Island Hopper Songwriter Festival returns this weekend

Sep 15, 2026 By Nathan Mayberg 4 min read

Country musician Michael Ray will perform on Sunday, Sept. 27 at the Pink Shell Beach Resort and Marina pool party on Fort Myers Beach to cap off the Island Hopper Songwriter Festival. Photo provided

Everybody’s favorite Lee County music series gets going this Friday with the return of the Island Hopper Songwriter Festival. The festival will showcase more than 60 performers, including Grammy Award-nominated songwriters and chart-topping artists.

The first batch of performance will kick off on Captiva Island, before the performances move to Cape Coral and Fort Myers during the week, culminating in three days of music on Fort Myers Beach Sept. 25-27.

The festival will close out with a bang at the Pink Shell Beach Resort and Marina pool party on Sept. 27, featuring country singer Michael Ray. Ray is known for the country hit “Kiss You in the Morning.”

Now in its 12th year, the 10-day festival will feature more than 100 performances.

The Captiva Island shows will run from Sept. 18-20, followed by performances in Cape Coral from Sept. 21-22, downtown Fort Myers from Sept. 23-24, before reaching Fort Myers Beach for the final three days.

Fort Myers Beach will include three ticketed events. In addition to the Pink Shell pool party, there will be a “Music on the Mound” performance on Saturday, Sept. 26 featuring Frank Myers and Lauren Mascitti at the Mound House. Myers is known for co-writing the megahit “I swear,” which was recorded by John Michael Montgomery, and All-4-One. Mascitti’s album “God Made a Woman” reached #4 on the iTune country albums chart.

On that same day, the festival will hold a new ticketed event for Fort Myers Beach with the Sunset Songwriter Cruise out of Fort Myers Beach aboard Adventures in Paradise featuring singer/songwriter Robinson Treacher. “He has a great voice, great talent,” Lee County Visitor & Convention Bureau communications manager Miriam Dotson said. The bureau is one of the organizers of the event.

While tickets must be purchased for those shows, there will be a plethora of free music performances on Fort Myers Beach that weekend at Bayside Veteran’s Park, Diamondhead Beach Resort, Lighthouse Island Resort, Margaritaville Beach Resort, On the Bay, and the Yucatan Beach Stand Bar & Grill.

While most of the shows at the festival do not require a ticket and are free, other ticketed events include the new “Stars on the River” concert includes performances fom BMI singer-songwriters LOCASH and Alexandra Kay at Caloosa Sound Amphitheater on Sept. 23 in Fort Myers.

Captiva’s weekend will be highlighted by “Sunday Brunch” on Sept. 20 with Dylan Altman and Tim James at ‘Tween Waters Inn and Marina on Captiva. Altman has written three #1 country songs: Tim McGraw’s “Watch The Wind Blow By,” Jake Owen’s “Barefoot Blue Jean Night” and most recently Jason Aldean’s “Take A Little Ride.” James is known for writing the country top-charting hits “My List” by Toby Keith, “Give It All We Got Tonight” by George Strait, and “Love Like Crazy” by Lee Brice. James also wrote the Trace Adkins single “All I Ask For Anymore,” which was nominated for a Grammy Award for Best Country Song of 2009, and the 2010 Billboard Song of the Year.

The Gather in Cape Coral will be hosting a songwriter dinner with country musicians Bridgette Tatum and Alex Rohan on Monday, Sept. 21. Tatum is known for co-writing the chart-topper “She’s Country,” a song performed by Jason Aldean.

Other ticketed events include:

Sept. 21: Westin Unplugged featuring headliner and platinum-selling songwriter Edwin McCain at The Westin Cape Coral Resort at Marina Village.

Sept. 24: Luminary’s Dinner Experience with Nate Bass of British brother trio Essex County at Luminary Hotel & Co.’s culinary theater in downtown Fort Myers.

Sept. 24: ACMA Showcase with Roy Schneider, Anthony Wayne, Bill Metts, Tim McGeary and Matt Hannam at Sidney & Berne Davis Art Center in downtown Fort Myers.

The Island Hopper Songwriter Fest is presented by BMI, iHeartRadio’s Cat Country 107.1, Florida Restaurant & Lodging Association and Lee the County Visitor & Convention Bureau.

The Lee County Visitor & Convention Bureau is involved in organizing the event in conjunction with BMI and iHearRadio in a process that Dotson said involves “yearlong preparation.” the organization was excited about the addition of new venues this year, including the Caloosa Amphitheatre in Fort Myers, and the songwriter cruise on Fort Myers Beach.

“We are looking to get visitors to get to the restaurants, and drive some business,” Dotson said.

For the full lineup, schedule and ticket information, visit Islandhopperfest.com.