The fair place to meet is Raleigh-Durham, NC — the city closest to the midpoint of Boston and Orlando. From the farther side that’s about 12 hr 47 min of driving.
Recommended midpoint
Raleigh-Durham, NC
From Boston
12 hr 47 min
609 mi to Raleigh
From Orlando
11 hr 1 min
525 mi to Raleigh
Orlando has the shorter trip; the split is off by about 1 hr 46 min. The alternatives below can even it out. Boston and Orlando are about 1,116 miles apart.
Boston and Orlando are about 1,116 miles apart by road. Split the difference and you arrive near Raleigh, the city closest to the halfway point between them. That puts roughly 12 hr 47 min of driving on the Boston side and 11 hr 1 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. Raleigh still makes a fair, central place for Boston and Orlando to converge, splitting the travel instead of asking one side to cross the country.
If Raleigh doesn't have what you're after, Richmond and Washington are also close to the midpoint and worth a look — each keeps the drive reasonably balanced between Boston and Orlando.
Raleigh is the capital city of the U.S. state of North Carolina. It is the second-most populous city in the state, tenth most populous city in the Southeast, the largest city in the Research Triangle area, and the 39th-most populous city in the U.S. Read more →
Boston is the capital and most populous city of the U.S. state of Massachusetts. It serves as a cultural and financial center of New England, a region of the Northeastern United States. 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.