Our son visited twice; this past May (30th Company) and again in October (12th Company). It's an opportunity for candidates to (as much as they can) fully immerse in the student-life experience; without the distraction of parents. I did like the Admissions and other department presentations for parents on Friday and it was cool to meet the Superintendent too. Our son thought the boxed meal was fine and I let him know there were a few times deployed when that's what we had too. The experience of dining in King Hall our son thought was cool as well.
When they arrive, they check in, show the paperwork they were asked to bring, and then off they go. Once my son got in line, I walked from there down to Rip Miller field and watched the football team practice for a good hour- and didn't see my son again till Saturday morning. Before the visit, he was interested. After the visit he was "all-in."
If you're looking for upscale, this restaurant is right outside the visitor's gate.
The Choptank - Annapolis
110 Compromise St, Annapolis, MD 21401
However, between the visitor's gate and along Main St. towards the capitol dome, there are a bunch of nice / affordable options. We especially liked this one:
O'Brien's Oyster Bar & Seafood Tavern
113 Main St, Annapolis, MD 21401
Good luck & enjoy!