We’ll ease in around the Naples / Ft. Myers area with Gulf Coast sunshine, beach walks, waterfront dinners, patio drinks, and a softer landing before the Key West chaos begins. This is the warm-up lap: pretty, relaxed, coastal, and just fancy enough to pretend we’re behaving.
From there, the road trip portion starts earning its keep. Think Everglades edges, big-sky Florida weirdness, roadside stops, swampy scenery, “should we pull over for that?” moments, and the slow build from mainland Florida into island mode. Then comes the drive down the Overseas Highway — the kind of route where the road starts feeling less like transportation and more like a dare — with the Seven Mile Bridge doing exactly what it came to do: make everyone stare out the window and question why they live anywhere with snow.