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.

St. Lucia, known for its distinctive mountains, is an island that travellers dream about - a small, lush tropical gem that has volcanic beaches and fishing villages as well as luxurious resorts. The volcanic island of Saint Lucia is more mountainous than most Caribbean islands, and its dramatic twin coastal peaks, the Pitons, form the island's most famous landmark.

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.

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 Thomas is an island in the Caribbean Sea and with the islands of Saint John, Saint Croix, and Water Island a county and constituent district of the United States Virgin Islands (USVI), an unincorporated territory of the United States. Located on the island is the territorial capital and port of Charlotte Amalie. As of the 2000 census, the population of Saint Thomas was 51,181 about 47% of the US Virgin Island total. The district has a land area of 31.24 square miles (80.9 km2).

Philipsburg is the main town and capital of the country of Sint Maarten. The town is situated on a narrow stretch of land between Great Bay and the Great Salt Pond. It functions as the commercial center of Saint Martin island, whereof Sint Maarten encompasses the southern half. As of 2011, it has 1,327 inhabitants. Philipsburg also has a port that is visited by many cruise liners, ships like Celebrity Solstice, Crown Princess,Disney Magic, and since 2010, Oasis of the Seas & Anthem of the Seas.