Boston is the capital of and largest city in Massachusetts, and is one of the oldest cities in the United States. The largest city in New England, Boston is regarded as the unofficial "Capital of New England" for its economic and cultural impact on the entire "New England" region. The city proper had a 2009 estimated population of 645,169, making it the twentieth largest in the country. It is also the anchor of a substantially larger metropolitan area called  "Greater Boston", home to 4.5 million people and the tenth-largest metropolitan area in the country. Greater Boston as a commuting region includes six Massachusetts counties:  "Essex", "Middlesex","Norfolk", "Suffolk", "Plymouth", "Worcester", northern "Bristol" County, all of "Rhode Island" and parts of "New Hampshire"; it is home to 7.6 million people, making it the fifth-largest Combined Statistical Area in the United States.

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. 

Roatán is one of the Honduras Bay Islands in the Caribbean Sea. The island was formerly known as Ruatan and Rattan. Rests on an exposed ancient coral reef, with two cruise ship ports, Roatan has become a cruise destination, and roads and beaches can be busy when ships are in port. The western side of the island is the most populated and where most tourists stay, and the eastern side is more remote and isolated. Roatan has a warm climate with daytime temperatures between 80-90 year round.

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.

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.

Tortola is the largest and most populated of the British Virgin Islands, a group of islands that form part of the archipelago of the Virgin Islands. It has a surface area of 55 square kilometres (21 square miles) with a total population of 23,908, with 9400 residents in Road Town. Mount Sage is its highest point at 530 metres (1,740 feet) above sea level. It features several white-sand beaches, including Cane Garden Bay and Smuggler’s Cove.

Cartagena is Colombia's most famous tourist destination on the Caribbean coast. The city is renowned for its colonial and colourful architecture. With a tropical climate, the city is also a popular beach destination. The city was founded on June 1, 1533, and named after Cartagena, Spain, itself after the original Carthage in Tunisia. However, settlement in this region around Cartagena Bay by various indigenous people dates back to 4000 BC. During the colonial period Cartagena served a key role in administration and expansion of the Spanish empire. It was a center of political and economic activity due to the presence of royalty and wealthy viceroys. In 1984 Cartagena's colonial walled city and fortress were designated a UNESCO World Heritage Site.