from Holley Hall, head inside the trendy Sarasota Modern Hotel for drinks at Wink Wink Food & Drink, a restaurant and lounge inspired by retro supper clubs and breezy tiki bars, with a modern twist.

At the Venice Performing Arts Center, The Venice Symphony opens its season, "See Where Music Takes You," under Music Director Troy Quinn. Music lovers can catch A Ghoulish Gathering on Oct. 9-10, 2026 for an symphonic exploration of the mysterious and supernatural.

Grab a bite: Before heading to VPAC, catch the sunset at Crow's Nest Marina Restaurant on Venice's waterfront, known for its fresh-caught seafood, steaks and chops.

The main Sarasota Opera season takes place during the winter months, running an intensive Winter Opera Festival from February through March each year. The 69th season will see a handful of performances, including La traviata by Giuseppe Verdi and Ariadne auf Naxos by Richard Strauss, but will kickoff with the fall production of Hansel and Gretel, Oct. 30-Nov.14. 

Grab a bite: Just around the bend from Downtown Sarasota's Opera House is the boutique Art Ovation Hotel. Inside the lobby, visitors and locals can dine at its elegant Mediterranean restaurant, Tzeva. Enjoy tapas and cocktails, then walk over to catch the opera for a memorable evening.

Florida Studio Theatre offers intimate and engaging performances across five venues in the heart of Downtown Sarasota. The historic theatre's winter mainstage season opens with the Tony Award-winning musical Kimberly Akimbo, Nov. 18, 2026-Jan. 3, 2027, and closes with the regional premiere of How the Light Gets In, April 7-May 3, 2027.

Grab a bite: Directly across the street, stop into Sage SRQ for an international fine dining menu, craft cocktails, exquisite desserts and one of downtown's best rooftop views.

Downtown Sarasota's Urbanite Theatre, an intimate black-box venue known for its daring and contemporary productions, opens its 13th season with Ahoy-Hoy, Oct. 30-Nov. 29, 2026, and closes with Black Bastard, a solo show by Jon Gentry, June 4-27, 2027.

Grab a bite: Just a block away off of Main Street, Bevardi's Salute! serves authentic Italian fare with house-made pasta and open-air sidewalk seating to enjoy cool Florida nights. Settle under the hanging lights on the terrace for a glass of wine to people-watch before or after the show.

The Pops Orchestra opens its 51st season, "Like No Other," with Hocus Pocus Pops II, Oct. 30, followed by Born in the U.S.A., a tribute to Bruce Springsteen, Nov. 14-16, 2026. The season continues throughout the winter with spellbinding tributes and collaborations, and closes with How Low Can You Go?, April 11-12, 2027, perfect for those who love groovy, bass-heavy tunes. 

Grab a bite: The company primarily performs at Riverview Performing Arts Center in Sarasota or Neel Performing Arts Center in Bradenton. Whichever venue you end up, there is likely a Gecko's Grill & Pub location around. The beloved local chain serves up award-winning American pub food with a gourmet twist, plus a full bar and happy hour specials.

The Conservatory’s marquee collaboration, "Cirque des Voix," pairs circus artists with the 100-plus voice ensemble of Sarasota's Key Chorale and the musicians of The Venice Symphony under the Circus Sarasota Big Top at Nathan Benderson Park, Jan. 29-31, 2027.

Grab a bite: A short distance from the park at University Town Center, Selva Grill UTC serves beautifully plated, Peruvian-inspired dishes and creative cocktails. Also nearby is Fleming's Prime Steakhouse & Wine Bar, pairing USDA Prime steaks and an extensive wine list with nightly live music.

The region's oldest performing arts organization, founded in 1929, presents the gothic horror thriller Dracula, Oct. 3-25, 2026 as the start of its 97th season. Showings will temporarily take place at The Crossings at Siesta Key while the company prepares to move into its newly renovated home at Payne Park Auditorium in Downtown Payne Park. 

Come 2027, the season's productions continues, with plans to take place in its new performance venue. Expect the Broadway-hit musical, The Producers, Jan.7-24 and Oscar Wilde's famous comedy,The Importance of Being Earnest, Feb. 6-28.

Grab a bite: If you plan to catch October's production, grab a table at New American fusion eatery, Baker & Wife, across the street from The Crossings retail center. Once The Sarasota Players moves downtown, there are a myriad of dining options available. Ticket holders can make reservations for an elevated bite to eat and craft cocktails at nearby State Street Eating House + Cocktails or Boca Sarasota.

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!

Grab a bite: Right on Sarasota Bayfront near many downtown venues, O'Leary's Tiki Bar & Grill serves tropical drinks, casual bites and live music under a waterfront tiki hut.