I know the area very well... at least I did. I worked for nearly a decade at the local newspaper, The Virginian-Pilot. I was downsized at the beginning of 2012, so some of what I tell you may be outdated.
Chesapeake has a couple of decent malls, Greenbrier and Chesapeake Square. Chesapeake itself doesn’t really have a downtown per se... it’s more like a suburb of Norfolk. Downtown Norfolk also has a very nice mall downtown, the MacArthur Center, along with some great dining and nightlife options. If I remember correctly, Granby street is the heart of downtown shopping.
The MacArthur Memorial is in Norfolk, as is the USS Wisconsin and an adjoining maritime museum. The Chrysler Museum of Art is very nice. Ghent is their kind of bohemian neighborhood with some really nice restaurants there too.
Across the water from Norfolk (there’s a ferry) is Portsmouth. Portsmouth was always a little rough around the edges, but was making great strides in rejuvenation. I’d be interested to know how that turned out. Portsmouth has a children’s museum and a couple more museums.
Virginia Beach of course has the oceanfront and a number of nice restaurants on the waterfront. But it’s lacking in tourist things like amusement parks you’ll find in other major beach destinations.
Lots of great festivals in the late summer in fall, like the Pungo Strawberry Festival in the outskirts of Va Beach. The Suffolk Peanut Fest. You get the point.
Busch Gardens and Colonial Williamsburg is less than an hour away from much of Chesapeake. DC is about three hours due north, so great for a weekend getaway. Charlottesville and Monticello are a couple of hours away. The Outer Banks of NC a couple of hours. The Wright Brothers Memorial... Roanoke Island (Lost Colony outdoor drama). Lighthouses.
The Eastern Shore is right across the Chesapeake Bay Bridge Tunnel from Va Beach. THAT is a nice quick getaway from the hustle and bustle, quite a few nice B&Bs and eateries. Antiquing.
Hampton has the Air and Space Museum, and if you’ve seen the movie Hidden Figures, Hampton is where all that happened.
Norfolk has a zoo, and Va Beach a nice aquarium. I did the annual Discover Hampton Roads magazine for the pilot for several years. Let me know if you have any follow-up questions.
Those two pages are very outdated, so disregard any specific special events and whatnot. Sorry. Pilotonline.com still seems to be a pretty good source of information... but the website itself has always been awful and still is.