The best things to do in Sarasota, Lakewood Ranch, Longboat for May 28-June 3

Don't miss these arts and entertainment events around Sarasota and Manatee counties this week.


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  • | 12:01 p.m. May 26, 2026
Hermitage Fellow and Grammy Award winner Rona Siddiqui teams up with Westcoast Black Theatre Troupe performers Raleigh Moseley II and Maicy Powell for Hermitage Sunset Music on the Beach on Thursday, May 28.
Hermitage Fellow and Grammy Award winner Rona Siddiqui teams up with Westcoast Black Theatre Troupe performers Raleigh Moseley II and Maicy Powell for Hermitage Sunset Music on the Beach on Thursday, May 28.
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Thursday, May 28

Sunset Music on the Beach
6:30 p.m. at Hermitage Artist Retreat, 6630 Manasota Key Road, Englewood
$5 with registration
Visit HermitageArtistRetreat.org.

Hermitage Fellow Rona Siddiqui, a Grammy-nominated musical theater composer, shares the stage with local performers Raleigh Moseley II and Maicy Powell of Westcoast Black Theatre Troupe. Siddiqui will discuss her approach to songwriting and Moseley and Powell will perform as the sun sets on this beachfront performance. This is one of those sublime experiences sure to spark the sentiment, “This is why we live here.” Bring your own refreshments. 


‘Honky Tonk Angels’
7 p.m. at Florida Studio Theatre’s Gompertz Theatre, 1265 First St.
$25-$59
Visit FloridaStudioTheatre.org.

Join three Dolly Parton wannabes on a road trip to Nashville as they follow their dreams of country music stardom. This musical journey gives its stars the chance to belt out country favorites like Parton’s “9 to 5” and Tammy Wynette’s “Stand By Your Man.” Runs through June 21. 


Collin Purcell, Katie Blackwell and Brian Ott star in Florida Studio Theatre's cabaret,
Collin Purcell, Katie Blackwell and Brian Ott star in Florida Studio Theatre's cabaret, "Leaving on a Jet Plane."
Photo by Sorcha Augustine


‘Leaving on a Jet Plane’
7 p.m. at Florida Studio Theatre’s Goldstein Cabaret, 1239 N. Palm Ave.
$42
Visit FloridaStudioTheatre.org.

Created by Aaron Gundy, “Leaving on a Jet Plane” features an acoustic trio of talented performers who will take you on a flight to the feel-good era of folk music in the late 1960s and 1970s. Among the singer/songwriters whose works are featured in this upbeat show are Simon & Garfunkel, Cat Stevens, Crosby, Stills & Nash and the Lovin’ Spoonful. 


Alexis J. Roston (left) stars as Marie Knight, the new performing partner of Sister Rosetta Tharpe (Maiesha McQueen), in Asolo Repertory Theatre's new play,
Alexis J. Roston (left) stars as Marie Knight, the new performing partner of Sister Rosetta Tharpe (Maiesha McQueen), in Asolo Repertory Theatre's new play, "Marie and Rosetta."
Photo by Adrian Van Stee


‘Marie and Rosetta’
7:30 p.m. at FSU Center for the Performing Arts, 5555 N. Tamiami Trail
$65-$71
Visit AsoloRep.org.

Students of popular music know that Sister Rosetta Tharpe earned the nickname “the godmother of rock ‘n’ roll” for transforming gospel music with her fierce guitar playing. Asolo Repertory Theatre’s latest production captures the first rehearsal between Tharpe (Maiesha McQueen) and one of her acolytes, Marie Knight (Alexis J. Roston), as they prepare for a world tour. Runs through May 31. 


Friday, May 29

Diversity: The Voices of Sarasota Pride Month Kick-Off Concert
7 p.m. at First Congregational UCC, 1031 S. Euclid Ave.
Free
Visit DiversitySarasota.org.

The Diversity: The Voices of Sarasota choir presents this free Pride Month kick-off concert at First Congregational UCC Sarasota, featuring songs centered on hope and inclusion. Donations will be accepted at the door.


‘One Hit Wonders’
9 p.m. at Florida Studio Theatre’s John C. Court Cabaret, 1265 First St.
$37-$42
Visit FloridaStudioTheatre.org.

Is it better to have had just one song top the charts than to have none at all? You’ll have time to think about that question as you listen to such hit songs as Don McLean’s “American Pie,” a runaway hit that eclipsed other success in the troubadour’s career, and “Don’t Worry, Be Happy” from Bobby McFerrin. Created by Richard and Rebecca Hopkins, “One Hit Wonders” is directed by FST Associate Producer Catherine Randazzo with arrangements by Jim Prosser. Runs through June 21. 


Saturday, May 30

Schmidt Vocal Arts National Competition
9:45 a.m. at Sarasota Opera House, 61 N. Pineapple Ave.
$15.45, students $10
Visit SarasotaOpera.org

High-school students  from around the country compete for up to 16 places in the final round of the Schmidt Vocal Arts National Competition. A total of 58 teen singers have advanced to the semifinals, presented in partnership with the Sarasota Opera. Cash prizes of up to $10,000 will be awarded and three semi-finalists will be selected to participate in a master class before the final round. Continues May 31.


An interior view of a mobile juxtaposed with botanical creations at Marie Selby Botanical Gardens.
An interior view of a mobile juxtaposed with botanical creations at Marie Selby Botanical Gardens.
Photo by Marty Fugate


Alexander Calder: The Nature of Movement
10 a.m. at Marie Selby Botanical Gardens, 1534 Mound St.
$28
Visit Selby.org.

It’s last call for Marie Selby Botanical Gardens’ tribute to Alexander Calder and his abstract moving sculptures, dubbed “mobiles.” Calder’s interest in suspension provides a provocative pairing with Selby’s collection of epiphytes, or air plants in Selby’s annual Jean & Alfred Goldstein Exhibition. Runs through May 31. 


‘Blockbusted’
7:30 p.m. at FST’s Bowne’s Lab, 1265 First St.
$15-$18
Visit FloridaStudioTheatre.org.

What’s the best entertainment bargain in town? No, it’s not a movie ticket ($15.99 at the Regal Hollywood 11) nor Netflix ($19.99 a month for standard service). It’s the Saturday night performances of Florida Studio Theatre Improv, which top out at $18 a ticket. You’ll laugh so hard you'll cry at these ever-changing lineups. “Blockbusted” takes audiences back to the days of the video store as fearless improvisers face off against each in sketches powered by audience suggestions. It’s the perfect date night for young and old. 


Sunday, May 31

‘Something Borrowed, Something New’
11 a.m. at the Sarasota Art Museum campus of Ringling College, 1001 S. Tamiami Trail
$20
Visit SarasotaArtMuseum.org.

 “Something Borrowed, Something New”  features major modern artists such as Louise Bourgeois, Chuck Close, David Hockney, Yoko Ono, Kara Walker and Ai Weiwei. Their works have been loaned by private collectors in Southwest Florida to SAM for the show, which runs from April 19 through Sept. 27.


Sundays at The Bay featuring Tasa + Rob
6 p.m. at The Oval, 1055 Boulevard of the Arts
Free with registration
Visit TheBaySarasota.org.

This concert series features a different local performer each week. This week's featured artist is Tasa + Rob, who perform unique renditions of cover tunes from a wide range of genres, using voice, guitar, violin and cajun. Registration requested.


Monday, June 1

Savor Sarasota Restaurant Week
Eateries in downtown Sarasota, St. Armands Circle, Lakewood Ranch, Siesta Key and Venice
$25 for lunch and $45 for dinner
Visit VisitSarasota.com.

Now in its 21st year, Savor Sarasota Restaurant Week is actually a two-week period where more than 50 restaurants offer prix fixe menus that give locals the chance to step out of their comfort zone and try new dishes for affordable prices. Lunch menus are just $25 per person and dinner offerings are just for $45 during what many locals call “the most wonderful time of year.” 


Ancient Art from Cyprus and the Mediterranean
10 a.m. at The John and Mable Ringling Art Museum, 5401 Bay Shore Road
Free with $30 admission; Mondays free
Visit Ringling.org.

In 1928, circus magnate John Ringling moved beyond collecting Baroque paintings with a major acquisition of more than 2,000 pieces of Cypriot art at the Anderson Galleries in New York, where the Metropolitan Museum was selling parts of its ancient art collection. For the first time, Ringling's treasures have a permanent home in Gallery 12 after a decadelong project.


Tuesday, June 2

"It's Alive! Live!" is one of nine shows featured in the Squeaky Wheel Fringe Festival, which runs June 2-7 at the Cook Theatre in the FSU Center for Performing Arts.
Courtesy image

Squeaky Wheel Fringe Festival Teaser Show
7 p.m. at Cook Theatre, FSU Center for the Performing Arts, 5555 N. Tamiami Trail
Pay what you will
Visit SqueakyWheelTheatre.org.

Not sure what a fringe festival is or if it’s for you? Here’s a way to find out what the fourth annual Squeaky Wheel Fringe Festival is all about. This pay-what-you-will teaser show is a showcase of the nine shows in the festival, which runs through June 7. Squeaky Wheel Fringe Festival founder Megan Radish describes her baby as a “smorgasbord” of performances that are uncensored. And it’s not one type of performance. It can be drama, dance, comedy, music or all of the above.


Wednesday, June 3

Levin Lecture
4 p.m. at Holley Hall, 709 N. Tamiami Trail
$15-$25
Visit SarasotaOrchestra.org

This year’s Sarasota Music Festival is a slimmed-down affair following the departure of longtime artistic director Jeffrey Kahane in 2025. But some things won’t change, namely the annual lecture by Kahane’s predecessor, Robert D. Levin. The pianist, composer and conductor was head of the Sarasota Music Festival for a decade and is a former professor of music at Harvard University. Levin is an expert on improvisation in classical music, and this lecture is sure to include musical interludes. 



Squeaky Wheel Fringe Festival: ‘Casa Havana’
7 p.m. at Cook Theatre, FSU Center for the Performing Arts, 5555 N. Tamiami Trail
$20.70
Visit SqueakyWheelTheatre.org.

Tania Vergara, founder and artistic director of Endedans Contemporary Ballet, presents "Casa Havana." Set in modern-day Cuba, the piece tells the story of three siblings and their mother. The mother is anguished by her fear of the government and worries that her children could be punished for making their views known. But it is a son who chooses to leave that is the source of true heartbreak.

 

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