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The annual Island Hopper Songwriter Fest is a series of intimate performances in multiple settings from mid to late September, part of which includes our neighboring Captiva Island.  Presented by the Lee County Visitor and Convention Bureau, iHeart Radio, and BMI Music, featuring over 70 singer-songwriters and over 100 shows.  Some are among Nashville’s finest but also got their start locally.


This year’s Fest looks to be one of the biggest yet, with performances by some stars as Sheena Brook (from Fort Myers Beach and a contestant on “The Voice”), Kristian Bush (one half of Sugarland), Adam Ezra (famous for his NSFW parody “The Devil Came Up to Boston”).  It all builds up to a headliner performance by Gary LeVox, best known as the frontman for pop country superstars Rascal Flatts! (Sunday, September 25 at 5:00 pm)


Most shows are free with the exception of the Gary LeVox concert and a few special events.  Attendees are encouraged to go to the Island Hopper website or download the app for your mobile phone to purchase tickets or register for certain limited capacity events.  The site updates its schedule and also allows you to customize the schedule to the shows you don’t want to miss.  It also offers advice on parking (as Captiva parking can be quite limited) and transportation options and offers special deals at area hotels (in Captiva’s case, save by staying at the Sundial Beach Resort on Sanibel).

Island Hopper Fest App


Downloading the app also enters you for a chance to win a two-night stay at The Pink Shell Resort, tickets to the LeVox concert and a $200 gift card!


The festival kicks off on Captiva September 16 – 18 in the following traveling order up Captiva Road:


Tween Waters Island Resort (poolside; call for parking status)

The Green Flash

On Andy Rosse Lane… Key Lime Bistro, RC Otters, The Mucky Duck,

Doc Ford’s Rum Bar and Grille (at Chadwick’s Circle, just before the gate at South Seas Island Resort)

South Seas Island Resort (restricted to resort guests only)


From September 19 – 22, concerts move to the downtown Fort Myers area:


The Luminary Hotel & Co.

City Tavern

Sidney & Berne Davis Art Center

The Social House

The Barrel Room

Twisted Bistro


The Fest finishes up the next weekend (September 23 – 25) on Fort Myers Beach, most of which (but not confined to) in Times Square:


Pinchers Tiki Bar & Grill (at the Wyndham Garden Fort Myers Beach)

Cabañas Beach Bar and Grille (at the DiamondHead Beach Resort)

Pierside Grill and Famous Blowfish Bar

Nervous Nellie’s

Matanzas on the Bay

Pink Shell Beach Resort and Marina (standing room only for the Gary LeVox concert)


We hope you enjoy this end-of-summer tradition!


Book Direct and Save…and get Hoppin’!