Ben,
If you plan on spending some time in Boston, walk the Freedom Trail and go to Bunker Hill Monument for a great view of the city. On your way back, why don't you push it to New Orleans? It's not that far from FLA and it is definitely worth seeing. Real party city, cool people. And then you could cut through the Bayous of Louisiana and through Alabama...See if there are any French folks left down there (good luck!:-).
Je te souhaite un merveilleux premier roadtrip, tu vas adorer!
Gen