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September in Southwest Florida is one of the hottest venues around.  We don’t mean the temperature, though it’s STILL plenty warm down here.  Captiva Island helps kick off the 6th Annual Island Hopper Songwriter Fest on September 20 – 23 before moving on to Fort Myers Beach and downtown Fort Myers. 

Sponsored by iHeart Media (and its local affiliate Cat Country 107.1 FM), The Beaches of Fort Myers & Sanibel, and BMI, the Fest brings over 100 phenomenal singer/songwriters for various small stage performances all over the islands and Fort Myers, from pool parties to workshops to restaurant/beach locations. 

Some of these performers have made quite an impact in multiple genres of music, from Rock to Pop to Country, working with superstars too numerous to list.  Some players are local, some are Floridian, and some are from all across North America. 

Here’s a sample of those performing on Captiva the weekend of September 20: 

Bill LaBounty (“Never Gonna Look Back” with James Taylor)

Bobby Tomberlin (“One More Day” with Diamond Rio)

Brandon Kinney (“Drowns the Whiskey” with Jason Aldean)

Bridgette Tatum (“Loud,” the Official Theme Song of ACC Football 2010)

Caleb Neff (Rosaline)

Carleen Thiessen (Women of Substance Radio, a Naples native)

Carlo Colasacco  (performed with Shinedown)

Dave Pahanish (“Without You” with Keith Urban)

Even Stevens (Dr. Hook, Kenny Rogers)

Sam James (competitor on “The Voice”)

And many more…

 Oh, and did we mention that many of these shows are FREE? 

For a full list of artists and shows for all 10 days in Southwest Florida, you can download the 2019 Island Hopper Fest app on either the App Store or Google Play.  Other information is available at

We hope you will enjoy the Songwriters Fest while “living like a native” in Sanibel Holiday’s condos.