15 nights, from Miami, Florida

Miami, officially the City of Miami, is the cultural, economic and financial center of South Florida. Miami is the seat of Miami-Dade County, the most populous county in Florida. The city covers an area of about 56.6 square miles (147 km2), between the Everglades to the west and Biscayne Bay on the east; with a 2017 estimated population of 463,347, Miami is the sixth most densely populated major city in the United States. The Miami metropolitan area is home to 6.1 million people and the seventh-largest metropolitan area in the nation. Miami's metro area is the second-most populous metropolis in the southeastern United States and fourth-largest urban area in the U.S.

Miami is a major center, and a leader in finance, commerce, culture, media, entertainment, the arts, and international trade. The Miami Metropolitan Area is by far the largest urban economy in Florida and the 12th largest in the United States with a GDP of $344.9 billion as of 2017. In 2012, Miami was classified as an "Alpha−" level world city in the World Cities Study Group's inventory. In 2010, Miami ranked seventh in the United States and 33rd among global cities in terms of business activity, human capital, information exchange, cultural experience, and political engagement. In 2008, Forbes magazine ranked Miami "America's Cleanest City", for its year-round good air quality, vast green spaces, clean drinking water, clean streets, and citywide recycling programs. According to a 2009 UBS study of 73 world cities, Miami was ranked as the richest city in the United States, and the world's seventh-richest city in terms of purchasing power. Miami is nicknamed the "Capital of Latin America" and is the largest city with a Cuban-American plurality.

Greater Downtown Miami has one of the largest concentrations of international banks in the United States, and is home to many large national and international companies. The Civic Center is a major center for hospitals, research institutes, medical centers, and biotechnology industries. For more than two decades, the Port of Miami, known as the "Cruise Capital of the World", has been the number one cruise passenger port in the world. It accommodates some of the world's largest cruise ships and operations, and is the busiest port in both passenger traffic and cruise lines. Metropolitan Miami is also a major tourism hub in the southeastern U.S. for international visitors, ranking number two in the country after New York City.

Dominica, officially the Commonwealth of Dominica, is an island country in the West Indies. The capital, Roseau, is located on the western side of the island. It is part of the Windward Islands in the Lesser Antilles archipelago in the Caribbean Sea. The island is located near Guadeloupe to the northwest and Martinique to the south-southeast. Its area is 750 km2 (290 sq mi), and the highest point is Morne Diablotins, at 1,447 m (4,747 ft) in elevation. The population was 71,293 at the 2011 census. The Commonwealth of Dominica is one of the Caribbean's few republics.

The island was originally inhabited by the Kalinago and later colonised by Europeans, predominantly by the French from the 1690s to 1763. Columbus is said to have passed the island on Sunday 3 November 1493, and the island's name is derived from the Latin for "Sunday". Great Britain took possession in 1763 after the Seven Years' War, and it gradually established English as its official language. The island republic gained independence in 1978.

Its name is pronounced with emphasis on the third syllable, related to its French name of Dominique. Dominica has been nicknamed the "Nature Isle of the Caribbean" for its natural environment. It is the youngest island in the Lesser Antilles, and in fact it is still being formed by geothermal-volcanic activity, as evidenced by the world's second-largest hot spring, called Boiling Lake. The island has lush mountainous rainforests, and it is the home of many rare plants, animals, and bird species. There are xeric areas in some of the western coastal regions, but heavy rainfall occurs inland. The Sisserou parrot, also known as the imperial amazon and found only on Dominica, is the island's national bird and featured on the national flag, which is one of only two national flags containing the color purple.

Bridgetown is the capital and largest city of Barbados. Formerly The Town of Saint Michael, the Greater Bridgetown area is located within the parish of Saint Michael. Bridgetown is sometimes locally referred to as "The City", but the most common reference is simply "Town". As of 2014, its metropolitan population stands at roughly 110,000.

The Bridgetown port, found along Carlisle Bay (at 13.106°N 59.632°W) lies on the southwestern coast of the island. Parts of the Greater Bridgetown area (as roughly defined by the Ring Road Bypass or more commonly known as the ABC Highway), sit close to the borders of the neighbouring parishes Christ Church and St. James. The Grantley Adams International Airport for Barbados, is located 16 kilometres (10 mi) southeast of Bridgetown city centre, and has daily flights to major cities in the United Kingdom, United States, Canada and the Caribbean. There is no longer a local municipal government, but it is a constituency of the national Parliament. During the short-lived 1950s-1960s Federation of the British West Indian Territories, Bridgetown was one of three capital cities within the region being considered to be the Federal capital of region.

The present-day location of the city was established by English settlers in 1628; a previous settlement under the authority of Sir William Courten was at St. James Town. Bridgetown is a major West Indies tourist destination, and the city acts as an important financial, informatics, convention centre, and cruise ship port of call in the Caribbean region. On 25 June 2011, "Historic Bridgetown and its Garrison" was added as a World Heritage Site of UNESCO.

San Juan

Key West is an island and city in the Straits of Florida on the North American continent. The city lies at the southernmost end of U.S. Route 1, the longest north-south road in the United States. Key West is the southernmost city in the contiguous United States and the westernmost island connected by highway in the Florida Keys. The island is about 4 miles (6.4 km) long and 1 mile (1.6 km) wide, with a total land mass of 4.2 square miles (11 km2). Duval Street, its main street, is 1.1 miles (1.8 km) in length in its 14-block-long crossing from the Gulf of Mexico to the Straits of Florida and the Atlantic Ocean. Key West is about 95 miles (153 km) north of Cuba at their closest points.

The city is the county seat of Monroe County. The city boundaries include the island of Key West and all or part of several nearby islands: Sigsbee Park, Fleming Key, Sunset Key, and the northern part of Stock Island. The total land area of the city is 5.6 square miles (14.5 km2). Key West is the southern terminus of U.S. Route 1, State Road A1A, the East Coast Greenway and, before 1935, the Florida East Coast Railway.

Key West is 129 miles (208 km) southwest of Miami by air, about 160 miles (260 km) by car, and 106 miles (171 km) north-northeast of Havana. Key West is a port of call for many passenger cruise ships. The Key West International Airport provides airline service. Naval Air Station Key West is an important year round training site for naval aviation due to the tropical weather, which is also the reason Key West was chosen as the Winter White House of President Harry S. Truman. The central business district is located along Duval Street and includes much of the northwestern corner of the island. The official city motto is "One Human Family."

Miami, officially the City of Miami, is the cultural, economic and financial center of South Florida. Miami is the seat of Miami-Dade County, the most populous county in Florida. The city covers an area of about 56.6 square miles (147 km2), between the Everglades to the west and Biscayne Bay on the east; with a 2017 estimated population of 463,347, Miami is the sixth most densely populated major city in the United States. The Miami metropolitan area is home to 6.1 million people and the seventh-largest metropolitan area in the nation. Miami's metro area is the second-most populous metropolis in the southeastern United States and fourth-largest urban area in the U.S.

Miami is a major center, and a leader in finance, commerce, culture, media, entertainment, the arts, and international trade. The Miami Metropolitan Area is by far the largest urban economy in Florida and the 12th largest in the United States with a GDP of $344.9 billion as of 2017. In 2012, Miami was classified as an "Alpha−" level world city in the World Cities Study Group's inventory. In 2010, Miami ranked seventh in the United States and 33rd among global cities in terms of business activity, human capital, information exchange, cultural experience, and political engagement. In 2008, Forbes magazine ranked Miami "America's Cleanest City", for its year-round good air quality, vast green spaces, clean drinking water, clean streets, and citywide recycling programs. According to a 2009 UBS study of 73 world cities, Miami was ranked as the richest city in the United States, and the world's seventh-richest city in terms of purchasing power. Miami is nicknamed the "Capital of Latin America" and is the largest city with a Cuban-American plurality.

Greater Downtown Miami has one of the largest concentrations of international banks in the United States, and is home to many large national and international companies. The Civic Center is a major center for hospitals, research institutes, medical centers, and biotechnology industries. For more than two decades, the Port of Miami, known as the "Cruise Capital of the World", has been the number one cruise passenger port in the world. It accommodates some of the world's largest cruise ships and operations, and is the busiest port in both passenger traffic and cruise lines. Metropolitan Miami is also a major tourism hub in the southeastern U.S. for international visitors, ranking number two in the country after New York City.