14 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.

Ponta Delgada is the largest municipality and economic capital of the Autonomous Region of the Azores in Portugal. It is located on São Miguel Island, the largest and most populous in the archipelago. The population in 2011 was 68,809, in an area of 232.99 square kilometres (89.96 square miles). There are 17,629 residents in the three central civil parishes that comprise the historical city: São Pedro, São Sebastião, and São José. Ponta Delgada became the region's administrative capital under the revised constitution of 1976; the judiciary and Catholic see remained in the historical capital of Angra do Heroísmo while the Legislative Assembly of the Azores was established in Horta.

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.

 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.