NAC: Adventure/Roadtrip East Coast!!!

[Steve Meyer]

It's almost time for my annual trip to New Orleans for Mardi Gras. Normally, we drive straight through from Iowa to New Orleans, but this year we thought we through in a little more adventure and start working on my goal of driving the perimeter of the U.S. So, we are flying to Boston, spending a couple nights, then flying to Myrtle Beach where we will rent a car and drive to Key West. We plan on staying in Charleston and possibly Savannah or St. Augustine and then head straight to the Keys. Then we fly from Miami to NOLA. Why do I bring this up? I know alot of you live on the East Coast and can help lead us to great little bars, restaurants and hotels. It's just me and a traveling buddy and we lean towards the hole in the wall places where you find locals and not other tourists. We don't have much of an agenda, except the flights. We arrive in Boston on Feb 14th(which did not make my wife too happy), fly to Myrtle Beach on the 16th and then fly out of
 Miami on the 20th. Any recommendations would be great. And if someone has an Audi they'd like us to drive for the trip...that'd be even better. My goal for driving the perimeter was to do it all in the same car so I could have photos of me and the Audi all over the country. Unfortunately, there is not enough time to do that this trip.
 
Thanks!
Steve