Old Point Comfort is a point of land located in the independent city of Hampton, Virginia. Previously known as Point Comfort, it lies at the extreme tip of the Virginia Peninsula at the mouth of Hampton Roads in the United States. It was renamed Old Point Comfort to differentiate it from New Point Comfort 21 miles (34 km) up the Chesapeake Bay. A group of enslaved Africans was brought to colonial Virginia at this point in 1619. Today the location is home to Continental Park and Fort Monroe National Monument.

Norfolk is an independent city in Virginia, United States. As of the 2020 census, Norfolk had a population of 238,005, making it the third-most populous city in Virginia after neighboring Virginia Beach and Chesapeake, and the 96th-most populous city in the nation. Norfolk holds a strategic position as the historical, urban, financial, and cultural center of the Hampton Roads region (sometimes called "Tidewater"), which has more than 1.8 million inhabitants and is the 37th-largest metropolitan area in the U.S., with ten cities.

Jacksonville is the most populous city proper in the U.S. state of Florida, located on the Atlantic coast of northeastern Florida. It is the seat of Duval County, with which the City of Jacksonville consolidated in 1968. It was the largest city by area in the contiguous United States as of 2020, and became the 10th largest city by population in 2023. 

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Rum Cay (formerly known as Mamana and Santa Maria de la Concepción) is an island and district of the Bahamas. It measures 30 square miles (78 km2) in area, it is located at Lat.: N23 42' 30" - Long.: W 74 50' 00". It has many rolling hills that rise to about 120 feet (37 m). 

The island is believed to have acquired its modern name from a shipwrecked cargo of rum. The main settlement is Port Nelson. Its population was recorded as 90 as of 2022. Before 1996 the island was part of a combined district of San Salvador and Rum Cay.

The Castillo de San Pedro de la Roca (also known by the less formal title of Castillo del Morro or as San Pedro de la Roca Castle) is a fortress on the coast of the Cuban city of Santiago de Cuba. About 6 miles (10 km) southwest of the city centre, it overlooks the bay. The fortress was declared a World Heritage Site by UNESCO in 1997, cited as the best preserved and most complete example of Spanish-American military architecture.

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Historically Santiago de Cuba was the second-most important city on the island after Havana, and remains the second-largest. It is on a bay connected to the Caribbean Sea and an important sea port. In the 2022, the city of Santiago de Cuba recorded a population of 507,167 people.

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Golden Grove is 10 kilometres (6.2 mi) northeast of Port Morant and 11 kilometres (6.8 mi) east of Bath. The banana-handling port, Port Morant, is located in Bowden, Golden Grove. A path starting from Golden Grove leads to the 100 foot (30 m)-tall Morant Point lighthouse cast in London, England in 1841. According to a 2009 census, Golden Grove had a population of 3,057.

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Kingston is the capital and largest city of Jamaica, located on the southeastern coast of the island. It faces a natural harbour protected by the Palisadoes, a long sand spit which connects the town of Port Royal and the Norman Manley International Airport to the rest of the island. Kingston is the largest English-speaking city south of the United States in the Western Hemisphere.

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Havana was founded by the Spanish in the 16th century. It served as a springboard for the Spanish conquest of the Americas, becoming a stopping point for Spanish galleons returning to Spain. King Philip III of Spain granted Havana the title of capital in 1607. Walls and forts were built to protect the city. The city is the seat of the Cuban government and various ministries, and headquarters of businesses and over 100 diplomatic offices.

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Paradise Island is an island in the Bahamas formerly known as Hog Island. The island, with an area of 277 hectares (685 acres) (2.8 km2/1.1 sq mi), is located just off the shore of the city of Nassau, which is itself located on the northern edge of the island of New Providence.

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