14 nights Miami, Philipsburg, St John s, Bridgetown, Funchal, Lisbon

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.

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.

Madeira, officially the Autonomous Region of Madeira, is one of the two autonomous regions of Portugal (along with the Azores). It is an archipelago situated in the north Atlantic Ocean, southwest of Portugal. Its total population was estimated in 2011 at 267,785. The capital of Madeira is Funchal, which is located on the main island's south coast.

The archipelago is just under 400 kilometres (250 mi) north of Tenerife, Canary Islands. Bermuda and Madeira, a few time zones apart, are the only land in the Atlantic on the 32nd parallel north. It includes the islands of Madeira, Porto Santo, and the Desertas, administered together with the separate archipelago of the Savage Islands. The region has political and administrative autonomy through the Administrative Political Statue of the Autonomous Region of Madeiraprovided for in the Portuguese Constitution. The autonomous region is an integral part of the European Union as an outermost region.

Lisbon is the capital and the largest city of Portugal, with an estimated population of 505,526 within its administrative limits in an area of 100.05 km2. Its urban area extends beyond the city's administrative limits with a population of around 2.8 million people, being the 11th-most populous urban area in the European Union. About 3 million people live in the Lisbon Metropolitan Area (which represents approximately 27% of the country's population). It is mainland Europe's westernmost capital city and the only one along the Atlantic coast. Lisbon lies in the western Iberian Peninsula on the Atlantic Ocean and the River Tagus. The westernmost areas of its metro area form the westernmost point of Continental Europe, which is known as Cabo da Roca, located in the Sintra Mountains.