Behind the Music: The Artists of Island Hopper Songwriter Fest

Discover what the Island Hopper performers and musicians love about the islands, beaches and neighborhoods of Fort Myers. 

Every year, Island Hopper Songwriter Fest celebrates the artistry of music beyond the big stages. Songwriters and performers tell the stories behind the songs that they’ve penned, taking place over 10 days throughout Southwest Florida in Fort Myers Beach, downtown Fort Myers, Cape Coral and Captiva Island. Discover the intimate venues that they love to play, as well as the bars and restaurants where they like to eat and drink, and other favorite local spots that keep them coming back.

Vinny Hickerson

As a regular performer at the festival, Vinny Hickerson holds a fond place in his heart for Fort Myers — so much that he proposed to his now-wife on stage at the event!

“I wanted to do something special, and my wife is a phenomenal harmonica player. I knew there would be a moment when she was going to join us on stage, so I thought, ‘Here’s my chance.’ As soon as I got down on one knee, the crowd started cheering."

Since he’s been coming to Island Hopper for several years, Vinny has watched the event grow and evolve but appreciates that it has retained its authenticity.

“I love the fact that they bring in all different types of artists who play all different genres — it’s not just the same faces that play every other festival. There are a lot of up-and-comers who have a chance to play in front of crowds and see how their songs hit. It’s literally my favorite songwriters festival that I’ve ever been a part of.”

Bryan Ruby

A pro baseball player turned country artist, Bryan Ruby grew up visiting family in Fort Myers, and it was his grandpa who first introduced him to the Island Hopper Songwriter Fest.

“I play about 80 shows a year, and Island Hopper is really one of my favorites because it’s such a cool environment and so relaxed. In other festivals, there can be a barrier between artists and fans, but here we’re totally immersed.”

One of Bryan’s favorite venues to play is the Yucatan Beach Stand Bar & Grill, but he points out that nearly every show has a friendly and intimate atmosphere. “Since most of the shows are free, you can come and go as you please. You’re never stuck in a packed crowd, you can go to two shows or 15 shows, and it’s a strong community-building event for Fort Myers.”

Megan Linville Myrick & Danny Myrick

Megan and Danny Myrick are both grateful to be able to tour together often — and they’re one of the handful of artists who have been a part of the Island Hopper Songwriter Fest since its inception.

“Island Hopper is very, very unique in that it has multiple locations and runs for 10 days,” says Danny. “There’s something about the small-town vibe and the sense of community. From year one, we’ve met people at the festival who have become close friends, and we love catching up with our friends from Nashville.”

As individual performers, they’re both well-acquainted with venues around the area, including the Yucatan Beach Stand Bar & Grill and Pink Shell Beach Resort & Marina. As a couple, they have their favorite rituals whenever they’re in town for the event.

“Our tradition is that we’ll leave downtown, walk the beach and stop at Yo! Taco. Usually a bunch of us will head to the bar at DiamondHead,” says Danny.

Megan, an avid seashell collector, always carves out time to walk the beach on her own as well. “My grandmother was a biology teacher, so when I was growing up, she taught me about all the seashells. I’ll listen to music or just be silent; it’s my Zen time and it’s what I love to do.”

Nate Bass

As one the three brothers behind the band Essex County, Nate doesn’t encounter too many Brits at Island Hopper — but he’s thrilled to be part of BMI’s Nashville crew that plays in Fort Myers every September. 

“We’ve all played pub gigs in our career, where you’re just noise in the background. But what I love about Island Hopper is that people are coming to Fort Myers specifically to listen to your creations. That’s what’s so beautiful about the event in its entirety.” 

Once the shows wrap up for the night, Bass reveals that all the musicians wind up at DiamondHead Beach Resort on Fort Myers Beach. “They set up a stage on the pool deck and everyone becomes a karaoke star just jamming out.”

Timothy James

A number-one songwriter and performing artist whose early career included pharmaceutical sales and painting houses, Timothy James knows a thing or two about imposter syndrome — but his dedication to writing led to his success in Nashville.

“There’s a difference between being a musician and a commercial songwriter [and Island Hopper] is an experience to see the people who write the songs. I had a number one song by Lee Brice, ‘Love Like Crazy,’ and it’s about my dad dying. It’s tough for me to get through, and people feel that when I perform it.”

As a California native, Tim naturally gravitates toward the sand and the water that Southwest Florida is known for. “The whole vibe in Fort Myers Beach is cool, and Captiva Island is so laid-back — I’ve taken my daughters there to collect seashells. I’ve done this event for so long that it feels like a vacation every September!”

Frank Myers

Award-winning singer-songwriter from Nashville, Frank Myers also loves the laid-back vibe on Captiva Island. “You can chill on the beach or at the pool, go fishing or take a boat ride, and the food selections are many. My personal faves are The Green Flash, Old Captiva House and the Crow’s Nest!”

Come listen to these and other amazing singer-songwriters at the Island Hopper Songwriter Fest, taking place September 19–28, 2025. Plan your trip with special deals just for the festival.