On the first Friday of the 2018 Island Hopper Songwriter Fest in Captiva, a dozen volunteers dressed in shorts and T-shirts gathered at the headquarters, hugging and chatting excitedly like counselors reuniting at summer camp after a year apart. After eyeing the scene for a moment, a friend and I hopped on a golf cart and sped toward Captiva’s tiny downtown, weaving around groups of people streaming in and out of hotels and restaurants, which were transformed into music venues for the occasion. Country musicians played from morning until midnight.
Before the festival got its start in 2014, this stretch of Southwest Florida was sleepy in September. The sweltering shoulder months brought the low season. The county wanted to attract visitors and drew inspiration from Key West’s 22-year-old songwriter festival—one of the largest in the world—to create a similar event. The organizers called up BMI, the musician association that also sponsors the Key West fest, to help produce and sponsor the event.
Word started spreading that for 10 days in September, Southwest Florida turned into mini Nashville with dozens of country music songwriters playing more than 150 shows (most of which are free) along the beaches. After hearing people buzz about Island Hopper for years, last September I joined over 18,000 festivalgoers for the event’s fourth installment. By then, the crowd was already more than three times the size of what it was in its first year.
Island Hopper bills itself as a country music festival, but the “country” and “songwriter” notions are loose enough to appeal to anyone who likes watching talented musicians play somewhere other than an oversized concert hall. Some of the musicians are famous (Country Hall of Famer Even Stevens, Spin Doctors’ Chris Barron), while others are the geniuses that work behind the scenes to write songs we love to sing along to on the radio. You might not know their names, but you know their tunes. All the performers have one thing in common: They write their own music. Shows range from small listening sessions to productions you’re not likely to catch anywhere else. This year, I’m especially looking forward to seeing Sugarland’s Kristian Bush perform with the Gulf Coast Symphony.
Some of these acts are local, but many come from out of town and stay in homes offered up by local realtors and hoteliers. The charming beachfront cottage and bed-and-breakfasts often turn into venues where the
songwriters host intimate performances—one of the many things that makes this event more special and grown-up than the average millennial music festival.
Last year, on a Saturday night in Captiva at Doc Ford’s Rum Bar & Grille, songwriting legend Aaron Barker and Trick Pony’s Heidi Newfield were well into their show when we arrived at 8 p.m. The bar was standing-room-only. At a table in front of us, a little boy was asleep across two chairs that were pushed together. His place was set for a child’s version of a nightcap: little cars, Legos, a book. Plenty of other families were packed in the iconic bar, too. The boy slept through Barker’s famous Blue Bell Ice Cream jingle, as well as the song he penned that earned George Strait a No. 1 on Billboard’s country charts in 1991, “Love Without End, Amen.” Barker said he wrote the song after he reprimanded his son one night. He wanted to reassure the boy a father’s love is unconditional.
Fittingly, the little boy’s parents started to sing along. And while I never considered myself a country music fan, I couldn’t help but sing right along with them.
STRAIGHT FROM THE SOURCE
Four local musicians share insight on how to do Island Hopper right.
Fort Myers gal who competed on “The Voice” Season 12
“Park for free on Fort Myers Beach on the opposite side of the Matanzas Pass Bridge, and then rent a bike or golf cart from one of several peddlers. For a good show, Key Lime Bistro has a really fun crowd.”
Naples musician who toured with Billy Idol and Depeche Mode
“On the last day of the festival, don’t miss the jam session that takes place at Diamondhead Resort. Almost all of the musicians come together.”
Captiva artist known as the Outlaw Songster
“Whether it’s coffee or beach supplies, Bailey’s General Store on Sanibel Island is my go-to for anything at any time.”
Lead singer of the Cape Coral band Rosaline
“Cantina Captiva is the place to post up later in the evening if you’re looking for a more intimate venue. Last year, there were only 10 or 15 people when I was on stage, and it was just perfect.”