Established as a trading post along the mangrove-lined coast south of Fort Myers, Everglades City came into its own with the creation of the Tamiami Trail. It was here that Barron Collier housed the workers who dredged their way across the wilds of cypress strands and sawgrass prairies to create the first road east-west across the wettest part of the state. It opened in 1928. The town was platted, the Everglades Rod & Gun Club opened, and a bank and City Hall established. Despite the ravages of hurricanes, many of these historic structures persist today.
This compact little town is almost at the end of the road, but Chokoluskee just south of it, the original fishing village, has that distinction. Between the two communities is the Gulf Coast Visitor Center for Everglades National Park, home to tours into the Ten Thousand Islands. Check in at Chokoluskee to find outfitters ready to send you out onto the Wilderness Waterway, a truly wild 99-mile paddle along the Everglades.
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NEARBY: Immokalee, Marco Island, Naples | ALONG: Big Cypress Swamp, Everglades National Park | PART OF: South Florida