17 nights Miami, San Juan, Philipsburg, Fort de France, Bridgetown, Funchal, Casablanca, Barcelona

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.

San Juan

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.

Casablanca located in the central-western part of Morocco and bordering the Atlantic Ocean, is the largest city in Morocco. It is also the largest city in the Maghreb region, as well as one of the largest and most important cities in Africa, both economically and demographically.

Casablanca is Morocco's chief port and one of the largest financial centers on the continent. According to the 2014 population estimate, the city has a population of about 3.35 million in the urban area and over 6.8 million in the Casablanca-Settat region. Casablanca is considered the economic and business center of Morocco, although the national political capital is Rabat.

The leading Moroccan companies and international many corporations doing business in the country have their headquarters and main industrial facilities in Casablanca. Recent industrial statistics show Casablanca retains its historical position as the main industrial zone of the country. The Port of Casablanca is one of the largest artificial ports in the world, and the second largest port of North Africa, after Tanger-Med 40 km (25 mi) east of Tangier. Casablanca also hosts the primary naval base for the Royal Moroccan Navy.

 Barcelona is a city in Spain. It is the capital and largest city of Catalonia, as well as the second most populous municipality of Spain. With a population of 1.6 million within city limits, its urban area extends to numerous neighbouring municipalities within the Province of Barcelona and is home to around 4.8 million people, making it the sixth most populous urban area in the European Union after Paris, London, Madrid, the Ruhr area and Milan. It is one of the largest metropolises on the Mediterranean Sea, located on the coast between the mouths of the rivers Llobregat and Besòs, and bounded to the west by the Serra de Collserola mountain range, the tallest peak of which is 512 metres (1,680 feet) high.

Founded as a Roman city, in the Middle Ages Barcelona became the capital of the County of Barcelona. After merging with the Kingdom of Aragon, Barcelona continued to be an important city in the Crown of Aragon as an economic and administrative centre of this Crown and the capital of the Principality of Catalonia. Barcelona has a rich cultural heritage and is today an important cultural centre and a major tourist destination. Particularly renowned are the architectural works of Antoni Gaudí and Lluís Domènech i Montaner, which have been designated UNESCO World Heritage Sites. The headquarters of the Union for the Mediterranean are located in Barcelona. The city is known for hosting the 1992 Summer Olympics as well as world-class conferences and expositions and also many international sport tournaments.

Barcelona is one of the world's leading tourist, economic, trade fair and cultural centres, and its influence in commerce, education, entertainment, media, fashion, science, and the arts all contribute to its status as one of the world's major global cities. It is a major cultural and economic centre in southwestern Europe, 24th in the world (before Zürich, after Frankfurt) and a financial centre. In 2008 it was the fourth most economically powerful city by GDP in the European Union and 35th in the world with GDP amounting to €177 billion. In 2012 Barcelona had a GDP of $170 billion; and it was leading Spain in employment rate in that moment.

In 2009 the city was ranked Europe's third and one of the world's most successful as a city brand. In the same year the city was ranked Europe's fourth best city for business and fastest improving European city, with growth improved by 17% per year, and the city has been experiencing strong and renewed growth for the past three years. Since 2011 Barcelona has been a leading smart city in Europe. Barcelona is a transport hub, with the Port of Barcelona being one of Europe's principal seaports and busiest European passenger port, an international airport, Barcelona–El Prat Airport, which handles over 50 million passengers per year, an extensive motorway network, and a high-speed rail line with a link to France and the rest of Europe.