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. 

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.

Tampa is a Gulf Coast Bay city in the U.S. state of Florida. It serves as the county seat for Hillsborough County. Tampa is located on the west coast of Florida. The population of Tampa in 2000 was 303,447. According to the 2009 estimates, the city's population had grown to 343,890, making it the 54th largest city in the United States. The current location of Tampa was once inhabited by various indigenous cultures, most recently the Tocobaga. It was spotted by Spanish explorers in the early 16th century, but there were no permanent American or European settlements in the area until 1824, when the US Army established a frontier outpost called Fort Brooke at the site of today's Tampa Convention Center. The village of Tampa began as a small group of pioneers who settled near the fort for protection from the Seminole population in the area.

Santo Domingo, known officially as Santo Domingo de Guzmán, is the capital and largest city in the Dominican Republic. Its metropolitan population was 2,084,852 in 2003, and estimated at 2,253,437 in 2006. The city is located on the Caribbean Sea, at the mouth of the Ozama River. Founded by Bartholomew Columbus in 1496, it is the oldest continuously inhabited European settlement in the Americas, and was the first seat of Spanish colonial rule in the New World. It lies within the boundaries of the Distrito Nacional (D.N.; "National District"), itself bordered on three sides by Santo Domingo Province. 

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.