Justin Willman: One for the Ages Tour arrives on May 1, 2026 at 7:00 PM, bringing a fresh, laugh-out-loud blend of magic and comedy to the stage in an all-new interactive experience perfect for all ages. Known for his hit Netflix shows Magic for Humans and Magic Prank Show, Willman combines mind-bending illusions with sharp, relatable humor in a performance that’s equal parts astonishing and hilarious. Fresh off his special Magic Lover, this high-energy tour features brand-new material, audience participation and unforgettable moments—making it an ideal night out whether you’re coming with family, friends or a date. 

Dvořák’s American Quartet closes the Wang Chamber Music series on May 3 at 3:00 PM in Daniels Pavilion, featuring musicians of the Naples Philharmonic in a program that beautifully blends global influences and traditions. The concert opens with a richly textured Piano Trio by Reena Esmail, inspired by both Hindustani classical music and Western chamber styles, before culminating in Antonín Dvořák’s beloved American Quartet, a warm and melodic masterpiece shaped by his time in the United States, offering audiences a vibrant and culturally rich chamber music experience. 

The Mahler Chamber Orchestra makes its highly anticipated debut on the Visiting Orchestras Series on May 3 at 7:00 PM in Hayes Hall, led by acclaimed pianist Yuja Wang, who also performs as soloist and director. This dynamic program showcases the ensemble’s versatility with Sergei Prokofiev’s lively Symphony No. 1 “Classical”, Alexander Tsfasman’s vibrant Jazz Suite for Piano and Orchestra, and Frédéric Chopin’s expressive Piano Concerto No. 1, blending elegance, wit and virtuosic brilliance into one unforgettable evening, with tickets also including same-day admission to The Baker Museum for a full cultural experience. 

Alice Cooper – Alice’s Attic Tour hits the stage on May 5, 2026 at 8:00 PM, delivering a legendary night of shock rock from one of the genre’s true pioneers. Known for his theatrical, horror-inspired performances—complete with guillotines, electric chairs and over-the-top stage effects—Alice Cooper brings his signature rock psycho-drama to life in a high-energy show that blends classic hits with his unmistakable dark flair. With a career spanning decades, countless iconic albums like School’s Out and Billion Dollar Babies, and a reputation as the architect of shock rock, Cooper continues to thrill fans old and new with a spectacle that’s as electrifying as it is unforgettable. 

The Miami City Ballet joins the Naples Philharmonic for a stunning performance on May 5 at 7:30 PM in Hayes Hall, led by conductor Gary Sheldon. This elegant evening of dance and live music features selections from Jewels, inspired by the work of George Balanchine with music by renowned composers including Gabriel Fauré, Igor Stravinsky and Pyotr Ilyich Tchaikovsky, showcasing the company’s signature blend of athleticism, precision and artistry; arrive early for a 6:30 PM prelude to enhance this captivating cultural experience.

The Mercato Nights Music Series returns on May 7 from 6:30 PM to 8:30 PM in the Piazza, featuring a live performance by Phenomenal Animal and their dynamic mix of soul, classic rock, funk and blues. This laid-back evening invites guests to enjoy great music under the open sky while grabbing cocktails, beer and refreshments from the event bar by The Pub or picking up takeout from nearby Mercato restaurants, making it the perfect midweek outing for music lovers and casual night-out seekers alike. 

The Bank of America High School Musical Awards takes place on May 8, 2026 at 7:00 PM, celebrating the incredible talent and dedication of local high school students both onstage and behind the scenes. Since 2008, this inspiring event has honored performers, musicians and production teams from schools across the region—including Bishop Verot Catholic High School, Fort Myers High School, Cypress Lake High School and more—recognizing their hard work, creativity and passion for musical theater. From standout performances to the countless hours spent rehearsing and building sets, the evening shines a spotlight on the next generation of artists in a lively, feel-good showcase. 

The Spring Concert featuring the Naples Philharmonic Youth Orchestra takes place on May 9 at 2:00 PM in Hayes Hall, offering a free, ticketed performance that showcases the talent and dedication of young musicians from across Southwest Florida under the direction of Manuel López-Gómez. This inspiring afternoon highlights a dynamic orchestral program (to be announced) and celebrates the next generation of artists, alongside “Drawing Inspiration: Creating Art to Music,” an engaging element that connects live performance with creative expression for a well-rounded cultural experience. 

Forever Motown takes the stage on May 10, 2026 at 7:30 PM, delivering a nonstop, high-energy celebration of the legendary Motown sound. Performed by a powerhouse cast of veteran entertainers—including former members of iconic groups like The Marvelettes and Main Ingredient, alongside seasoned Broadway performers—the show brings to life the timeless hits of artists such as Marvin Gaye, Smokey Robinson, The Temptations, The Supremes and Stevie Wonder. With authentic vocals, dazzling choreography, and period-perfect costumes, this electrifying production recreates the magic of an unforgettable musical era, featuring nearly 30 classic songs like “My Girl,” “Ain’t No Mountain High Enough,” and “Stop! In the Name of Love,” making it a feel-good, sing-along experience packed with nostalgia and soul. 

Jason Mraz: Still Yours arrives on May 13, 2026 at 7:30 PM, bringing an uplifting evening of feel-good music and heartfelt storytelling. A two-time GRAMMY® winner known for beloved hits like “I’m Yours” and “I Won’t Give Up,” Mraz delivers his signature blend of pop, folk and soul alongside special guest Gregory Page. Fresh off his album Mystical Magical Rhythmical Radical Ride and a standout run on Dancing with the Stars, Mraz continues to charm audiences with his optimistic spirit, smooth vocals and introspective songwriting, making this concert a warm, inspiring experience that celebrates both classic favorites and new music. 

Rhapsody in New York from the Grand Piano Series takes place on May 13 at 3:00 PM in Ubben Signature Event Space, featuring Valentin Kovalev alongside pianists Konstantin Soukhovetski and Milana Strezeva in a Narrative Musicales program that paints a vibrant musical portrait of New York City. Blending styles and eras, the concert includes works by George Gershwin, Sergei Rachmaninoff, Astor Piazzolla and Roberto Molinelli, weaving together jazz, classical and tango influences with spoken insights to create an engaging and expressive journey through the rhythms, energy and cultural spirit of the city. 

The Music of Horace Silver closes the All That Jazz series on May 13 with performances at 6:00 PM and 8:30 PM in Daniels Pavilion, featuring the Naples Philharmonic Jazz Orchestra performing the hard bop works of legendary pianist and composer Horace Silver. Led by artists including trumpeter James Suggs, the program highlights Silver’s signature blend of gospel, blues and soul-infused jazz, celebrating his influence as a founding figure of The Jazz Messengers and delivering an energetic, rhythmic, and soulful finale to the season. 

The timeless ballet Swan Lake comes to life on May 15 at 7:00 PM in Hayes Hall, presented by Naples Ballet with live accompaniment by the Naples Philharmonic under associate conductor Manuel López-Gómez. This production features student dancers performing alongside professional artists from American Ballet Theatre, bringing to the stage the iconic score of Pyotr Ilyich Tchaikovsky in a powerful story of love, betrayal and redemption, combining elegant choreography with sweeping live music for an unforgettable evening of classical ballet. 

Rodney Carrington brings his signature blend of stand-up comedy and country music to the stage on May 16, 2026 at 7:00 PM for a night of laugh-out-loud entertainment geared toward mature audiences. A multi-talented comedian, actor and platinum-recording artist, Carrington has spent more than two decades as one of the top-grossing touring comedians, with hit albums like Hangin’ With Rodney and Morning Wood, as well as his Netflix special Here Comes the Truth. Known for his edgy humor, storytelling and musical comedy, he delivers a high-energy show packed with sharp wit, hilarious songs and unforgettable moments that keep audiences laughing from start to finish. 

The Spring Chamber Ensembles Concert by the Naples Philharmonic Youth Orchestra takes place on May 16 at 4:00 PM in Ubben Signature Event Space, offering a free, ticketed performance that highlights the artistry of student musicians performing in small chamber groups. Under the direction of Manuel López-Gómez and coached by members of the Naples Philharmonic, these young performers showcase their musical growth and collaboration in an intimate setting that emphasizes the expressive power and close communication of chamber music. 

Sal Vulcano: Everything’s Fine Tour lands on May 17, 2026 at 5:00 PM, bringing an evening of sharp, relatable stand-up from one of comedy’s most recognizable faces. Best known for co-creating and starring in the hit series Impractical Jokers, Vulcano has built a massive following with his fearless humor and real-life storytelling, recently expanding his reach with his debut special Terrified and popular podcasts like Hey Babe! and Taste Buds. Fresh off a hugely successful tour that sold out major venues worldwide, this live show delivers the same off-the-cuff hilarity and candid style that fans love—packed with new material, big laughs and plenty of surprises.

Jim Breuer: Find The Funny Tour hits the stage on May 21, 2026 at 8:00 PM, delivering a high-energy night of laughter from one of comedy’s most enduring performers. Known for his breakout run on Saturday Night Live—where he created iconic characters like “Goat Boy”—Breuer blends sharp observations, hilarious family stories and spontaneous crowd interaction into a show that’s both relatable and wildly entertaining. With decades of stand-up success, viral comedy bits and appearances on major podcasts, Breuer continues to connect with audiences through his authentic, quick-witted style, reminding everyone that no matter what life throws your way, there’s always a way to find the funny. 

Patriotic Pops returns to Hayes Hall on May 21–22 at 7:30 PM, bringing together the Naples Philharmonic, the Naples Philharmonic Chorus, and the Naples Philharmonic Youth Chorus under associate conductor Manuel López-Gómez, with vocals by Broadway performer Julie Benko. This annual celebration features powerful orchestral and choral works by American composers, honoring service, resilience, and unity through soaring patriotic music and beloved national anthems in a stirring tribute to the American spirit.

Josh Gates Live! An Evening of Legends, Mysteries and Tales of Adventure takes place on May 22, 2026 at 8:00 PM, offering a thrilling, story-filled journey led by the charismatic explorer best known from Expedition Unknown and Josh Gates Tonight. Blending humor, suspense and real-life adventure, Gates shares unforgettable moments from his global expeditions—diving into ancient legends, unsolved mysteries and behind-the-scenes tales that bring audiences to the edge of discovery. From laugh-out-loud mishaps to awe-inspiring encounters, this live experience is perfect for fans of travel, history and the unknown. 

Community Day at Artis—Naples takes place on May 23 from 12:00 PM to 4:00 PM, offering free admission to the campus including Hayes Hall and The Baker Museum for a full day of art, music and family activities. Highlights include performances by the Naples Philharmonic Youth Orchestra (Youth Symphonia concerts at 12 PM and 2 PM), the Gulfshore Opera Harmony Choir at 1 PM, and the H.U.G.S. ukulele group at 3 PM, along with interactive art stations, storytelling, a musical instrument petting zoo, food trucks, and more, making it a vibrant, community-wide celebration of creativity and the arts. 

Side-by-Side brings together the Naples Philharmonic and the Naples Philharmonic Youth Orchestra on May 24 at 7:00 PM in Hayes Hall, conducted by Manuel López-Gómez for a powerful combined performance featuring nearly 100 musicians. The program includes works by Richard Wagner, Jacques Ibert, and Ludwig van Beethoven, culminating in Beethoven’s iconic Symphony No. 5, alongside a featured solo performance by flute soloist Miranda Leone, creating a thrilling showcase of mentorship, collaboration, and orchestral power. 

Art After Hours takes place on May 27 from 6:00 PM to 9:00 PM at The Baker Museum, offering free admission to museum exhibitions and an evening of art, music, and community at Artis—Naples. Guests can explore galleries throughout the evening while enjoying live saxophone music by Jim Blackburn and light refreshments at Heidi’s Place, making it a relaxed, family-friendly cultural experience that blends visual art with live performance.

Brincos Dieras brings his wildly entertaining, high-energy show to the stage on May 30, 2026 at 8:00 PM, delivering a bold blend of comedy, improvisation and audience interaction. Known offstage as Roberto Carlos Oliva Barajas, this larger-than-life performer has built a massive following with his colorful clown persona, fearless roast-style humor and anything-goes approach that keeps every show unpredictable and unforgettable. With sharp wit, outrageous antics and constant crowd engagement, Brincos Dieras turns each performance into a full-on comedy spectacle packed with big laughs and vibrant personality.

Enjoy live music under the evening sky at Sounds on Strada, happening every Saturday from 6–8 PM through May 30 at the Piazza in Mercato. This weekly outdoor series features talented local musicians performing in a relaxed, open-air setting perfect for a casual night out. Upcoming performances include Wendell Ray (April 4), Roman Fortune (April 11), The Kelly & Mason Duo (April 18), Brad Allison (April 25), Wendell Ray (May 2 & 9), The Kelly & Mason Duo (May 16), Claire Liparulo (May 23), and Reckless Saints (May 30), offering a variety of sounds to enjoy while you unwind, stroll the shops or grab dinner nearby.

Beautiful: The Carole King Musical – Broadway musical at Gulfshore Playhouse though May 31 with multiple showtimes (some sold out). This triumphant show tells Carole King’s inspiring story from teenage songwriter to voice of a generation, featuring hits like “You’ve Got a Friend.” Tickets are $39 to $119. 100 Goodlette-Frank Road South, Naples. 239-261-7529 or gulfshoreplayhouse.org.

Jazz Concert – The Jazzmasters perform at The Norris Center from 1-3 p.m. every Saturday. Free admission, but donations are appreciated. 755 8th Ave S., Naples. 239-213-3058 or www.naplesgov.com/parksrec/ page/norris-community-center.