ISO: Wine Recommendations

[sa_rah_cheng]

HI All -
First of all, let me state that I do not know anything about wine. However, my brother is of an amature wine enthusiast. I have this idea to give him 3 bottles of wine for his wedding along with a wine cooler. My idea is to label each for him to drink on one of his anniversaries. (i.e. one for his 1st, one for his 5th, and one for the 10th anniversary.) I'd really appreciate it if you had recommendations for wines that will be aged appropriately for each time period and are excellent wines. I'm looking to spend rought $200-$250 on the wine give or take. I am thinking that he is more of a red person than white. We were thinking maybe of a Port for the 10th anniversary?? I live in DC. Thanks so much in advance!!