St. James City, FL

Tucked away at the southern tip of Pine Island, St. James City is a quiet, laid-back waterfront community of around 4,000 residents. Surrounded by Pine Island Sound and San Carlos Bay, the neighborhood is crisscrossed with canals that give many homeowners boat access right from their backyards. Stringfellow Road serves as the island's main artery, running north toward Matlacha and connecting you to the mainland hubs of Cape Coral and Fort Myers.

Life here revolves around the water, with working docks, local marinas, and casual seafood spots where you can pull right up in a boat. The area keeps a classic Old Florida feel, where neighbors often get around by golf cart and the pace stays unhurried. For families, younger kids attend Pine Island Elementary up the road, though the single route on and off the island means mainland commutes and errands take a bit of extra planning.