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. 

Málaga is a large city in the southern Spanish region of Andalucia and capital of the Malaga Province. The largest city on the Costa del Sol, Malaga has a typical Mediterranean climate and is also known as the birthplace of famous Spanish artist Pablo Picasso. The city offers beaches, hiking, architectural sites, art museums, excellent shopping and cuisine. While more laid back than Madrid or Barcelona, Malaga is still the center and transport hub for the hugely popular Costa del Sol region, which is flooded with tourists in the summer, and the city has certainly cashed in on the sun and sand, with lots of new construction as well as hotels and facilities geared to tourists. However, Malaga also offers some genuinely interesting historical and cultural attractions in its old city and its setting on the coast is still beautiful.

Barcelona – Spain's enchanting capital, second largest and most populous city. It is a huge city that vibrates with life, and there’s certainly not another city in the country to touch it for its sheer style, looks or energy. It is one of the world's leading tourist, economic, trade fair and cultural centers, 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. Barcelona is home to masterpieces of many great architects – the most famous of which is Antoni Gaudí. 

Madeira is a Portuguese archipelago situated in the north Atlantic Ocean, southwest of Portugal. The capital of Madeira is Funchal on the main island's south coast. Since 1976, the archipelago has been one of the two Autonomous regions of Portugal (the other being the Azores, located to the northwest). It includes the islands of Madeira, Porto Santo, and the Desertas, administered together with the separate archipelago of the Savage Islands. It is an outermost region of the European Union. Today, it is a popular year-round resort, being visited every year by about one million tourists. The region is noted for its Madeira wine, gastronomy, historical and cultural value, its flora and fauna, landscapes (Laurel forest) which are classified as a UNESCO World Heritage Site and embroidery artisans. Its annual New Year celebrations feature the largest fireworks show in the world, as officially recognised by Guinness World Records in 2006. The main harbour in Funchal is the leading Portuguese port in cruise liner dockings, being an important stopover for commercial and trans-Atlantic passenger cruises between Europe, the Caribbean and North Africa. Madeira is the second richest region of Portugal by GDP per capita, being only surpassed by Lisbon.

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.