Guadeloupe (sometimes known as the ''Butterfly Island''), a French overseas territory, is an island group in the southern Caribbean Sea. It is an archipelago of nine inhabited islands, including Basse-Terre, Grande-Terre, Marie-Galante, La Desirade, Iles des Saintes, Saint-Barthélemy, Iles de la Petite Terre, and Saint-Martin (French part of the island of Saint Martin). Guadeloupe is best known for its rich culture, volcano, beautiful scenery and wonderful beaches.

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. 

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.

Kingstown is the capital, chief port, and main commercial centre of Saint Vincent and the Grenadines. With a population of 16,500 (2010), Kingstown is the most populous settlement in the country. It is the centre for the island's agricultural industry and a port of entry for tourists. The city lies within the parish of Saint George in the south-west corner of Saint Vincent.

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!

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.

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.