This is a cache about Charlie's journey. There are 2 sources of information, the song and my embellishment.
The Song:

Charlie's Song
There is also this Alternate version
(Parental advisory on the lyrics).
To remove ambiguity, you need to use the "definitive map". You will be provided this when you put the answer to this question into Certitude: Where did Charlie start his journey? (Just the first word).

You can get the definitive map by entering the correct keyword here certitude.
Note the song is from 1959, but the lyrics from 1949. The "definitive map" is from circa 1967, but it is the closest I could find so we will use that. It isn't much different than what Charlie would have encountered, though Scollay Square now has a different name. Charlie always takes the shortest route unless specified otherwise.
Assume N 51 and W 002.
Charlie handed in his dime and started the journey. The first stop was to change lines, as outlined in the song. You might think there are multiple options here, but only one fits the story, assuming he is stuck on a train going back and forth. But (start of embellishment...) Charlie accidently exited here. After he realised his mistake he re-entered the station. Charlie decided to visit Arthur Fiedler at his place of work next. He spent a couple of hours there. Charlie was starting to feel hungry, so he went to the produce market. After his snack, Charlie returned to the station, but took a different line than he arrived on. He took this line all the way to the end, which took him to where he was going in the song. But Charlie changed his mind and decided to continue to travel. His last stop before he took a nap was to a station which is no longer there, having closed on 30 April 1987, located at the intersection of Washington Street and Columbus Ave. (Charlie could also visit his cousin here).
Charlie then took a nap in a nearby park. It was time to head out again. His next stop was another station which closed on 30 April 1987. Unlike the majority of other closed stations, this one was not scrapped; instead, it was moved to the Seashore Trolley Museum in Kennebunkport, Maine in 1988, and remains there today. Next he continued north to yet another station closed in 1987. On Charlie's map this one is named after a US President. After doing some shopping at the original Filenes's Basement, Charlie headed out again. But this time he got confused. Charlie was prone to daydreaming, and he found himself deep in a daydream on the train. He woke up, not knowing where he was. The doors were open, so he exited, only to find he was still at the same station! He got in the train again, and did the exact same thing for a second time! Finally, he got on a train and it actually moved, taking him to his last stop, which was one of the many Universities in the city; this is the only one which is in a league named after a plant (that many geocachers despise). Note I didn't attend this institution, my Alma mater is on the Arborway branch of the Green Line.
This cache is part of a series of puzzle caches hidden in the same area, which I've called the Lansdown Puzzle Series. They make an "L" shape on the map. See bookmark for the complete list.
