While in the Cayo Costa neighborhood, be sure to stop at Cabbage Key, where there is a popular restaurant and lodge, made famous by Jimmy Buffet's "Cheeseburger in Paradise." The main route then leads to the tiny town of Bokeelia on Pine Island. From Bokeelia, paddle east of Pine Island through Matlacha Pass Aquatic Preserve and south to the artsy fishing village of Matlacha. Beyond Matlacha lies Picnic Island and the Koreshan State Historic Site.
The romantic sounding Lovers Key / Carl E. Johnson State Park is the southern terminus of this segment. Once the possible hideout of the pirate Black Augustus, this cluster of barrier islands is the perfect place to hike, bike or land your kayak.