Hey Bryan,
Born and raised in the area, currently living in Portsmouth. Welcome and hope you enjoy your stay. Emerson's is the best place in Hampton Roads, IMHO. They have a few locations including Hampton, Norfolk, Chesapeake and VA Beach. Just google Emerson's cigars for all the info you need. My local spot is the Emerson's in Greenbriar. I know pretty much all the guys over there and they are extremely good people. Pipes and pipe tobacco selection are sub par but not terrible. They have a nice smoking lounge area with 6 or 7 comfortable leather chairs and 2 flatscreens as well as 2 separate tables with 3 or 4 chairs around each. Also a kitchen type area with sink and all and a Coke vending machine. WONDERFUL selection of cigars as well, they got that covered. There is another shop in Suffolk called Bond's, but I'm not a big fan of the customer service there and their pipe and pipe tobacco selection suck so they do not get my business. The owner had some type of issue with Padron and they don't even carry their cigars in the store....that's a deal breaker right there for me.
Hope this helps!