Get ready for a weekend of live music under the stars! The Island Hopper Songwriter Fest wraps up its 2026 run right here on Fort Myers Beach, September 25–27, and it’s one of our favorite reasons to plan a late-September getaway. Free, intimate, and packed with talent — here’s what to know before you go.
What Is the Island Hopper Songwriter Fest?
Now in its 11th year, the Island Hopper Songwriter Fest brings 60+ acclaimed BMI (Broadcast Music, Inc.) singer-songwriters to more than 20 intimate venues across Fort Myers and the surrounding islands. The festival kicks off September 18 on Captiva, moves through Cape Coral and downtown Fort Myers, then closes out its final weekend right on Fort Myers Beach — making late September the perfect time to be here.
What to Expect on Fort Myers Beach
The Fort Myers Beach leg of the Island Hopper Songwriter Fest (September 25–27) spreads free performances across beachside bars, resort pools, and waterfront restaurants up and down the island. Most shows are completely free to attend — just grab a seat, order a drink, and enjoy some of the best up-and-coming and established songwriters in the business performing their own hits in a laid-back, unplugged setting. A few special ticketed experiences are also on offer, including sunset cruises where a BMI songwriter shares stories and songs as you glide along the water at golden hour.
Tips for Catching a Show
Because performances are spread across so many venues, it’s worth checking the festival’s official schedule before you head out for the night — sets can fill up fast at the smaller spots. Arrive a little early for the popular beachfront venues, and don’t be afraid to island-hop between a few different shows over the weekend; that’s half the fun of it! For the full lineup, venue map, and ticketed experience details, visit the official Island Hopper Songwriter Fest guide from Visit Fort Myers.
Make It Your Home Base for the Weekend
With music venues scattered up and down the island, a Fort Myers Beach vacation rental puts you within walking or golf-cart distance of most of the action. Not sure which shows to prioritize or where to grab dinner between sets? Our concierge team is happy to help you build the perfect festival weekend itinerary. For more on what else is happening around the island this September, check the Fort Myers Beach Chamber’s events calendar.
Ready to catch the music? Reach out to our team and let’s get your Island Hopper weekend booked!
Photo by Uday Vatti on Unsplash
