St. John's is the capital and largest city in Newfoundland and Labrador, Canada. St. John's was incorporated as a city in 1888, yet is considered by some to be the oldest English-founded city in North America. Situated on the eastern tip of the Avalon Peninsula on the island of Newfoundland, it is one of the world's top ten oceanside destinations. Its name has been attributed to the feast day of John the Baptist, when John Cabot was believed to have sailed into the harbour in 1497, and also to a Basque fishing town with the same name.

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.

Miami is a major city located on the Atlantic coast in southeastern Florida and the county seat of Miami-Dade County, the most populous county in Florida and the eighth-most populous county in the United States with a population of 2,500,625. The 42nd largest city in the United States, with a population of 433,136, it is the principal, central, and most populous city of the South {Florida} metropolitan area, the most populous metropolis in the Southeastern United States. According to the US Census Bureau, Miami's metro area is the seventh most populous in the United States, with an estimated population of 5,547,051 in 2009. 

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. 

Gustavia, St Barts' red-roofed capital, is a small harbor town lined with chic boutiques, duty free shops, gourmet restaurants, and galleries. It is the main town of the island of Saint Barthélemy (also known as St. Barts). It was named after King Gustav III of Sweden. St. Barts was a French possession originally, and the area was called Carenage after the shelter it provided to damaged ships. Gustavia was founded after Sweden bought the island from France in 1785. The island was sold back to France in 1878.  For beautiful sightseeing views, visit Fort Gustav (the most important fort during the Swedish period), or head to the top of the 29 m hill for vistas of Shell Beach amid the few remaining stonewalls of Fort Karl!