I don't see what's so great about Waterman's. The food costs as much as it would at a nice restaurant, and just isn't that good.

I worked at the Cavalier one summer and ate at Orion's once, I guess it was pretty good. The view's nice.

Tautog's is probably my favorite place at the oceanfront, between Atlantic and Pacific on...24th, I think? Or 23rd, I can't remember exactly. Great food, really quiet and cozy inside, not too expensive.

If you want a really nice place ($100+ for 2 people)...I haven't actually been to Steinhilber's but everyone I've talked to says it's amazing. Supposedly very upscale, classic, just a really great place. You'll pay a little more than you would at some trendy downtown Norfolk restaurant, but it's also been there since 1939 and won't be closed in ~2 years when all the hipsters take their business to the next trendy new place. It's not on the oceanfront, probably about ~15 minutes away.

From personal experience, Alexander's on the bay is really nice as well. It's in that price range, has a nice view (it's on the water), great food, definitely worth the money. If I remember, it's further down Shore drive, towards Norfolk.