The 11th Annual Island Hopper Songwriter Fest: September 18 – 27, 2026

 

Island Hopper Fest

11th Annual Island Hopper Songwriter Fest. Returning Sept. 18-27, 2026, the award-winning, 10-day event will include star-studded performances by some of country music’s greatest singer-songwriters from Nashville and nationwide.

It kicks off on Captiva Island Sept. 18-20 2026; moves to Cape Coral Sept. 21-22; then to downtown Fort Myers Sept. 23-24; and ends at Fort Myers Beach Sept. 25-27.

Enjoy more than 60 artists and 80 shows. Most are free in small, intimate venues.

11th Annual Island Hopper Songwriter Fest. Returning Sept. 18-27, 2026, the award-winning, 10-day event will include star-studded performances by some of country music’s greatest singer-songwriters from Nashville and nationwide.

It kicks off on Captiva Island Sept. 18-20 2026; moves to Cape Coral Sept. 21-22; then to downtown Fort Myers Sept. 23-24; and ends at Fort Myers Beach Sept. 25-27.

Enjoy more than 60 artists and 80 shows. Most are free in small, intimate venues.

View a short video of last year’s Island Hopper Songwriter Fest: Link to video.

Island Hopper Tram

Hop on the Trolley… and Go. Stay at the Captiva Island Inn and enjoy FREE Transportation Around Captiva During Songwriter’s Fest on Captiva Island

The free hop-on, hop-off tram will run the festival route, with stops at South Seas, along Andy Rosse Lane and ‘Tween Waters Inn & Marina during the following times:

Friday, Sept. 18, 3pm – 10pm
Saturday, Sept. 19, 1:00pm – 10:00pm
Sunday, Sept. 20, 1:00pm – 6:00pm

Please Note: Uber/Lyft services are unavailable on the island. There are local transportation services, such as Sanibel Taxi, Sanibel Double D, and Majestic Transportation Services.

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1, 2 & 3 Bedroom Suites

Captiva Island 5-Bedroom Home Vacation Rentals