Cape Ann, Massachusetts. Maybe I'm getting a little sentimental here, but I have so many good memories of going to Cape Ann with my family, I just had to put it on this list. If you've never heard of it, Cape Ann is like Cape Cod's less commercial, quieter and -- let's face it -- better little sister. My favorite town is called Rockport because it has beautiful beaches with an abundance of cute, little galleries and amazing hiking trails. You can stay on Wingaersheek Beach, which has the whitest, cleanest sand I've ever seen in the Northeast, for $100 per night. The beach is right near downtown Gloucester, America's oldest fishing port, which has really good restaurants and nice harbor views.