One of Southwest Florida’s hidden gems is the Island Hopper Songwriter Festival. It takes place September 18–27, 2026, across Captiva Island, Cape Coral, downtown Fort Myers and Fort Myers Beach. The 10-day Southwest Florida music festival features 60+ free performances by BMI singer-songwriters in intimate venues throughout the Fort Myers area.
When Is Island Hopper Songwriter Fest 2026?
The Island Hopper Songwriter Fest takes place September 18-27, 2026, unlike other music festivals that last a few days.
- Captiva Island — Sept. 18–20
- Cape Coral — Sept. 21–22
- Downtown Fort Myers — Sept. 23–24
- Fort Myers Beach — Sept. 25–27
Where Is Island Hopper Songwriter Fest Held?
It’s spread across four locations in Southwest Florida: Captiva, Cape Coral, downtown Fort Myers, and Fort Myers Beach. It’s comfortable, affordable, and rejuvenating. Explore this beautiful slice of paradise while discovering tons of new music. Couple it with a Royal Shell rental, and vacation doesn’t get much better than this.
The annual Island Hopper Songwriter Fest is also the biggest festival in Southwest Florida that’s dedicated to all things songwriters. The best part? The event is mostly free, save for a few performances that require tickets.
Island Hopper began in 2014 and continues to grow each year. With venues downtown near Fort Myers vacation rentals, Fort Myers Beach vacation rentals, Captiva Island vacation rentals, and Cape Coral, the annual Island Hopper Festival gives everyone a chance to catch a variety of musical acts.
The festival, which takes place September 18-27, 2026, also helps boost the local economy. Each year, local shops and restaurants see an uptick in business during the event, and it gives Southwest Florida visitors a chance to see what this part of the Sunshine State is all about.
The festival is presented by the Lee County Visitor & Convention Bureau, Florida Restaurant and Lodging Association (FRLA), iHeartMedia, and BMI. It’s meant to bring people together through music while shining a spotlight on area bars and restaurants. Attendees will be able to enjoy nearly 60 artists, most of which are free and in small, intimate venues across downtown Fort Myers, Captiva Island, Cape Coral, and Fort Myers Beach.
Island Hopper Songwriter Fest 2026 Lineup and Headliners
The 2026 Island Hopper Songwriter Fest lineup includes Edwin McCain, who will headline at The Westin Cape Coral Resort on Monday, September 21. Alexandra Kay will open the show at Caloosa Sound Amphitheater on Thursday, September 24. More headliner announcements are expected, and the full schedule is typically released closer to the festival.
Past featured artists include Chris Young, Scotty McCreery, Kristian Bush, Chris Janson, Gone West, Jerrod Niemann, Rodney Atkins, and Ryan Hurd. Check back every year to learn about the exciting music lineup!
Where should I stay for Island Hopper Songwriter Fest?
Travelers can stay in Captiva Island, Fort Myers Beach, Cape Coral, Fort Myers, or nearby Sanibel Island vacation rentals, depending on which festival dates and venues they plan to attend. Royal Shell has a variety of rental homes available on Captiva Island, Fort Myers Beach, and in Fort Myers. They come in all shapes, sizes, and colors. Whether you’re coming with a lot of friends and family or you’re looking for a romantic getaway or a low-key retreat with close friends and family, Royal Shell can accommodate any vacation. Our Vacation Planning Advisors offer optimal customer service, can help you plan your vacation, and can answer any questions you have about the Island Hopper Songwriter Fest.
For more information, you can also download the official Island Hopper mobile app for iOS and Android devices. You can use it to purchase tickets for select performances, look up artist information, updates and alerts, and performance times and venues.
