Island Hopper Fest Connects Songwriters with Music Fans in Fort Myers and Sanibel

Island Hopper Fest, a 10-day songwriter festival in Southwest Florida, returned for its fourth year in September. Living up to its name, Island Hopper is located in three different settings — Captiva Island, Downtown Fort Myers and Fort Myers Beach — and includes performances by 85 songwriters beside a picturesque backdrop.

Sounds Like Nashville traveled to Fort Myers Beach on Friday (Sept. 29) to attend the final three days of the festival where we caught numerous writers rounds, interviewed several songwriters and learned the stories behind many of their hits. Held less than a month after Hurricane Irma devastated Florida, the festival also served as a fundraiser to help those affected by the storm in the five surrounding counties.

Island Hopper Fest was first conceived as a way to bring an economic impact to the Fort Myers and Sanibel communities in late September when the busy beach season came to a close. Tamara Pigott, Executive Director of Lee County Visitor & Convention Bureau, told Sounds Like Nashville that after their marketing director visited the Key West Songwriters Festival the wheels were set in motion to create a songwriters festival of their own while partnering with BMI and iHeart Media.

“We wanted it to be Island Hopper,” Pigott explained. “What makes the beaches of Fort Myers and Sanibel unique is we have all these little islands. So, we knew that songwriters would want to come and have a little respite on the beach. We had a beautiful spot that we could entice them and [it was] a way to deliver heads and beds in September and retain our community.”

Maggie Rose; Photo credit: The Beaches of Fort Myers & Sanibel

The festival has grown significantly over the past four years with an estimated 15,000 in attendance in 2017. As a result, many of the venues around Fort Myers Beach were standing room only throughout the festival’s final three days. And despite the crowds, Island Hopper had an attentive audience. Songwriter Brandon Kinney (Randy Houser’s “Boots On,” Craig Campbell’s “Outta My Head”) took part in the festival for the third year and compared it to a small CMA Fest for songwriters.

“People that actually know that songwriters are behind the songs, they’re the ones that want to come see it and they come from all over,” Kinney explains. “I enjoy getting to meet people that love country music. It’s good for me to get out and play songs for people who love country music.”

Kinney’s sets throughout the weekend included a mixture of radio hits, unreleased songs currently on hold by artists like Jason Aldean and Jon Pardi, as well as some of his more comical material. On Friday evening he was joined by Tim James (Lee Brice’s “Love Like Crazy,” George Strait’s “Give It All We Got Tonight”) at Sunset Beach Tropical Grill for an hour showcase where the two friends traded jokes and hit songs for festival-goers. Prefacing his performance of “Outta My Head,” Kinney shared that Craig Campbell recorded the song a month after he wrote it and released it as a single three months later, something he said “doesn’t ever happen.”

By contrast, at a writers round later in the weekend Frank Myers explained that it took six long years before his song, “I Swear,” was recorded by John Michael Montgomery and later R&B group All-4-One.

“Everybody passed on this song in town,” he said while performing at DiamondHead Beach Resort on Sunday afternoon (Oct. 1) with the scenic white sands beach set behind him. “All the big names at the time — Alabama, Kenny Rogers — you name it.”

Myers recalled visiting Montgomery’s family to play the song and walked into the singer’s home in Lexington, Ky., where his mother, father, older brother Eddie and his Montgomery Gentry bandmate, Troy Gentry, were seated at the table. He played the song three times, eventually convincing Montgomery to cut it.

“It was the last song he did on the recording session. From my understanding, the producer didn’t want to do it but John Michael did,” he added. The song would go on to be a four-week No. 1 for the singer and spend an incredible 11 weeks at No. 1 for All-4-One.

There were many stories like this told throughout the festival. George Ducas, an artist and songwriter who has penned hits for Eli Young Band (“Always the Love Songs”), Sara Evans (“Real Fine Place To Start) and Josh Thompson (“Won’t Be Lonely Long”), among others, shared a tale of writing a song about beer one night on Music Row, never thinking it would see the light of day. “No one needs another song about beer,” he said during his energetic set at DiamondHead Beach Resort the previous night. He later learned that Garth Brooks wanted to record the song, aptly titled “Beer Run,” and make it a duet with George Jones. The song would go on to be nominated for a Grammy. Evidently, he was wrong about the need for another beer song.

While the festival highlighted many hit songwriters, it also embraced newcomers. Artists like Kaylee Rose were humbled to share the stage with songwriters who penned some of their favorite songs. The 21-year-old Florida native said performing on the beaches of her home state was a rewarding experience after moving to Nashville just three years ago. While Rose is seasoned playing bars and venues throughout Florida and Tennessee, she says she appreciated the intimate and attentive setting Island Hopper Fest provided.

“It’s more about the stories behind the songs rather than the show itself,” the singer, who released her debut EP in August, said before her performance at Sunset Beach Tropical Grill Saturday afternoon. “I think that’s something really special. We write these songs from experiences and we always want to share them but we can’t at every show. My favorite part of these songwriters festivals is that people come not to just hear music, but they also want to know why I wrote these songs.”

During our chat a new fan who saw the singer the night before approached Rose about buying a CD. The singer sold out of copies her first night performing at the festival and was pleasantly surprised by the crowd’s reaction to her showcase.

“I’ve been playing more of my storytelling songs because people are really intrigued by it here,” she explained. “It’s a great crowd. More attentive than the typical bars you play at and these are bars, but there’s a different energy here.”

Phillip White and Lance Carpenter; Photo credit: The Beaches of Fort Myers & Sanibel

While the 10-day festival provided endless shows for music fans, it also served as a beachside writers retreat for some of the songwriters. Lance Carpenter, an artist and songwriter who co-wrote Kelsea Ballerini’s “Love Me Like You Mean It,” finished writing two songs while staying in Fort Myers Beach. One of those songs, “I’ll Stand,” which he started in Nashville with Philip Pence, he debuted during his performance Saturday night.

“It takes an issue that has been very hot lately with the whole NFL and kneeling during the anthem,” he said hours before his concert while seated at a table on the beach. “I left the military and I left football out of it. I wanted to write a song that 10 years from now, when this issue is all said and done, this song can still mean something to someone. I wrote it from the perspective of the flag so the flag is actually singing the song to the people.”

A powerful performance, Carpenter hushed the crowded venue with his new song. “I’ll stand for you / I’ll stand for us / American daughters and American sons / Forever free, in God we trust / You stand for me and I’ll stand for us,” he sang on the chorus. His set included tracks from his latest EP, Mustang, as well as another memorable song called “Things That You Don’t Miss” which Tyler Farr recently recorded for his third studio album. As he explained in an interview before his set, it’s the intimacy of Island Hopper Fest that allows him to debut these types of story songs.

“I do a lot of different songwriters festivals and I love the intimacy of this one. You actually get a chance to spend some quality time with writers that you may not have the chance to spend time with in Nashville if you’re on the road a lot,” he shared. “I don’t feel like I’m trying to run from place to place to catch certain shows because they’re all pretty close to each other and there is a little time in between so you can watch one show and tab out and walk to the next show.”

This environment allowed many of the songwriters performing to showcase their more vulnerable music. Acts like Maggie Rose and Skye Claire, who performed together at Nervous Nellie’s Friday evening, shared their struggles and successes during an engaging hour-long set.

Prefacing her soulful song “Too Many Love Songs” off her latest EP Dreams > Dollars, Rose admitted to writing the song from a place where she was brokenhearted. “I figured, even the love songs are daggers to the heart. They’re supposed to be happy but from a perspective it can be a bummer to hear a love song so I wrote this,” she told the audience at the rooftop restaurant.

Skye Claire; Photo credit: The Beaches of Fort Myers & Sanibel

Skye Claire shared a similar experience with her catchy “Bleach and 80 Proof.” As she explained, women often get over a bad breakup with highlights and alcohol. She put herself into the song with her drink of choice — Jack Daniels.

Additional highlights throughout the festival included a round of female duos on Friday evening. Reverie Lane and Granville Automatic shared the stage at Nervous Nellie’s in Fort Myers and showcased mesmerizing harmonies as they traded jokes and anecdotes behind their band members. At one point Granville Automatic’s Elizabeth Elkins shared a unique fact about her bandmate Vanessa Olivarez.

“A little unknown Granville Automatic secret that I decided to randomly spill lately is that she actually was the original singer of a band called Sugarland and she wrote this with those guys,” Elkins said before the duo performed a song called “Sugarland” that the country band of the same name featured on their second studio album, Enjoy the Ride. The duo also had a hand in penning Billy Currington’s previous single, “Drinkin’ Town with a Football Problem.”

Reverie Lane, made up of Presley Tucker and Spencer Bartoletti, also impressed with their striking harmonies and story songs. Tracks like “South of Sober” left a mark with lyrics including, “Lovin’ with your heart wide open / Is a damn good way to get it broken.” The daughter of Tanya Tucker, Presley, and bandmate Bartoletti, forge a unique musical path of their own as a duo.

Raelynn; Photo credit: The Beaches of Fort Myers & Sanibel

RaeLynn closed the festival with a sunny poolside concert at Pink Shell Beach Resort & Marina on Sunday afternoon where she performed several tracks off her No. 1 album WildHorse and shared her love of songwriting. Several songs into her 40-minute set, the singer told the story behind her heartbreaking last single, “Love Triangle.”

“I wrote ‘Love Triangle’ when I was 18 years old about my perspective of my parents’ divorce and how it felt to be stuck in the middle of the two people you love the most — your mom and your dad,” she told the audience. “Songwriting has always been a way for me to get through things. I don’t really process something or get through it until I’ve written about it.”

A festival centered around shining a light on songwriters and their songs, Island Hopper Fest proved to be an inspiring festival for both the artist and the listener.