Santo Domingo  was named a UNESCO World Cultural Heritage Site in 1990. Its history is both glorious and sad. While it has so many bragging rights as the City of Firsts, those firsts came at a very high price during different periods of time in this city’s many centuries of existence. Many lives were lost (Taíno mostly) to pave the way for the city to be built and prosper.
Santo Domingo is the result of many failed attempts at settlement. Columbus couldn’t catch a break. His first settlement at La Navidad was annihilated. When Christopher was away in Spain, the second try, La Isabela , which was just west of Puerto Plata , fell to yellow fever and mutiny while under the care of his brother, Bartolomé. Bartolomé then set up the third settlement, Nueva Isabela, on the eastern bank of the Río Ozama. Although it was thriving, it was eventually leveled by a hurricane.
Finally, with the help of his governor, he founded Santo Domingo de Guzmán  (the city’s official name), an 11-block area on the western bank of the Río Ozama. And it began to thrive. At the same time, the brutalization of the Taíno natives raged on with forced labor.
Santo Domingo began to weaken, and pirates were catching wind of its vulnerability. In 1586, Sir Francis Drake, the English buccaneer, came to town and seized it for a month until he finally got the Spanish to pay him a ransom to get it back.
He wasn’t the last to try to take Santo Domingo, either. William Penn of England tried, and former slave François Dominique Toussaint L’Ouverture of Haiti succeeded until February 27, 1844, when Juan Pablo Duarte finally won independence for the Dominican Republic  after a series of rapid-succession occupations by the French (1802 and 1804), the British (1803 and 1809), the Spanish (1809), and finally the Haitians in 1822—all of which happened in the Ciudad Colonial .