The first thing we did was eat at an amazing restaurant called Asana. It was a Japanese restaurant at one point but is now "New England contemporary." We had foie gras, oysters, bass, seared yellowfin tuna and it was amazing. After that we took the subway to The Omni Parker House where the Boston Cream Pie was born. We paired our pie with a couple Sam Adams Boston Lagers, which was perhaps not the tastiest pairing but it was my tribute to the town I was in at the time!
The next day I had the whole day on my own to explore which I was totally up for. It rained most of the time I was out but I managed to hit up 15 of the 16 historical landmarks on the Freedom Trail (I missed Bunker Hill because of time) plus the famous Cheers bar in Beacon Hill and the Boston Public Garden complete with swan boats.