Roseau is the capital and largest city of Dominica. With a population of 14,847 (2001 census), it is a small and compact urban settlement, located within the Saint George parish and surrounded by the Caribbean Sea, the Roseau River and Morne Bruce. Built on the site of the ancient Kalinago Indian village of Sairi, it is the oldest and most important urban settlement on the island. It is located on the west (leeward) coast of Dominica, and is a combination of modern and colonial (French Style) architecture. Roseau is Dominica's most important port for foreign trade. Some exports include bananas, bay oil, vegetables, grapefruit, oranges and cocoa. The service sector is also a large part of the local economy.

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.

St. George's is the capital of Grenada. The town is surrounded by a hillside of an old volcano crater and is on a horseshoe-shaped harbor. St. George's is a popular Caribbean tourist destination. Founded by the French in 1650, the town has significantly developed in recent years, while preserving its history, culture, and natural beauty. The town is home of St. George’s University School of Medicine and it is also where the country's international airport is located, Maurice Bishop International Airport. It has a moderate tropical climate that ensures the success of spice production. Nutmegs are the most plentiful crop, followed by an array of such spices as cocoa, mace, cloves, vanilla, cinnamon and ginger.

The skyline of St. John's, the capital city and cruise ship port of Antigua and Barbuda, is dominated by the magnificently evocative white baroque towers of St. John's Cathedral. The towers are the first sight of Antigua for about half of the island's visitors each year, many of whom arrive by boat. The city is famous for its various shopping malls as well as boutiques throughout the city, selling designer jewellery and haute-couture clothing. There are also many independent, locally run establishments, selling a variety of fashions.

One of the major tourist areas in St. Lucia, Castries, is a port of call for cruise ships. They dock at Pointe Seraphine, to the north of the harbour, which is also a duty-free shopping centre. Beaches are also a major draw for tourists, and there are several in or very near Castries. The city doesn't have a huge amount to offer visitors, and it's usually just a place that you'll pass through on your way to the more obvious attractions of Saint Lucia - but it's worth watching those marvellous cruise ships that visit Saint Lucia dock!

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.

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. 

Philipsburg is the main town and capital of the country of Sint Maarten. The town is situated on a narrow stretch of land between Great Bay and the Great Salt Pond. It functions as the commercial center of Saint Martin island, whereof Sint Maarten encompasses the southern half. As of 2011, it has 1,327 inhabitants. Philipsburg also has a port that is visited by many cruise liners, ships like Celebrity Solstice, Crown Princess,Disney Magic, and since 2010, Oasis of the Seas & Anthem of the Seas.

Pointe-à-Pitre is the largest city of Guadeloupe, an overseas région and département of France located in the Lesser Antilles, of which it is a sous-préfecture, being the seat of the Arrondissement of Pointe-à-Pitre. Well-preserved 19th century buildings line the older streets such as Rue Achille and René-Boisneuf, and the bustling markets are a great place to soak up some local color with their tropical produce piled high, aromatic spices, and vendors dressed in flamboyant attire. One of the main tourist attractions in the city is the Place de la Victoire, a park surrounded by lovely homes and restaurants.