My wife and I visited Boston for a long weekend in September 2014, and were trying to get as much in as we possibly could in the short time we were there. Hands down, the best decision we made was buying tickets to go on the Ye Olde Tavern Tour with Brooke.
Lucky for us, no one else happened to be taking the tour that day, so we lucked into a private tour! Brooke was very knowledgeable, laid back and fun, and we had a great time. We stopped at 3 pubs (that had historical significance) over the course of the 2.5 hour tour, and we enjoyed every minute of it. After watching people walk around with groups of 30+ with the Freedom Trail tours, we're thrilled we decided to do our historical tour this way. We have and will continue to recommend the tour to anyone traveling to Boston and looking for something fun to do in the city. My wife even bought a T-shirt online afterward. Huzzah!