We're going on an impromptu road trip and decided to head out from Chicago towards Boston. I haven't driven this far in some time so I have some questions.

How many hours should we drive each day? We'll be taking a Chevy Trailblazer by the way.

From Boston we can either go south to New York, but we've been there many times already. How is New England and what is there to see and do?

Should we book hotels in advance or just find one when needed?

Thanks for any help. We'll be leaving around the middle of March.