Sarasota’s Cultural Gems: Our TOP 28 Picks for the 2019/20 Season

While there is an abundance of Art, Music, and Educational Events in Sarasota throughout the year, the “Season” is like a Tsunami of cultural content. There are special exhibits at our local living museums, continuing education and distinguished speakers at our five colleges & universities, festivals & street fairs, and finally the local venues are stacked with performances and talks. The list is practically endless with more opportunities than you can physically attend and at almost every budget.

Since not everything is listed in one place, finding all of the things to do is a bit of a challenge. This year we have gone through the events and have curated a list of old favorites, new things, and a few undiscovered gems.

As I was curating this list, my kids were looking over my shoulder and commenting on all the things that they want to do. So if you have an extra ticket and want a teenager or two we are happy to send them along with you. 😃


Here are the top picks in chronological order:

The Thanksgiving Play by Larissa FastHorse

When: November 8 to December 15

Where: Urbanite Theatre Downtown Sarasota

Is it possible for a troupe of all-white teaching artists to create a culturally sensitive pageant to celebrate Native American Heritage Month? Subversive, absurd and endearing, The Thanksgiving Play is a blistering satire that hilariously dissects political correctness, just in time for the holidays.

Chalk Festival

When: November 15-18

Where: Venice Airport, Venice Island

See hundreds of pavement artists turning the road surface into a “museum in motion” using chalk as their medium.

Siesta Key Crystal Classic

When: November 15-18

Where: Siesta Key Beach

International Sandsculpting Festival

Brundibár by the Children’s Youth Opera

When: November 15-16

Where: Sarasota Opera House

Love Conquers Evil. Performed at least 55 times by the children of Theresienstadt concentration camp during WWII, this tale of friendship, perseverance, and teamwork will touch your heart.

Ain’t No Stoppin’ Us Now!

When: November 18

Where: Van Wezel

This high-energy celebration marking 20 years of soul on stage features original Westcoast Black Theatre Troupe members, including Founder/Artistic Director Nate Jacobs, and many other audience favorites. Highlights will include songs from WBTT’s most memorable musicals, including original compositions, Broadway tunes spanning the decades and Motown hits — backed by the live WBTT house band. Special appearance by RCA record…

Shawn Wayans

When: November 22 and 23

Where: McCurdys Comedy Theatre

Shawn made his acting debut in 1989 in his brother Keenen Ivory Wayans’ feature film “I’m Gonna Get You Sucka.”

Immediately following his feature film debut, Shawn joined the cast of the Emmy Award-winning comedy series, “In Living Color.”

Shawn starred in the box office hits, “Little Man,” “White Chicks,” “Scary Movie,” “Scary Movie 2,” just to name a few!
“The Wayans Bros.” sitcom, which Shawn and Marlon created and starred in, was the first WB show to be sold into syndication after heading up the WB network lineup for five years.

Assisted Living the Musical

When:November 29 to December 22

Where: Venice Little Theater

The comedy team of Compton and Bennett are off their walkers again in this hysterical sequel to the runaway hit about the nursing home and beyond. Christmas, Hanukkah, and retirement will never be the same.

Tony Bennett: The “I Left My Heart” Tour

When:December 3

Where: VanWezel

Tony Bennett’s career as the pre-eminent singer of the 20th and 21st centuries is unprecedented. He has received 19 Grammy Awards® including the Grammy Lifetime Achievement Award, 2 Emmy Awards® and is a Kennedy Center Honoree and NEA Jazz Master. Bennett is one of a handful of artists to have new albums charting in the ’50s, ’60s, ’70s, ’80s, ’90s, and now in the first two decades of the 21…

Motown Christmas performed by WestCoast Black Theater Troupe

When:December 4-6 and December 18-20

Where: Sarasota Opera House

Celebrate the season with this festive holiday revue. It’s the perfect blend of traditional Christmas carols paired with soulful songs made famous by such Motown celebrities as Marvin Gaye, Stevie Wonder, the Supremes and The Jackson 5. WBTT’s sizzling signature style makes this a most memorable Christmas treat that’s fun for the whole family!

Handle with Care

When:December 11 through March 8

Where: Florida Studio Theater

A young woman from Israel, Ayelet, reluctantly joins her grandmother on a trip to the United States. Circumstances both absurd and tragic bring Ayelet, who has little command of the English language, together with Josh, a young American man who has little command of romance, on Christmas Eve. Is their inevitable love an accident…or is it destiny, generations in the making?


When:December 12

Where: Sarasota Opera House

PINC is People, Ideas, Nature, and Creativity. It’s a one-day, conference-style experience delivered by a cascade of international speakers from every imaginable discipline, skill, and talent you can think of, and many of you had no clue it even existed. Speakers range from Iditarod champions, the founder of Vertical Farming, a famous felt artist and a lawyer whose territory is outer space, all the way to Nobel Prize winners, perfume virtuosos, a Master Acoustician, and the doctor who performed the first hand transplant.

Whether a speaker or a guest, the PINC experience attracts creative thinkers, entrepreneurs, specialists, designers, artists, scientists, and any one looking to stimulate their mind, heart, and soul. It’s an opportunity to participate in an eclectic mix of the fundamental pieces that create the human experience.

Bugs Bunny at the Symphony by Sarasota Orchestra

When:January 3-4

Where: Van Wezel

This popular concert has been touring the world with sold-out performances for three decades, and now returns to Sarasota Orchestra in a newly-revised 30th Anniversary Edition. This critically-acclaimed production projects the world’s most iconic Looney Tunes on the big screen, while the orchestra plays the classically-infused original scores live! From “What’s Opera, Doc?” and “The Rabbit of Seville,” to “Baton Bunny,” “Corny Concerto,” “Rhapsody Rabbit,” and “Long-Haired Hare,” don’t miss the brilliant cartoons that first introduced classical music to much of the American public. Plus five brand new animated shorts, newly-created by the Warner Bros. animators in celebration of Bugs Bunny’s 80th Birthday in 2020.

American Son

When:January 22 through March 22

Where: Florida Studio Theater

Set in a Miami-Dade police station in the middle of the night, a mother is hunting for answers about her missing teenage son. Soon her husband appears, and the evening spirals out of control. Fresh from its critically-acclaimed Broadway run, this powerful drama tackles family relationships, love, loss, and identity.

The Lifespan of a FACT

When:January 22 to March 19

Where: Asolo Reperatory

How negotiable is a fact? That’s the premise of this critically acclaimed 2018 Broadway hit filled with blistering comedy and contemporary relevance. At a high-end magazine, a demanding editor-in-chief hires a determined millennial fact-checker to work on a groundbreaking essay written by a famous author. Like magazines everywhere, this one is reeling from poor ad sales and shrinking circulation. But with this potentially sensational essay, salvation looms. The deadline is tight, the essay is dense, and everyone must make a good faith effort to tell the story honestly. When the fact checker goes too far, the ultimate showdown between “truth” and “accuracy” begins – with delicious consequences.

Steve Martin and Martin Short

When:January 23

Where: Van Wezel

This duo returns to the Van Wezel by popular demand! Their celebrated comedy show, The Funniest Show in Town at the Moment: Steve Martin & Martin Short, featuring The First Ladies of Bluegrass redefines the form in unexpected and profound ways, from two of the funniest, most influential and acclaimed talents of the past century.

Steve Martin and Martin Short’s recent sold-out tour, An Evening You Will Forget for the Rest of Your Life, was filmed for a Netflix special that garnered four Emmy® nominations. Rolling Stone called the special “wryly hip but unexpectedly touching,” with The New York Times describing it “gleeful and satisfying.”

General John Kelley

When:January 27

Where: Van Wezel

Ringling College Library Association Speaker Series

After less than a year in retirement Secretary Kelly was offered the opportunity to serve the nation and its people again, now as the Secretary of Homeland Security. After he and his family served a lifetime in service to the nation—and knowing no other life—the opportunity to serve again was welcomed. The U.S. Senate gave him and his family the great honor of confirming him on January 20, 2017 and he was immediately sworn in as the fifth Secretary of Homeland Security. After six months, he was selected to serve as White House Chief of Staff, a position he held until January 2019.

La bohème

When:February 8-March 21 (select dates)

Where: Sarasota Opera House

Love Is Fragile. Almost two centuries ago in Paris’ Latin Quarter, a love affair flourishes, withers and dies in Puccini’s romantic portrayal of bohemian life. This has particular meaning to us as we spent the year in Puccini’s hometown of Lucca when our children were in 3rd and 5th grade. We were surrounded by Opera. Put an Italian in Paris and voila!

The Beach Boys

When:February 18

Where: Van Wezel

The Beach Boys return to the Van Wezel! The legendary band is led by Mike Love and Bruce Johnston, who, along with Tim Bonhomme, John Cowsill, Keith Hubacher, Christian Love, Brian Eichenberger, Randy Leago and Scott Totten continue the group’s legacy.

The Beach Boys have birthed a torrent of hit singles and sold albums by the tens of millions. Their songs have forever changed the musical landscape, profoundly influencing countless performing artists to follow. Don’t miss your favorite hits including “Surfin’,” “Fun, Fun, Fun,” “I Get Around,” “Help Me Rhonda,” “California Girls,” “Good Vibrations” and “Kokomo.”

The Art of Art Recovery: Recovering Stolen and Looted Works of Art

When:February 20

Where: New College of Florida

Featuring Christopher A. Marinello, Esq. ’83, CEO, Art Recovery International

Christopher A. Marinello is one of the world’s foremost experts in recovering stolen and looted works of art. A practicing lawyer for over 34 years, Chris began his career as a litigator and became uniquely proficient in negotiating complex title disputes on behalf of collectors, dealers, museums, and insurance companies.

Chris will provide an overview on art crime and the legal issues involved in recovering stolen and Nazi-looted works of art. He will present numerous case studies involving some high-profile recoveries and give the audience an opportunity to ask questions about this unusual profession.


When:February 28 to March 1

Where: FSU Center for the Performing Arts (Sarasota)

The Sarasota Ballet Presents the Paul Taylor Dance Company

The Great Leap

When:Begins March 18

Where: Asolo Reperatory Theater

San Francisco, spring 1989. Manford Lum is a sparky kid who plays street basketball in Chinatown – vertically challenged, but with undeniable ball skills. He talks his way onto a college team headed to Beijing for an exhibition game and finds himself in the middle of China’s post-Cultural Revolution. As the story bounces between 1989 and 1971, past relationships collide with present day revelations right up to the final buzzer. Smart, feisty and hilarious, The Great Leap is about family, history, and learning that every game is a second chance.

Itzhak Perlman in Recital

When: March 21

Where: Van Wezel

Undeniably the reigning virtuoso of the violin, Itzhak Perlman enjoys superstar status rarely afforded a classical musician. Beloved for his charm and humanity as well as his talent, he is treasured by audiences throughout the world who respond not only to his remarkable artistry, but also to his irrepressible joy for making music.

Itzhak Perlman’s recordings have garnered 16 GRAMMY® Awards and regularly appear on the best-seller charts. In 2008, Mr. Perlman was honored with a Grammy Lifetime Achievement Award for excellence in the recording arts.

Annie Leibovitz

When: April 7 2020

Where: Van Wezel

Ringling College Library Association Speaker Series

Annie Leibovitz began her career as a photojournalist for Rolling Stone in 1970, while she was still a student at the San Francisco Art Institute. Her pictures have appeared regularly on magazine covers ever since. Leibovitz’s large and distinguished body of work encompasses some of the most well- known portraits of our time.

Reza – Edge of Illusion

When: April 11

Where: Van Wezel

Reza has taken the art of illusion to a new level, delivering his rock concert style magic show to audiences across the globe. Young and fresh, Reza’s new show, “Edge of Illusion,” has earned various awards including “Magician of the Year.” Don’t miss this Sarasota premiere – LIVE on the Van Wezel stage!

Suessical the Musical

When: April 16-19

Where: Booker Visual and Performing Arts High School

The Cat in the Hat tells the story of Horton, an elephant who discovers a speck of dust that contains the Whos, including Jojo, a Who child sent off to military school for thinking too many “thinks.” Horton faces a double challenge: not only must he protect the Whos from a world of naysayers and dangers, but he must guard an abandoned egg, left in his care by the irresponsible Mayzie La Bird. Although Horton faces ridicule, danger, kidnapping and a trial, the intrepid Gertrude McFuzz never loses faith in him. Ultimately, the powers of friendship, loyalty, family and community are challenged and emerge triumphant.

American Playlist by Sarasota Orchestra (POPS)

When: April 17-18

Where: Van Wezel

Chanteuse Storm Large (from the popular group Pink Martini) and NEA Jazz Master and musical icon Branford Marsalis, a saxophonist who has garnered legendary status, join forces for an electrifying Pops extravaganza that will have audiences swaying in their seats. Enjoy everlasting classics such as I’ve Got You Under My Skin, Goin’ Out of My Head, It’s Alright with Me, Summertime, My Funny Valentine and more!


When: April 28-May 3

Where: Van Wezel

Broadway’s COME FROM AWAY is a Best Musical winner all across North America! This New York Times Critics’ Pick takes you into the heart of the remarkable true story of 7,000 stranded passengers and the small town in Newfoundland that welcomed them. Cultures clashed and nerves ran high, but uneasiness turned into trust, music soared into the night, and gratitude grew into enduring friendships.

On 9/11, the world stopped.

On 9/12, their stories moved us all.

Don’t miss this breathtaking new musical written by Tony® nominees Irene Sankoff and David Hein, and helmed by this year’s Tony-winning Best Director, Christopher Ashley. Newsweek cheers, “It takes you to a place you never want to leave!”

Outdoor POPS by Sarasota Orchestra

When: May 8-9

Where: Ed Smith Stadium

Join Sarasota Orchestra for a fan-friendly outdoor Pops concert at the Orioles’ Ed Smith Stadium. This seventh annual concert showcases stirring music, big vocals, and popular music. Get yourself some ballpark fare, sit back in the stands and enjoy the Orchestra performing from the field. A spectacular fireworks display closes out an evening of hits and home runs.

See you around town!

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