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santo domingo
Santo Domingo

Believe it or not, I think its Hispaniola; for starters, its the first place where Columbus and company met landfall, so they established a small outpost there which later grew into a fortification, and from a fortification it grew into a town and from a town into a city. The next oldest place, is the Dominican Republic, Santo Domingo having the oldest university (I believe) in the Western Hemisphere. I could be mistaken though; its either Havana, or some other Cuban city.

You are both right, it is Santo Domingo on the Island of Hispaniola, in the Dominican Republic. Founded in 1496 by Bartholomew Columbus, the younger brother of one, Christopher Columbus.

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