The fair place to meet is Charlotte, NC — the city closest to the midpoint of Cleveland and Orlando. From the farther side that’s about 9 hr 43 min of driving.
Recommended midpoint
Charlotte, NC
From Cleveland
9 hr 8 min
436 mi to Charlotte
From Orlando
9 hr 43 min
463 mi to Charlotte
Cleveland has the shorter trip; the split is off by about 35 min. The alternatives below can even it out. Cleveland and Orlando are about 896 miles apart.
Cleveland and Orlando are about 896 miles apart by road. Split the difference and you arrive near Charlotte, the city closest to the halfway point between them. That puts roughly 9 hr 8 min of driving on the Cleveland side and 9 hr 43 min on the Orlando side — the fairest single meeting point among the cities near the middle.
Over this distance most people will fly rather than drive the whole way. Charlotte still makes a fair, central place for Cleveland and Orlando to converge, splitting the travel instead of asking one side to cross the country.
If Charlotte doesn't have what you're after, Raleigh and Atlanta are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Cleveland and Orlando.
Charlotte is the most populous city in the U.S. state of North Carolina. With a population of 874,579 at the 2020 census, it is the 14th-most populous city in the U.S., seventh-most populous city in the South, and second-most populous city in the Southeast. Read more →
Cleveland is a city in the U.S. state of Ohio and the county seat of Cuyahoga County. Located along the southern shore of Lake Erie, it is situated across the lake from Ontario, Canada, and is approximately 60 miles west of the Ohio–Pennsylvania state line. Read more →
Orlando is a city in and the county seat of Orange County, Florida, United States. Part of Central Florida, it is the fourth-most populous city in the state and its most populous inland city, with a population of 307,573 at the 2020 census. Read more →
City descriptions adapted from Wikipedia (CC BY-SA); photos via Wikimedia Commons, credited above.
Estimates use straight-line distance and typical road speeds; real drive times vary with route and traffic.