Hilton Head Island, SC, United States

With a population of just 37,661, Hilton Head Island swells to over 150,000 during peak vacation season, straining its infrastructure. While the island boasts 12 miles of beachfront and an unusual amount of tree cover, the bureaucracy around development is a persistent headache - the town enforces strict zoning laws to maintain its eco-friendly image. And despite the island's rich Gullah heritage, it remains an exclusive enclave, with 70% of the land located inside gated communities. Hilton Head is best suited for retirees and the affluent seeking a carefully manicured resort town, not those seeking an authentic Lowcountry experience.