San Juan, officially Municipio de la Ciudad Capital San Juan Bautista (Municipality of the Capital City, Saint John the Baptist), is the capital and most populous municipality in Puerto Rico, an unincorporated territory of the United States. As of the 2000 census, it has a population of 658,304 making it the 42nd-largest city under the jurisdiction of the United States. San Juan was founded by Spanish colonists in 1521, who called it Ciudad de Puerto Rico ("Rich Port City"). Puerto Rico's capital is the second oldest European-established city in the Americas, after Santo Domingo, in the Dominican Republic. Several historical buildings are located in San Juan; among the most notable are the city's former defensive forts, Fort San Felipe del Morro and Fort San Cristóbal, and La Fortaleza, the oldest executive mansion in continuous use in the Americas. 

Roseau is the capital and largest city of Dominica. With a population of 14,847 (2001 census), it is a small and compact urban settlement, located within the Saint George parish and surrounded by the Caribbean Sea, the Roseau River and Morne Bruce. Built on the site of the ancient Kalinago Indian village of Sairi, it is the oldest and most important urban settlement on the island. It is located on the west (leeward) coast of Dominica, and is a combination of modern and colonial (French Style) architecture. Roseau is Dominica's most important port for foreign trade. Some exports include bananas, bay oil, vegetables, grapefruit, oranges and cocoa. The service sector is also a large part of the local economy.

Bridgetown is the capital and largest city of the nation of Barbados. It is the only city on Barbados and well over half the island's residents live there. It is the port of call for many cruise ships and is known for its duty-free shopping as much as for its more cultural and historical attractions.

St. George's is the capital of Grenada. The town is surrounded by a hillside of an old volcano crater and is on a horseshoe-shaped harbor. St. George's is a popular Caribbean tourist destination. Founded by the French in 1650, the town has significantly developed in recent years, while preserving its history, culture, and natural beauty. The town is home of St. George’s University School of Medicine and it is also where the country's international airport is located, Maurice Bishop International Airport. It has a moderate tropical climate that ensures the success of spice production. Nutmegs are the most plentiful crop, followed by an array of such spices as cocoa, mace, cloves, vanilla, cinnamon and ginger.