Fun Things to Do and See in Sarasota!
May 2025

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MARK YOUR CALENDAR

May 5 | Cinco de Mayo

May 11 | Mother’s Day

May 26 | Memorial Day

May 3

SUP & RUN 5K | Benderson Park

The 10th Annual SUP & RUN 5K at Nathan Benderson Park features three races, custom medals, standout race shirts, and a vibrant post-race celebration. Participants enjoy a beer garden, Sip & Rum station, and curated vendors. Races begin at 8 a.m.

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May 3

Derby & Dressage Dinner Party

Celebrate the elegance of equestrian sport and tradition at TerraNova Equestrian Center’s Derby and Dressage Dinner Party, featuring Olympic-level dressage and a live Kentucky Derby viewing.

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May 3

Corvettes on the Circle | St. Armand’s Circle

Held in St. Armands Circle Park, this Corvette show features over 150 classic and modern models. Trophies are awarded by generation, with proceeds benefiting Honor Flight of West Central Florida, supporting local veterans. A day of automotive excellence in support of a meaningful cause.

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May 3

4th Annual TacoFest | Manatee Fairgrounds

Manatee’s 4th Annual Taco Fest returns May 3, at the Manatee County Fairgrounds. Enjoy top food vendors, specialty cocktails, live entertainment, and family-friendly fun including a petting zoo, jump houses, and giveaways. Admission includes access to all entertainment and activities.

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May 3 & 4

Downtown Sarasota Craft Fair | 5 Points

Located in Sarasota’s 5 Points Park, this downtown art show features American handmade works—from fine jewelry to ceramics—ranging from $15 to $3,000. The weekend includes a vibrant Green Market offering exotic plants, gourmet goods, and artisan soaps, creating a lively blend of art, nature, and culture.

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May 4

Air Supply | Van Wezel

Graham Russell and Russell Hitchcock formed Air Supply in 1975, quickly rising to fame with a string of top-five hits rivaling The Beatles. With chart-topping singles and over 20 million albums sold, including Lost in Love and The One That You Love, Air Supply remains a beloved pop-rock duo.

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May 10

Dragon Boat Festival | Benderson Park

Open to ages 12 and up, this dragon boat event at Nathan Benderson Park features 200m, 500m, and 2K races. Community fun includes food trucks, a beer garden, entertainment, and a Health & Wellness Village. Free admission; $5 parking. Check-in starts at 6:30 a.m.

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May 11

Mother’s Day Brunch | Selby Gardens

Celebrate Mother’s Day with brunch at Selby Gardens, featuring a gourmet buffet by Michael’s on East, live music by The Vocalitas, and access to the gardens and George Harrison: A Gardener’s Life exhibition. Brunch includes stations, desserts, and drinks; additional beverages available for purchase.

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May 16 & 17

Spring Sidewalk Sale | Downtown Venice

Support small, local businesses during this two-day downtown sidewalk sale. Shoppers can enjoy exclusive deals, discover unique finds, and explore a variety of shops and boutiques. It’s the perfect opportunity to shop local, stroll the streets, and celebrate the community while taking advantage of limited-time savings and specials.

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May 17 & 18

Spring Fling Skim Jam | Nokomis Beach

The fifth annual Spring Fling Skim Jam returns to Nokomis Beach, one of Florida’s top Gulf Coast skim spots. This weekend event invites the skimboarding community to gather, compete, and showcase their skills in a vibrant, beachside setting known for its ideal conditions and enthusiastic local talent.

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May 21

Performances at the Point | Spanish Point

Enjoy an evening of acoustic folk-pop with Allie Sawicki at Selby Gardens' Historic Spanish Point campus. This Wednesday night series features live performances by local artists. Gates open at 6 p.m.; music begins at 6:30. Food and beverages available for purchase. Tickets are non-refundable and non-transferable.

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May 24

Memorial Day 5K | JD Hamel Park

SRQ VETS hosts the 10th Annual Memorial Day 5K Hike, uniting veterans and civilians to honor fallen heroes. The hike begins at JD Hamel Park, crosses the Ringling Bridge, and returns for a community cookout with music and inflatables. Proceeds support SRQ VETS' mission to aid local veterans.

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May 24

Venice Symphony Patriotic Pops

The annual Patriotic Pops Concert at CoolToday Park honors the 80th anniversary of WWII’s end with a tribute to the Greatest Generation. Enjoy Americana music by The Venice Symphony, guest vocalists, military salutes, and fireworks in a moving, multigenerational celebration of service and history in south Sarasota County.

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May 30

Venice Hurricane Expo

The City of Venice and the Venice Gondolier host the annual Hurricane Expo, offering expert talks on storm prep, emergency services, flooding, and post-hurricane recovery. Vendors provide resources, raffles, and giveaways, including weather radios. Food and drinks available. A vital community event ahead of hurricane season.

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LIVE

Local Theatre

Manatee Performing Arts Center

Running through May 11, Evita. Evita traces Eva Perón’s rise from poverty to power in 1930s–50s Argentina. The Tony-winning musical follows her transformation from actress to First Lady, capturing her political influence, public adoration and untimely death at 33. A story of ambition, charisma and legacy told through iconic music and riveting drama.

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Lemon Bay Playhouse

Running through May 11, The Puzzle with the Piazza. A septuagenarian faces a race against time to complete a long-unfinished 3,000-piece puzzle before leaving her home due to poor health. As she prepares to move in with her sister—without her puzzles—this poignant play explores family, friendship, and the connections that shape life’s final chapters.

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Florida Studio Theatre

Running through May 25, Jersey Boys. Experience the story of Frankie Valli and the Four Seasons, from their New Jersey beginnings to the Rock & Roll Hall of Fame. This electrifying show highlights their signature sound, rise to stardom, and personal struggles, offering an inside look at the journey that continues to captivate audiences worldwide.

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Van Wezel Performing Arts Hall

May 3, Fleetwood Mach Tribune Show. Experience the magic of Fleetwood Mac as Fleetwood Mach brings their iconic sound to life at Van Wezel Performing Arts Center on Saturday, May 3. This tribute show features all the legendary hits and Stevie Nicks favorites in a stunning look- and sound-alike performance.

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Westcoast Black Theatre Troupe

Running through May 25 Syncopated Avenue. WBTT presents Syncopated Avenue, its first original tap dance revue. This rhythmic, historical journey celebrates tap as a universal language, blending jazz classics by Ellington, Blake and Berlin with new compositions by Nate Jacobs, Lamont Brown and Louis Danowsky in an energetic exploration of dance, music and style.

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McCurdy’s Comedy Theatre

May 15, Matt Braunger. Matt’s comedy and acting credits span television hits including MADtv, Agent Carter, Disjointed, Upload, How to Be a Grown Up and more. With appearances on CONAN, Letterman, @midnight, and shows across HBO, Netflix, NBC and FOX, his versatile talent has made him a standout in comedy and television.

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Venice Theatre

May 19, for one night only – Sharon Owens – Tribute to Barbra. Sharon Owens channels Barbra Streisand in a captivating tribute spanning Broadway hits, disco anthems and film favorites. With uncanny vocals and charm, Owens brings the legend to life—offering audiences a heartfelt evening that feels like time spent with both Barbra and a rising star in her own right.

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Asolo Repertory Theatre

Beginning May 17, Jesus Christ Superstar. Apostles clash and faith is tested in Andrew Lloyd Webber and Tim Rice’s rock opera, Jesus Christ Superstar. Featuring iconic songs and a bold new production by Josh Rhodes at Asolo Rep, this reimagined classic examines love, betrayal and redemption under the heat of the Judean sun.

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Urbanite Theatre

Beginning May 29, From 145th to 98th Street. From 145th to 98th Street follows the Curtly family as they navigate ambition, injustice and identity after relocating from Harlem. When their son is falsely accused and their daughter questions her future, they must unite—or risk being torn apart by their pursuit of success.

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