Nine Cities of the Caribbean and Central America in Order of Founding

Founded in 1495, it claims to be the first Santiago established in the Americas. An earthquake destroyed the original settlement and the city was rebuilt at its current site in 1506. It is the Dominican Republic's second-largest city, with 771,748 people in 2022, and the Cibao region it anchors produced 33 percent of national GDP that year.

Founded by Spanish colonists in 1521, San Juan is the second-oldest European-founded capital city in the Americas after Santo Domingo. Its historic fortifications and La Fortaleza, the oldest executive mansion in continuous use in the Americas, are UNESCO World Heritage sites.

The city predates the Spanish conquest of 1524 by more than 300 years. It lies in a volcanic basin at 2,330 meters, and from 1838 to 1840 it was capital of the short-lived state of Los Altos within the Federal Republic of Central America. It had 180,706 people at the 2018 census.

Founded in 1524 by Francisco Hernández de Córdoba, the original city was abandoned in 1610 after eruptions and earthquakes, and its ruins at León Viejo became a World Heritage Site in 2000. León was Nicaragua's capital until the seat moved to Managua in 1852, and its university, founded in 1812, is Central America's second oldest.

Pedro de Alvarado founded the city on June 27, 1536. It declined for much of the colonial period and revived in the late 1800s through banana cultivation and railroad building. It is the largest city in Central America that is not a national capital, and in 2011 it generated about two-thirds of Honduras's GDP.

The Dutch West India Company took Curaçao from Spain in 1634, and the walled quarter of Punda was established that year. The historic center earned UNESCO World Heritage status in 1997, and the city holds the oldest surviving synagogue in the Americas, built in 1674.

Governor Jacques Dyel du Parquet established a fort here in 1639, and the town took its present name in 1807 after being known as Fort-Royal. It became Martinique's leading city after the 1902 eruption of Mount Pelée destroyed the rival city of Saint-Pierre.

Founded in 1666 as Taphus, Danish for beer house, it was renamed in 1691 for Charlotte Amalie of Hesse-Kassel, queen consort of Denmark and Norway. Its harbor, once a haven for pirates including Blackbeard, now draws about 1.5 million cruise passengers a year, and it is the only United States capital where traffic drives on the left.

Founded around 1796, it is known locally as Playa, Papiamento for beach, and takes its official name from the Dutch House of Orange. It grew from a trading settlement on Paardenbaai into Aruba's hub for tourism, shipping and commerce, with 28,658 people at the 2020 census.