It's great that you and your brother have similar tastes, but as Buck noted in his response, we need to have some idea of what those tastes are in order to be able to provide much in the way of specific idea. "popular sites" doesn't really give us anything to go on.

In the meantime, if you're just looking for a very broad idea of the things you could see along the way, I'd recommend checking out the RTA Map Center, which will offer you hundreds of ideas of things you could see and do along the way.