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. 

New York City is the most populous city in the United States and the center of the New York metropolitan area. The city has a significant impact on global commerce, finance, media, culture, art, fashion, research, education, and entertainment. As host of the United Nations Headquarters, it is also an important center for international affairs. The city is often referred to as ''New York City'' or the ''City of New York'', to distinguish it from the state of New York, of which it is a part. Located on a large natural harbor on the Atlantic coast of the Northeastern United States, New York City consists of five boroughs: The Bronx, Brooklyn, Manhattan, Queens, and Staten Island. 

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.

Tortola is the largest and most populated of the British Virgin Islands, a group of islands that form part of the archipelago of the Virgin Islands. It has a surface area of 55 square kilometres (21 square miles) with a total population of 23,908, with 9400 residents in Road Town. Mount Sage is its highest point at 530 metres (1,740 feet) above sea level. It features several white-sand beaches, including Cane Garden Bay and Smuggler’s Cove.

Charlotte Amalie, located on St. Thomas, is the capital and largest city of the U.S. Virgin Islands. Founded in 1666 as Taphus (meaning "beer houses" or "beer halls"), the town has been inhabited for centuries. Hundreds of ferries and yachts pass through town each week, and at times the population more than doubles. The city is known for its Danish colonial architecture, building structure and history, and a dozen streets and places throughout the city have Danish names. Charlotte Amalie has buildings of historical importance including St. Thomas Synagogue, the second-oldest synagogue in the Western Hemisphere, and Frederick Lutheran Church, the oldest Lutheran church in the Western Hemisphere. The town has a long history of pirates, especially stories of Bluebeard and Blackbeard (Edward Teach). In the 17th century, the Danes built both Blackbeard's Castle and Bluebeard's Castle attributed to the pirates. Blackbeard's Castle is a U.S.National Historic Landmark. Another tourist attraction is Fort Christian, the oldest standing structure in the Virgin Islands Archipelago. A copy of the Liberty Bell is in Emancipation Park, which is a tourist attraction.

Basse-Terre Island is the name of the western-half of Guadeloupe proper, in the Lesser Antilles. Despite its name, Basse-Terre Island (literally "Low Land" Island, "Down Land" Island) is the highest island of Guadeloupe, rising to 1,467 metres (4,813 feet) above sea level at the Soufrière volcano. Above the city of Basse-Terre on a mountain road, is the village of Saint-Claude, at the base of the Soufrière volcano. The village is noted for its coffee and banana plantations & stately homes. Tours to ascend the Soufrière can be arranged. A few beaches are located along the coast, north and south of the city of Basse-Terre. There are also fishing areas.