Island Hopper Songwriter Fest return to Southwest Florida Sept. 18-27 which will conclude, as it does every year at The Pink Shell Resort on Fort Myers Beach. This year’s closing act at The Pink Shell has not been announced yet.
McCain is best known for hits including “I’ll Be” and “I Could Not Ask for More.” McCain had his major label breakthrough in the mid-’90s.
Most recently, McCain has been touring with Hootie & the Blowfish, Collective Soul and Train. Last year he was revealed as Nessy, the Loch Ness Monster during a run to the final five during Season 13 of the hit TV show, “The Masked Singer.” McCain will headline Island Hopper Songwriter Fest’s “Westin Unplugged” Monday, Sept. 21, at The Westin Cape Coral Resort at Marina Village in Cape Coral.
Alexandra Kay will also be part of the event this year. Kay is one of country music’s fastest rising artists earning millions of followers across social media. The BMI singer-songwriter recently released her sophomore album, “Second Wind,” and headlined her third tour featuring her single “Straight for the Heart.” Her debut album, “All I’ve Ever Known,” reached No. 1 on the iTunes All Genre and Country charts and earned her a Top 10 on Billboard’s Current Country Album.
Making its Island Hopper debut, Caloosa Sound Amphitheater will host the festival’s “Stars on the River” concert in downtown Fort Myers on Thursday, Sept. 24, featuring Alexandra Kay as the opening act.
In addition to the headlining performances, more than 60 BMI singer-songwriters will perform more than 80 performances during the 10-day music fest. Be sure to catch a live Island Hopper performance at these four locations around the Fort Myers area:
- Captiva Island, Sept. 18-20
- Cape Coral, Sept. 21-22
- Downtown Fort Myers, Sept. 23-24
- Fort Myers Beach, Sept. 25-27
While most Island Hopper shows are free, there are several ticketed events, including the Kay and McCain performances and the closing pool party at Pink Shell Beach Resort & Marina. Other one-of-a- kind ticketed experiences include a songwriter sunset cruise and dinner experiences.
Additional artists and schedules will be announced in the coming weeks.

