Have you ever visited Portland, Maine?  I'm thing about traveling there soon for a vacation.
No but I heard it is actually a heavy dependent touring place to visit and very popular. 
I've heard that too, but I'm not sure what sites they have there.  Do you know?
Yes I learned in college that the Port of Portland is a largest tonnage seaport in New England to visit.
That's great.  So there's probably lots to do at the seaport too.
Oh absolutely Seaport is known to be the most historic and designated place so it may be full of shops and old museums etc to visit and have a great time. 
That sounds perfect!  I'm so glad you know about Portland.  Anything else of interest to see?
I try to keep up on destinations that I wish to visit and just to be prepared the population there is over a half of million so stay a few days and start early to have a great vacation.