San Fran: America as it should be, even tempted to transfer with work to here! Ignore the rest if you can go here!
Washington: If you like your history!
New York: Busy!
Boston: Brilliant (don't bother with the cheers bar but do go a restaurant called "No Name fish Restaurant" down on the quay! and do catch a game.
Fly-drive down Highway 1: Marvelous, go southbound though so you can see the view more often. Buena vista / Santa Monica, the O.C AMAZING! and I didn't even think I'd like it, biggest sceptic ever on that one!
Might I propose alternatives like Montreal or Quebec if you don't mind a little french culture / french like cuisine mixed with BIG steak! Shorter travel time too. Vancouver's awesome too!