geezer
Colonel, USAF (Retired)
Anyone have experience road tripping through New England? ...Then back towards the coast and into Boston for a day or two before heading home.
I lived in New England (Rhode Island to be specific) for a while. Here are some recommendations for your time in Boston.
Start off by taking one of the "Hop-on-Hop-off" Trolley tours. It will give you an overview of the city (mostly historical sites). If you see something you want to explore for a while, you can "hop off" for a while, then "hop on" a subsequent bus.
https://www.tripadvisor.com/Attraction_Products-g60745-zfc12058-zfg11873-Boston_Massachusetts.html
Walk the Freedom Trail. It's a 2.5 mile trail marked by a red line on the sidewalks/streets. It will take you by 17 historic sites.
http://thefreedomtrail.org/freedom-trail/
Have lunch at the Cheers bar. Yes, it's touristy, but the food is actually quite good.
https://cheersboston.com/
After lunch, walk through the Boston Common--the original home of free speech and public assembly. You'll see/hear folks making speeches on all sorts of topics. It's America's original "general board."
https://www.boston.gov/parks/boston-common
Drive south and visit the John F. Kennedy Presidential Library. Not as big as most modern presidential libraries, but still worth the time.
https://www.jfklibrary.org/
You can keep driving south on Rt 3 (Southeast Expressway) and see Plymouth Rock.
If I was doing the trip, I would spend less time in NY, Maine, NH and western Mass to allow a trip to Cape Cod (drive all the way to the end at Provincetown), and then south to Newport, Rhode Island to take a sailboat ride and visit mansion row.
https://www.capecodchamber.org/
https://www.discovernewport.org/
What to eat in Boston: clam chowder and lobster rolls. You can also get both at roadside stands on Rt 3.