Two weeks and how many miles?
How many miles are you considering? A circuit that included Boston, Florida,Montana and back to Boston would take just about the entire two weeks and wouldn't leave much time for camping or exploring.
Rule of thumb -- driving flat-out you will be unable to drive faster than an average of 50 mph over the course of eight hours of driving. So you might want to think about what is more interest to you -- covering as many miles as possible in the two weeks or having sufficient time to check out the places you are driving through.