Right now, the trolley companies all seem to be including a free Boston Harbor cruise when you buy a

Susan's reply : The Boston trolleys arouse lots of strong downtown seattle hotels opinions! They're a lot of fun, and a great way to see the city, especially since you can get off, explore sites in particular areas, and then get back on.
Old Town is a good choice in any case because it appears to have many more trolleys than some of the other companies (you'll see them everywhere around the city), which means you'll probably have shorter waits at the stops if you've gotten off and want to get back on.
In terms of routes and where the trolleys stop, they're similar (except for the CruisePort stop). Many of Boston's streets are very narrow, so the city provides certain places for the trolleys to stop so that they don't block traffic. There are a few other differences in routes and stops, but frankly, Boston is such a compact and walkable city that it doesn't really matter.
Right now, the trolley companies all seem to be including a free Boston Harbor cruise when you buy a trolley tour ticket. These are a lot of fun, and you get great views of the city and other sites - although since you're coming in on a cruise, you may want to skip this part!
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