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. 

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.

Key West is an island in the Straits of Florida on the North American continent at the southernmost tip of the Florida Keys. It is considered the southernmost city in the continental United States. The city also occupies nearby islands and portions of nearby islands. It’s popularly known for its stunning beaches, coral reefs – destinations for diving and snorkeling.

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.