I'll never forget my first bus ride in Boston: going through a tunnel that suddenly narrowed by 1 lane deep underground, driving 2km past our next stop to reach a u-turn to the other side of the highway.. It has the craziest road infrastructure I have ever seen.
Although Boston driving can still be a bit crazy in areas you're not accustomed to, the combination of the Big Dig and GPS has taken some of the rougher edges off, especially for the main highways and getting to and from the airport.