If you want to stay in the US, I say DC. If you want to stay fairly sheltered, go to Vancouver or Montreal.
If you feel a bit more adventurous, Singapore. It's an easy first step to traveling in Asia because you get the awesome food (Malaysian) but everyone speaks English (literally--it's one of the national languages), it's modern, safe, and clean. Just don't chew gum. Or even bring gum into the country.