In a way it can be said that the founding of Santo Domingo was an act of desperation. Columbus’ first settlement, Villa La Navidad in present-day Haiti, was burned to the ground and all settlers killed within a year. His second settlement, La Isabela, west of present-day Puerto Plata, lasted only five years and was beset from the beginning by disease and disaster. Columbus’ brother Bartholomew, left in charge of La Isabela and facing rebellion from its disgruntled residents, pulled up stakes and moved clear around to the other side of the island. He founded Nueva Isabela on the east bank of the Río Ozama. The third time, evidently, was the charm as the city he founded, though moved to the west bank and renamed Santo Domingo, has remained the capital to this day.
That’s not to say the city hasn’t had its fair share of troubles. In 1586 the English buccaneer Sir Francis Drake captured the city and collected a ransom for its return to Spanish control. And in 1655 an English fleet commanded by William Penn attempted to take Santo Domingo but retreated after encountering heavy resistance. A century and a half later a brazen ex-slave and Haitian leader by the name of François Dominique Toussaint Louverture marched into Santo Domingo. Toussaint and his troops took control of the city without any resistance at all; the city’s inhabitants knew they were no match for the army of former slaves and wisely didn’t try to resist. During the occupation many of the city’s residents fled to Venezuela or neighboring islands. It was in Santo Domingo on February 27, 1844 that Juan Pablo Duarte – considered the father of the Dominican Republic – declared Dominican independence from Haiti, a day still celebrated today.