Its funny to hear this particular trip called a "road trip" since parking in Boston is ridiculous and expensive. Public transportation can get you to all of these places easily. This is an excellent trip and I can see that you'll be taking your time in each location.

A few extra ideas to check out while on this trip is the Duck Tours and Prudential Center's Skywalk. You'll find the Duck tours in the Prudential Center at a kiosk. It is well worth the money to see the city of Boston.