Things to Do in Naples and Southwest Florida This Weekend, September 25-27, 2026

 

The last weekend of September in Naples and Southwest Florida is a preview of the season ahead. Live music, comedy, a family fall festival and one final weekend of Sizzle Dining all share the same three days.

 

Date Night in Bonita Springs: Keys on Fire with Mia Vassilev

 

Arts Bonita Performing Arts Center hosts Keys on Fire with Mia Vassilev Friday and Saturday at 7:30 p.m. She has been compared to Liberace and Jerry Lee Lewis in a ball gown, and the cabaret style tables give the room the feel of a supper club. On Sunday, the same stage hosts Time Traveller: A Tribute to The Moody Blues at 7:30 p.m.

 

Live Music: Rock Republic at Sugarshack Downtown

 

Rock Republic is one of the most popular local bands in Southwest Florida, and they take over Sugarshack Downtown in Bonita Springs Saturday from 7 to 10 p.m. Friday night, The Broken Hearts bring their Tom Petty tribute to the same stage. Across the region, live music fills patios from Dogtooth Sports Bar in Naples to Snook Inn on Marco Island to Rusty's Raw Bar & Grill in Estero.

 

Family Fun: Farmer Mike's 12th Annual Fall Festival

 

Fall arrives in Bonita Springs on Saturday when Farmer Mike's U-Pick opens its 12th Annual Fall Festival & Corn Mazes. Families can explore a 5 acre corn maze with 16 game stations, pick pumpkins, sunflowers and wildflowers, and enjoy food vendors on site. Every ticket includes a free mini pumpkin. The festival runs Fridays, Saturdays and Sundays through October 31.

 

Comedy, Candlelight and Culture

 

Carlos Mencia performs at Off the Hook Comedy Cafe Friday through Sunday, and Joe Bartnick plays Snappers Comedy Cafe in Fort Myers. The Gulf Coast Symphony's Music & Arts Community Center hosts Candlelight: Queen vs. ABBA and 90s Hip-Hop on Strings on Friday, and The Conjurors bring magic to the same venue Saturday. Artis Naples offers a free chamber music concert Friday at 7 p.m.

 

Food, Markets and the Everyday Good Life

 

Sizzle Dining at Mercato wraps up September 30, so this is the weekend to book that table. LaPlaya Beach & Golf Resort hosts a Sunset Paint and Sip Saturday evening. Farmers markets fill Saturday and Sunday mornings at Third Street South, Vanderbilt, the Promenade at Bonita Bay and beyond. FC Naples plays at home Saturday night at Paradise Coast Sports Complex.

 

Why This Weekend Matters If You Are Considering Naples or Southwest Florida

 

Weekends like this show what life here actually looks like. Music, comedy, art, family traditions and great food, all close to home and close to the beach. It is not a vacation. It is how people live here, week after week.

 

If Naples has been on your mind, whether as a second home, a future move, or a place you are still getting to know, I am always happy to be a resource. Reach out anytime, or sign up for This Week in Paradise, my weekly guide to living, playing and owning in Southwest Florida, delivered to your inbox every Friday.

 

Diane Harris, Realtor and Luxury Properties Specialist

Serving Naples, Bonita Springs, Estero, Marco Island, Collier County, Lee County and the surrounding Southwest Florida area

 

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