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. 

Oranjestad, known as ("Orange Town"), is the capital and largest city of Aruba. In the local language, Papiamento, Oranjestad is also often referred to simply as "Playa". The city consists of hundreds of local stores where tourists usually buy their keepsakes. The city is also home to some of the island's local residents and also many governmental buildings. Along the main "drag" (Sasakiweg street) you will find most tourist walking around and shopping and can also see the cruise ships that bring more and more external tourism into the island everyday. Close to the cruise ships is the island's largest marina where you can find great docking space for your vessel.

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Formerly the capital of the Netherlands Antilles prior to its dissolution in 2010, it has an estimated population of 150,000. Willemstad is home to the Curaçao synagogue, the oldest surviving synagogue in the Americas.

Saint Croix is an island in the Caribbean Sea, and a county and constituent district of the United States Virgin Islands (USVI), an unincorporated territory of the United States. It is the largest of the U.S. Virgin Islands, being 28 by 7 miles (45 by 11 km). However, the territory's capital, Charlotte Amalie, is located on Saint Thomas. St. Croix, like many other Caribbean islands, has tourism as one of its main sources of revenue. However, there are a number of other industries on the island to help support the economy. St. Croix was once an agricultural powerhouse in the Caribbean, but ended with the rapid industrialization of the island's economy in the 1960s. Buck Island Reef National Monument preserves a 176 acre (71 ha) island just north of Saint Croix and the surrounding reefs. This is a popular destination for snorkelers.

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.