Always liked this song, I think his version is one of the best. Just a lovely tune.

One ton tamato!!
I got so tired of hearing the Sandpipers and Jose Feliciano's versions I refused to listen to it., but later, when I was stationed in Cuba at Gtmo in the mid 70s, and they still had lots of Cuban nationals working on the base every day, I learned there were lots of different verses and versions to the song, improvised almost daily. It is basically about the "girl from Guantanamo" which I thought meant from Guantanamo City, but as it was explained, it meant anyone from the poorer rural areas along the Guantanamo River, which empties of course, into Guantanamo Bay.
The English translation depends on who is singing which version, but they are all based on a farm girl from Guantanamo:
The lyrics to the song relate to a woman from Guantánamo, with whom he had a romantic relationship, and who eventually left him. The alleged real story behind these lyrics is that she did not have a romantic interest in him, but merely a platonic one. If the details are to be believed, she had brought him a steak sandwich one day as a present to the radio station where he worked. He stared at some other woman (and attempted to flirt with her) while eating the sandwich, and his friend yanked it out of his hands in disgust, cursed him and left. He never saw her again. These words are rarely sung today
Another history behind the chorus and its lyrics ("Guantanamera … / Guajira Guantanamera …") is similar: he was at a street corner with a group of friends and made a courteous pass (a polite pick-up line, like "your mother made you good" or "you came from a star", piropo in Spanish) to a woman (who also happened to be from Guantánamo) who walked by the group. She answered back rather harshly, offended by the pass. Stunned, he could not take his mind off her reaction while his friends made fun of him; later that day, sitting at a piano with his friends near him, he wrote the song's main refrain.