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.

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. 

Cozumel is an island in the Caribbean Sea off the eastern coast of Mexico's Yucatán Peninsula, opposite Playa del Carmen, and close to the Yucatán Channel. The island is covered with mangrove forest which has many endemic animal species. Cozumel is a flat island based on limestone, resulting in a karst topography. There are a number of visitors to the island's balnearios, scuba diving, and snorkeling. The main town on the island is San Miguel de Cozumel. The islands belongs to Cozumel Municipality of the state of Quintana Roo, Mexico.

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.

New Orleans is a major United States port and the largest city and metropolitan area in the state of Louisiana. The New Orleans metropolitan area, (New Orleans–Metairie–Kenner) has a population of 1,235,650 as of 2009, the 46th largest in the USA. The New Orleans – Metairie – Bogalusa combined statistical area has a population of 1,360,436 as of 2000. The city/parish alone has a population of 343,829 as of 2010. The city is named after Philippe d' Orléans, Duke of Orléans, Regent of France, and is well known for its distinct French Creole architecture, as well as its cross cultural and multilingual heritage. New Orleans is also famous for its cuisine, music (particularly as the birthplace of jazz), and its annual celebrations and festivals, most notably Mardi Gras. The city is often referred to as the "most unique" city in America.

Ocho Rios (Spanish for "Eight Rivers") is a town in the parish of Saint Ann on the north coast of Jamaica. Just outside the city, travelers and residents can visit Columbus Park, where Columbus supposedly first came on land, and see maritime artifacts and Spanish colonial buildings. Ocho Rios was once a fishing village but it’s now a resort with a cruise ship harbor and a busy bay beach that’s lined with hotels. Scuba diving and other water sports are offered in the town's vicinity. The name "Ocho Rios" is a misnomer because there are not eight rivers in the area. It is most likely a British corruption of the original Spanish name "Las Chorreras" ("the waterfalls"), a name given to the village because of the nearby Dunn's River Falls - (a famous waterfall and a major Caribbean tourist attraction that receives thousands of visitors each year).

George Town is a city situated on Grand Cayman island of the Cayman Islands. It serves as the capital of the Cayman Islands, in the British West Indies. As of 2007, the city had a population of 28,836, making it the second largest city (by population) of all the British Overseas Territories. George Town's famous Seven Mile Beach is a long crescent of coral-sand beach extending up to the West Bay region of Grand Cayman and is the most popular and populated area for tourists on the island.

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.