As an upperclassman, yes. My DD already has leave approved for her brother's wedding in September. As a Plebe, it is much more difficult, but maybe. It depends on the company. Have your DS talk to his CC (Company Commander.) Not the one from INDOC, but his company once the academies year starts as soon as possible. It will help if your DS is totally squared away on everything else. It will be tough so early during Plebe year, difficult to impossible during sea year, and don't even get me started on what he will miss if he goes active duty. You can pm me for more info.