On Thursday late-afternoon we attended a joint presentation, after which our son took off with his host and we went into Annapolis for dinner. The next day we took a general tour of the Yard in the morning, had lunch at Drydock and then attended another joint session in Alumni Hall followed by a tour of the engineering labs.
Same general flow this fall....
Thursday evening check-in & short info session & hand-off. Plan on a later dinner in Annapolis.
Much of Friday daytime the parents will be on campus in tours & info sessions. Free again for dinner, but much earlier.
Sat you'll be free in the morning, pickup your candidate right at lunchtime. (We chose to eat in the dry dock because the kids will not have eaten).
Either Friday or Sat AM you'll want to see the chapel & museum, which are not covered in detail normally in the tour.
It's your best chance to get a feel for USNA & cadet life. It's still not a total view into cadet life as with 200'ish visitors there much of the routine is changed. And plebe discipline is clearly relaxed for the visit.
Baltimore is close with things to see. Fort McHenry is very close to USNA and is an easy morning or afternoon visit, and there are some good seafood restaurants near there as well.
Plan on traffic getting in & out of USNA, and parking & waits can be challenging if trying to eat in downtown Annapolis, especially on the weekends. (You will be able to park on USNA for the scheduled events, just bring your letter).
If you do want to eat in downtown Annapolis, you may want to leave your car in USNA, walk out the main gate and take the trolley/shuttle around downtown. Far easier than parking if the weather is nice.
You'll have to make hotel arrangements for all but the candidate. Staying in Annapolis downtown is very high ($300-400/night at times). We found the Quality Inn ($100/night) close by on highway 50 to be a reasonable choice, and it's just 5-10 minutes away from USNA. (You'll want to use the back way to the USNA main gate). There are not many inexpensive hotel options nearby, so just be prepared.
Hope this helps!