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. 

Oranjestad, known as ("Orange Town"), is the capital and largest city of Aruba. In the local language, Papiamento, Oranjestad is also often referred to simply as "Playa". The city consists of hundreds of local stores where tourists usually buy their keepsakes. The city is also home to some of the island's local residents and also many governmental buildings. Along the main "drag" (Sasakiweg street) you will find most tourist walking around and shopping and can also see the cruise ships that bring more and more external tourism into the island everyday. Close to the cruise ships is the island's largest marina where you can find great docking space for your vessel.

St. Lucia, known for its distinctive mountains, is an island that travellers dream about - a small, lush tropical gem that has volcanic beaches and fishing villages as well as luxurious resorts. The volcanic island of Saint Lucia is more mountainous than most Caribbean islands, and its dramatic twin coastal peaks, the Pitons, form the island's most famous landmark.

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.

Saint Kitts and Nevis are a pair of tropical islands in the Caribbean and the smallest sovereign state in the Americas, in both area and population. The country is a Commonwealth realm, with the British Monarch (currently, Elizabeth II) as its head of state.  Saint Kitts and Nevis were among the first islands in the Caribbean to be settled by Europeans. It was home to the first British and French colonies in the Caribbean, and thus has also been titled "The Mother Colony of the West Indies''. The natural aspect is what makes the country remarkable. Many tropical birds which one rarely finds elsewhere are present in great concentration in the nature and there are also the famous monkeys which, it is said, were introduced by the pirates      

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Formerly the capital of the Netherlands Antilles prior to its dissolution in 2010, it has an estimated population of 150,000. Willemstad is home to the Curaçao synagogue, the oldest surviving synagogue in the Americas.

Saint Thomas is an island in the Caribbean Sea and with the islands of Saint John, Saint Croix, and Water Island a county and constituent district of the United States Virgin Islands (USVI), an unincorporated territory of the United States. Located on the island is the territorial capital and port of Charlotte Amalie. As of the 2000 census, the population of Saint Thomas was 51,181 about 47% of the US Virgin Island total. The district has a land area of 31.24 square miles (80.9 km2).

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. 

Great Stirrup Cay is a small island that is part of the Berry Islands in the Bahamas. Norwegian Cruise Line purchased the island from the Belcher Oil Company in 1977 and developed it into a private island for their cruise ship passengers. The northern part of the island has a sandy beach surrounded by rocks with snorkeling areas. The southern part features a helicopter airfield (with a sign reading "Great Stirrup Cay International Airport"), a large area without vegetation, and numerous concrete blocks. These are all remnants of a previous U.S. military installation and satellite tracking station. The island's lighthouse was originally constructed in 1863 by the Imperial Lighthouse Service. Great Stirrup Cay is adjacent to Little Stirrup Cay, Royal Caribbean Cruises' private island.