Are you traveling with small children or animals and need to make frequent stops? Will you be stopping at historical and other interesting sights on the way? (You'll be passing a lot of them!) Is there only one driver? Will you stop overnight?

You'll be traveling about 1800 miles. With two drivers and only a few stops (gas, food, bathroom) on expressways, you could do this in two days, but someone will have to pry your hands off the steering wheel when you get to Medford.