Nassau - an attractive harbour, a colourful blend of old world and colonial architecture, and a busy port, is the capital and largest city of The Bahamas. The tropical climate and natural beauty of the Bahamas have made the city a popular tourist destination. Nassau is considered a historical stronghold of pirates.

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. 

Havana, officially Ciudad de La Habana, is the capital city, major port, and leading commercial centre of Cuba. The city is one of the 15 Cuban provinces. The city/province has 2.1 million inhabitants, the largest city in Cuba and the second largest in the Caribbean region, after Santo Domingo. The city extends mostly westward and southward from the bay, which is entered through a narrow inlet and which divides into three main harbours: Marimelena, Guanabacoa, and Atarés. The sluggish Almendares River traverses the city from south to north, entering the Straits of Florida a few miles west of the bay.

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.

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. 

Santiago de Cuba is the capital of the Santiago de Cuba province in south-eastern Cuba. Historically Santiago de Cuba has long been the second most important city on the island after Havana, and still remains the second largest. It is on a bay connected to the Caribbean Sea and is an important sea port. The city best known for colonial architecture and revolutionary history.

Cienfuegos is a stunning waterfront city situated on the southern coast of Cuba. Its picturesque nautical setting has earned it the title, “the Pearl of the South”, a description that has endured for centuries.  The history of Cienfuegos possesses interesting antecedents and is rich in aborigine and Hispanic legends. Founded in 1819, it's one of Cuba's newest settlements, but also one of its most architecturally interesting, a factor that earned it a Unesco World Heritage Site listing in 2005.

Port Antonio is the capital of the parish of Portland on the northeastern coast of Jamaica, about 60 miles (100 km) from Kingston. It is the island's third largest port, famous as a shipping point for bananas and coconuts, as well as one of its most important tourist attractions, tourism being a major contributor to the town’s economy.