Skip to main content

Times of the Islands Magazine

Music on Your Mind?

Sep 03, 2025 07:00AM ● By Ann Marie O’Phelan

If you love music, mark your calendar for September 19-28, 2025! It’s the 11th annual Island Hopper Songwriter Fest that takes place in various venues in Southwest Florida, including Captiva Island (19-21st), Cape Coral (22nd-23rd), Downtown Fort Myers (24th-25th), and Fort Myers Beach (26th-28th). The 10-day festival was ranked in 2024 by USA Today as the 4th best music fest in the country by Reader’s Choice Awards. That’s no surprise as this festival draws exceptional talent from all over the country.

Credit images to: Fort Myers - Islands, Beaches and Neighborhoods.

This year’s highlights include “A new partnership with Cut the Chord string quartet for a unique listening experience featuring BMI singer-songwriter, Frank Myers and Jimmy Nichols at the Captiva Civic Center on Saturday, September 20th at 2 p.m. Also, an event called “Canvas and Chords”. Danny Myrick and Katrina Cain will perform on Fort Myers Beach at Alair Custom Homes on Saturday, September 27, at 4 p.m., while a local artist, Lacy McClary, paints a work of art. Proceeds will support SWFL Reefs,” explains Miriam Dotson, Communications Manager, Lee County Visitor & Convention Bureau.

Over 60 events are free to the public; however, some headliner and specialty shows require advance tickets. For the full lineup, lodging deals, and ticket information, visit IslandHopperFest.com or download the Island Hopper app, available on the website. Also on the website, check out musical artists’ bios and find out when and where they are playing.

“Island Hopper is a unique experience because you get to get up close and personal with the best singer-songwriters who write for the biggest names in country music. It’s like they are singing directly to you! With the tropical backdrop mixed with great music, food, and friends, what else can you ask for?” adds Dotson.

Additionally, the September Music Walk takes place from 6-10 p.m. on Friday, September 19, 2025, in the historical River District of Fort Myers (First Street and Hendry Street). The area comes alive with live music every third Friday of the month. The event is free to the public with over a dozen participating venues featuring rock, pop, country, jazz, and more, by local and regional talent. Plus, many of the restaurants are open during the event.  It’s another popular music event in SW Florida!

Ann Marie O’Phelan is a SW Florida resident and a regular contributor to TOTI Media.