Inspired by this thread, what’s the best place for a stereotypical American gringo to visit in Latin America? My definition of “Latin America” includes the countries of North America, Central America, South America, and the Caribbean that primarily speak a Latin-descended language, except for French speaking Canada (which is traditionally not considered the same, even if it is technically Latin). I’ll allow an answer of Puerto Rico or a place in Puerto Rico even though it is actually a US territory.
Specific suggestions of things to consider are crime rate (I’ve been told that some of the Mexican border cities are crime-infested crapholes), especially crime against tourists or random bystanders rather than organized drug smuggling gangs that live and let live unless you interfere. the extent to which locals and tourist industry workers understand English (e.g. fairly good in Puerto Rico, especially San Juan), the general attitude of locals toward gringos (e.g. warm, lukewarm, contemptuous), availability of facilities, and the overall enjoyability of the place.