Orlando was a small county seat and citrus town, laid out around a courthouse in 1857, until 1965, when Walt Disney announced a park southwest of it. Its name probably comes from a Shakespeare play and not from a soldier called Orlando Reeves, the story the town told for a century. Magic Kingdom opened in 1971, and Orlando became the fourth most visited city in the United States after New York, Miami and Los Angeles. The other thing that shaped it is the coast to the east: Cape Canaveral and the Kennedy Space Center are about 50 miles away, which is why a lot of the region works in aerospace.
The city has two faces and most visitors only meet one. The first is the theme parks, which are enormous, expensive and, on the wrong day, mostly queues. The second is a mid-sized Southern city with a lake downtown, a Vietnamese district on Colonial Drive, a college town called Winter Park with the biggest collection of Tiffany glass anywhere, and springs where the water stays cool and clear. Five days is the right length because you can have both: one day at Kennedy Space Center, one day in a single park, and three days of the Orlando that locals actually use. You do need a car for most of it, and we say so plainly below.
The plan is organized by place, not by ride. Day one is downtown Orlando, Lake Eola and Mills 50, day two is Winter Park, day three is a full day at the Kennedy Space Center Visitor Complex, day four is Magic Kingdom, and day five is a spring, a museum and dinner in a neighborhood. We recommend starting on a Monday: the Morse Museum is closed Mondays, so day two lands on a Tuesday, Magic Kingdom falls on a Thursday when the crowds are thinner than at weekends, and the springs are quieter on a Friday than on a Saturday. For the rest of the country, see our guide to the United States.