The freedom trail is a great way to get to know the down town of Boston, the fact that there is an actual red line marked on the floor makes it easy for anyone to follow and there are maps pretty much on every point so you can take one and know which points are you going to visit.
I have made it twice, once in summer and once in winter and both times it was fine to just walk from one point to another, it took us all day but that was our plan.
I like to start on Faneuil Hall, kind of in the middle of it, walk towards Bunkerhill, take the ferry backto Faneuil and take the rest of the tour, finishing in Boston common, that way you start and finish on main metro stations.
Tip: Right beside the USS constitution site there is a station to take the ferry, is a 10 minute ride with great views of the down town that brings you back to Faneuil hall, it completes the loop.
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