I like Paul's (Seahawk's) suggestions about heading up the East Coast. My wife and I once made a road trip from the DC metro area up through New England and Quebec Province. That was back in '03, when we had the 95 993. We started out by going through Annapolis to Lewes, DE. Rehobeth Beach is nearby. We took the Lewes-Cape May ferry to New Jersey and went up to Long Island. We went east for a ways on Long Island, finding some twisty roads and a few small car ferries to ride on. We then took another car ferry to Connecticut and went to the Mystic Seaport. While in CT, we found a number of covered bridges that my wife wanted to see, and went to the track at Lime Rock to see some vintage racing. We looked for twisty roads to take through CT, eastern NY, and MA. I'll skip the Quebec part for now, since your plan is to go to Boston. For this trip, we spent little time on the interstates and hit a lot of small towns to get a better flavor of the area.
For the return, if you've closer to 4 weeks, I'd recommend that you leave Boston heading west, and by that I'm talking about head out to SD, WY, CO, NM, and back to TX. That's kind of what we did back in '07, when we took our 73 911E on a big road trip. Anyway, leave Boston, head west to NY and stop in at Pelican
onlycafe's restaurant in Vernon, NY (on my bucket list). He should be able to give you local knowledge on twisty roads. Watkins Glen would be great to see. You could go over to Niagra Falls, maybe cutting across Canada and coming back through SE Michigan. Or, swing back down through PA and OH, stopping in Cleveland to see the Rock & Roll Hall of Fame. On to Chicago where there's great great ethic food (I'm thinking of Polish, mmmm) and a lot of great Pelicans, too. Wisconsin has the famous Road America race track, hilly twisty country roads, tons of lakes, etc. SE Minnesota has some nice twisty roads, too. SD has the
world famous Corn Palace in Mitchell. Western SD's Badlands are very cool, and Mt. Rushmore is very nice. The Pelicans in CO should have some great recommendations on twisty roads along the front range of the Rockies.
If I get a chance, I'll try to find more specifics if desired. Road trips should be epic!
