Southwest Florida sizzles with culture, creativity and entertainment this August. In Naples, an outdoor movie night brings the community together. In Estero, acrobatic athletes tumble through the air in a Cirque du Soleil performance. And in Fort Myers, Broadway Palm Dinner Theater puts on a timeless show for all ages. Don’t miss this month’s events.
Now through Aug. 9
Annie at Broadway Palm Dinner Theater, Fort Myers
The beloved musical brings optimism and heart to the stage with its timeless story of a spirited orphan determined to find her family. Featuring classic songs like “Tomorrow” and “It’s the Hard Knock Life,” the production combines lively choreography, endearing performances and Broadway-style flair in an intimate dinner theater setting. See More
July 31 — Aug. 3
Cirque du Soleil: OVO at Hertz Arena, Estero
Mind-bending acrobatics and interpretive aerial performances draw audiences into the secret life of bugs. Performers embody their insect counterparts with intricately pleated costumes inspired by French fashion designer Pierre Cardin and choreography from Deborah Colker, known for her work in the opening ceremony of the 2016 Summer Olympics. With a Brazilian-inspired soundtrack blending funk, samba, bossa nova and electronic music, the production’s revived tour features new staging and acts. See More
Aug. 1
The Peace of Woodstock at Gulf Theater, Military Heritage Museum, Punta Gorda
This tribute performance recreates the music of the 1969 Woodstock Music and Art Fair, featuring selections from artists such as Jimi Hendrix, Janis Joplin and Crosby, Stills, Nash & Young. With era-specific visuals and arrangements, the show reflects the cultural tone and sound of one of the most pivotal music festivals in American history. See More
Aug. 2
TikiFest at Fishermen’s Village, Punta Gorda
TikiFest showcases island culture with Hawaiian-inspired dance performances, steel drum music, tropical cuisine and themed beverages. The waterfront setting provides a festive backdrop for an event celebrating Polynesian traditions and summer rhythms in Charlotte County. See More
Aug. 7
The Bob Band: A Bob Dylan Tribute at Daniels Pavilion, Artis—Naples
The Bob Band presents a detailed interpretation of Bob Dylan’s extensive discography, with arrangements faithful to his original recordings. The performance spans Dylan’s early folk protest songs through his electric transition and beyond, offering an evening centered on one of America’s most influential songwriters. See More
Aug. 9
Fort Myers Roller Derby vs. Tampa Roller Derby at Fort Myers Skatium
The Fort Myers Derby girls host Tampa Roller Derby in a fast-paced flat track matchup. The evening features athleticism, strategy and full-contact play, with both teams competing for rankings in the Women’s Flat Track Derby Association. See More
Aug. 9
Gator Club of Naples Trolley Tour
This social event marks the beginning of the college football season with a trolley tour through several Naples venues, including Boston Beer Garden, Sea Monkey Tavern & Grill, Harold’s Place and North Naples Country Club. Attendees are encouraged to wear team colors, as the best-dressed fan earns a reward. The event provides an opportunity for University of Florida alumni and fans to connect. See More
Aug. 13
Rachmaninoff & Scriabin: Narrative Musicales at Artis–Naples
Two of Russia’s most expressive composers come to life in this grand piano performance. Part of the Artis–Naples Grand Piano Series, the evening explores the emotional landscapes of Sergei Rachmaninoff and Alexander Scriabin—composers whose distinct yet intertwined musical voices reflect late Romanticism and early modern mysticism. Audiences encounter lush harmonies, virtuosic passages and deeply introspective moments. See More
Aug. 16
Artisans & Oddities Market at Lee County Civic Center Complex, Fort Myers
More than 100 local vendors gather for a one-day event focused on handmade goods, eclectic art and metaphysical experiences like tarot readings and psychic consultations. Live music and food trucks are scheduled throughout the day. Proceeds support Access Art, a nonprofit focused on expanding access to creative opportunities. See More
Aug. 16
Bumpin Uglies & Kash’d Out at Sugarshack Downtown, Bonita Springs
Annapolis’ reggae-punk torchbearers, Bumpin Uglies, bring their gritty, genre-mashing sound to Southwest Florida alongside Orlando’s Kash’d Out, known for their polished blend of reggae, rock and pop. Kash’d Out, fresh off performances in other Florida cities like Fort Lauderdale and Sarasota, layers summery hooks with laid-back vibes, rounding out an evening that champions the evolving face of American reggae. See More
Aug. 19
Movies on the Lawn: Moana 2 at Mercato, Naples
Mercato’s open-air movie series continues with a screening of Moana 2, the sequel to Disney’s 2016 animated film. Families and fans can enjoy the continuation of Moana’s story under the evening sky, with seating on the lawn available on a first-come, first-served basis. See More
Aug. 21
EMBELLISHED Wearable Art Show, Bayshore Arts District, Naples
This juried fashion-meets-art showcase features handcrafted garments, sculptural accessories and multimedia designs created by local artists and makers. The event emphasizes craftsmanship, innovation and the expressive potential of wearable forms. See More
July 8 — Aug. 30
From Piccadilly Pub to The Pewter Mug: A Local’s Dining Experience Exhibition at Collier Museum at Government Center
This summer exhibition explores Naples’ evolving restaurant culture through archival photographs, vintage menus and memorabilia from beloved local eateries. Tracing the area’s dining history from 19th-century hotel cookouts to mid-century seafood joints and upscale establishments, the show presents a portrait of changing tastes and enduring favorites. See More