My parents used to go on a cruise to Mexico every winter, and I think they would typically stop at Cozumel, Cancun, Samoa. However, they would NOT get off the boat when they were in Puerto Rico, because my grandfather was once stabbed by a Puerto Rican guy in Guadalcanal during the war.
This Chester kid looks exactly like the pictures my Dad took of the people who would braid my mom's hair when they got off for shore excursions. Lots of those Mexicans changed their names to American names when they came through Ellis Island, so that's probably when he switched from something like "Juan Alverez" to "Chester Brown." It makes it easier to get jobs and stuff.