EMma, as somebody who has done the trip and never returned, I concur with all the advice about going by bus and train rather than hiring a car (or "renting" as they say over here. ) I had twenty-five years driving experience under my belt including driving on the wrong side of the road on the Continent before I came to the USA, and let me tell you something, driving in Boston scared me shitless. I was less scared driving in NYC during rush hour.Don't even think about driving on your own in any major USA city.
It took me at a conservative estimate, six weeks just to become comfortable, and another six before it became second nature.
That said, I hope you make the trip and that you enjoy it. Being in (very) South Florida, I probably am not much use to your itinerary, but if you do want to come down here, you will have plenty opportunities to play your music.
Murray