Music Meets the Beach at Southwest Florida’s Island Hopper Songwriter Fest

Right off the coast of Fort Myers, Florida, lies Captiva Island – an exquisite island occupied with extraordinary wildlife, white sand beaches, delightful cuisine, and a rich music scene. The island is home to the Island Hopper Songwriter Fest. This 10-day music event features a wide range of top-charting composers to rising musicians looking to break into the industry. 

Country Now had the opportunity to see firsthand how the award-winning festival turned the quaint town into a lively atmosphere and why it quickly became a must-experience hotspot for songwriters.  

Music-goers, for instance, also travel near and far to sip on refreshing beach-centric cocktails as they praise the men and women behind their favorite radio hits. The beloved festival is divided into three locations – Captiva Island, downtown Fort Myers, and Fort Myers Beaches. The star-studded festival hosted by The Beaches of Fort Myers & Sanibel, BMI, IHeartMedia, and Cat Country 107.1 holds concerts in different locations, as they are looking to give vacationers and even locals a taste of what Southwest Florida has to offer. 

“It brings a fresh opportunity for not only residents but for visitors to come in and listen to a lot of new voices and music,” says a festival regular who has been attending the paradise-like event since 2014. “You’re sitting there listening, and all of a sudden, you’re like, ‘oh my God…you wrote that song? It’s like a No.1 hit!’ One of the best things is when you can actually sit and listen to each songwriter tell the backstory,” he mentions about the up close and personal experience. 

Throughout the 10-day event, music enthusiasts have the luxury to bop around to intimate outdoor restaurants and beach bars to enjoy sets and jam sessions from talented songwriters. At each casual venue, the organization pairs an up-and-coming songsmith with a notable name. While tourists and locals alike embrace the free concert, the budding artist receives a once-in-a-lifetime opportunity to pick the brain of the seasoned artist beside them. 

“All of sudden, your fantasy world kind of collides with your reality in that moment,” says Texas songwriter Leighton Fields about his experience performing alongside Aaron Barker – the man who penned several No.1 tracks for George Strait, Willie Nelson, and Lonestar. 

“I would not be where I am right now without this festival because being a local artist and then meeting writers who are your heroes and that treat you like equals makes you feel like you can do this and you can win. This is a tough game to be in, and we didn’t pick an easy job,” Keefe Klug, a rising artist from Fort Myers included to the conversation around the cut-throat stigma around being a hungry songwriter. 

As emerging writers turn to the veterans in the songwriter space for valuable advice, the creative minds behind the iconic tracks such as “The Good Ones” for Gabby Barrett, “You Don’t Know Her Like I Do” for Brantley Gilbert, or “My List” for Toby Keith attend the festival to learn from the fast-rising artists to keep up with the ever-changing demands from the music industry. 

“I take advice from them, and it’s very much a two-way street because it’s so easy to sit back, and the more success you have, the easier it is to try and ride on that success. And here comes these young songwriters with all this new language, rhythms, new thought processes, and if they are willing to share that with an old guy like me, my music and sound will come across as more contemporary,” says legendary writer Aaron Barker. “There are certain things that can be very helpful in writing. You know, the techniques and stuff, not to take away from the originality. However, I do think we help each other a lot,” he adds. 

Barker was not the only seasoned professional blessing festival-goer’s ears with his honest songwriting and honky-tonk sound. Hall of Fame lyricist Steve Dorff performed smash hits he created throughout the week for Whitney Houston, Anne Murray, Kenny Rogers, and Eddie Rabbit. Fans had the chance to stand in line and receive an autograph from the three-time Grammy nominee at his small ticketed concert and book signing. 

Before the festival became open to the public, songwriters and press rubbed elbows at a VIP party under the palm trees. While bonding over what makes a ‘great song,’ performers marched up to the mic to share toe-tapping melodies. For instance, multi-platinum writer Jim McCormick gave the cheering crowd chills with his male rendition of CMA nominated hit “The Good Ones.” In the middle of each private performance, everyone mingled amongst each other to pencil in which mini-concert series they should visit along the coast. 

During the downtime, music enthusiasts had the opportunity to jump in a kayak to explore Buck Key Mangrove, head to Cabbage Key by boat to enjoy a juicy cheeseburger from the local restaurant that inspired the classic tune “Cheeseburger In Paradise” by Jimmy Buffett, or even ride the waves on a jet ski with Sunny Island Adventures, which was quickly accessible on-site at the South Seas Island Resort.

To top off the 7th Annual Island Hopper Songwriters Festival, platinum-selling recording artist Jimmie Allen took center stage at Fort Myers Beach on Sunday, September 26, at the Pink Shell Pool Party. Before RaeLynn, Kristian Bush, and Maren Morris became the breakthrough stars we know today, they made their mark on the respected festival. Their influence on the industry leaves the aspiring musicians who attended the event hopeful for their future in the exciting, yet competitive music world.