The popular songwriter fest returns to Southwest Florida! Now in its 12th year, the 10-day Island Hopper Songwriter Fest once again brings amazing performances by top-notch singer-songwriters from Nashville, nearby, and nationwide. The festival takes place from September 18 through September 27, 2026, in four locations, with the first stop at Captiva Island, then Cape Coral, then downtown Fort Myers, before wrapping up on a weekend on Fort Myers Beach. Some of the artists that will perform in Cape Coral include noteworthy singer/songwriters Locash, Alexandra Kay, and Anthony Wayne. Besides the many locations making it easy to attend a local show or two, the majority of the 60+ shows are free, so it’s also an easy-on-the-budget experience. Special ticketed experiences are also offered, such as the Pink Shell Pool Party on September 28, 2026. Music lovers can stay up-to-date on festival news by joining the email list, downloading the official festival app, or following the Island Hopper Songwriter Fest’s social media.
Although the Songwriter Fest has 10 great days of live music, Southwest Florida has long been a hot spot for great musical offerings, including local bars and restaurants where one can enjoy live music year-round. In Fort Myers, music lovers can check out The Ranch, The Lucky Screw, and The Bay Street Yard—to name a few. And if you’re looking for a rooftop view, try Sydney’s Rooftop, and the Firestone Skybar and Martini Bar.
Fort Myers is also home to the Fort Myers Music Walk, held on the third Friday of every month starting at 6 pm in the historic River District downtown Fort Myers—the next one being September 18. The popular event features live bands, solo artists, and street performances—playing various music genres—and it’s great fun for all ages. Plus, you can grab food and drinks from one of the many restaurants or food trucks that offer something for all…