I was stationed there '94-'96 as an enlisted Sailor. I thoroughly enjoyed my tour. The Mids are the nicest, hardest-working college kids I've ever seen. Annapolis is a great town to hang out in and the people are very friendly. Everyone gripes about the regs and restrictions, but I"ve never met a Mid who regretted going there.
The USNA graduates more astronauts than any other institution. Summer cruises and leatherneck training give the Mids insight into life in the Fleet. Here's the main website. The school newspaper is the Trident. It is staffed by civilians and enlisted journalists, who write about the goings on at the academy. Plebes are assigned "host" families, who take the plebes out, during their precious weekend liberty, and give them some normalcy in all that a plebe has to put up with the first year. Congratulations, on raising such a wonderful child. I hope your son gets into the academy.
I've tied up at the city docks a few times in the past and participated in a few pub crawls myself. ;-)
Thanks.