october roadtip from boston to key west

hello eveyone,
me and my girlfriend are planning to do a roadtrip this october on the east coast from boston down to key west. it will be our honeymoon, just the two of us. we will rent a convertible car, one way drop. we are planning to overnight stop in new york, richmond, charleston, jacksonville and fort lauderdale. nothing fancy about it, we want breakfast in wagon look-like cafes, sleeping in motels, meals at the sideways restaurants, see small towns and villages; this is how we (europeans) imagine an american road trip.
do you guys recommend to take highways or 2 lane maximum side ways? we are looking for something pitoresque and not industrial. on the other hand should we have any safety concerns?
thank you for replies!

Welcome aboard the RoadTrip America Forums!

If you want to see small town America, and only plan to sleep in the cities you mention and then move on, then there is really no reason to stay in, or even near, those urban areas. I have previously listed rough itineraries for two possible routes down the East Coast, and you should probably have a look at them to give you an idea of what's possible. On the one hand, you really don't have the time to devote the better part of a day to each of the cities you mention. But certainly if you have a week or so for the drive, you have plenty of time to wander the back roads and, if you or your girlfriend are good at map reading and navigating, that's just what you should do - wander. There are simply far too many roads, restaurants and motels for us to single out a select few, but you'll know the ones that meet your needs when you see them. And as for places to avoid, you'll know those too - if you feel uncomfortable, just move on.

AZBuck