Born and raised in Hampton Roads!!
I’ve lived in Chesapeake (specifically Western Branch area), Suffolk (specifically HarbourView area), Norfolk (at ODU), and now Newport News (Denbigh srea, right up there by Williamsburg). I’ve always enjoyed the area.
There’s definitely more to do in the Va Beach area, but it is more congested. I hate traffic so I avoid VB. But if you don’t mind it too much, VB is a great place to live. Housing prices differ depending on the area. Some are crazy expensive, some are moderate, and some are low (the iffy areas)
Chesapeake is nice. It’s big so there’s big differences in the areas. Greenbier is more city like. Hickory and Great Bridge are more country like. Western Branch is a good mix of the two and is high demand for families (so is Hickory or Great Bridge). I grew up in Western Branch and loved it. Most places in Chesapeake have the same price ranges for houses.
I’m not a fan of Norfolk. I lived there for 4 years when I was at ODU but I happy to leave. Most areas aren’t ideal and the ones that are, are pretty pricey. There’s tons of traffic due to Naval Station Norfolk. The downtown areas are fun for going out though.
Suffolk is nice if you can afford the nice areas. Unfortunately downtown (old) Suffolk is no longer a “nice” area, even though the houses are gorgeous and historical. Harbour View is great, but pricey.
Peninsula (Newport News, Hampton, Williamsburg, Yorktown)
Newport News is nice in the right areas. Denbigh, Oyster Point, parts of J Clyde and Warwick are good. Fair housing prices as well. If you like the outdoors Newport News park (Deer Run) is nice and has a lot of things to do. Nightlife wise, not much in NN.
Hampton has it’s nice areas too. I’m not super familiar with them though. I do know that the 23666 area code is nice. There are a few popular bars/night clubs in Hampton.
Williamsburg is very nice. All of it. But that is reflected in the housing prices. They are higher. There are tons of things to do though. Great shopping, historical sites, winery, and it’s pretty close to Richmond. Oh, there’s also Busch Gardens and Water Country USA.
Yorktown is similar to Williamsburg. I’m not super familiar with it, but I do know that it’s very nice.
That’s about all I have for starters. If you have any specific questions for any area just let me know and I’ll try to answer it as best as possible 🙂