Boston driving requires you to be significantly more "active" that in other cities our size. It's not becuase the drivers, the speeding, or even the close-quarters that maks things difficult - it is entirely due to the complete lack of road-planning.
I makes paying attention hard because you're not sure what you are paying attention to. Biking here is the same thing, but I have mentioned that before.
Boston road workers don't do a good job when it comes to painting over fading dividers, they litteraly leave them vague which makes it hard for drivers to find an indication when they need to change lanes, etc.
A lot of strange turns and "holy shit, I didn't know I was in the wrong lane!".
You're going to want to find a garage.
Even if you find street parking, much of the city has "resident only" parking. Which means resident parking from 6PM-8AM. I'm not sure exactly which streets have these as opposed to traditional metered 2hour/1hour parking but it's worth a try and to drive around a little bit.