20 nights Bridgetown, Kingstown, Saint George, Fort de France, Pointe-a-Pitre, Philipsburg, Ponta Delgada, Lis

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.

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.

A Coruña is a city and municipality of Galicia, Spain. It is the second most populated city in the autonomous community and seventeenth overall in the country. The city is the provincial capital of the province of the same name, having also served as political capital of the Kingdom of Galicia from the 16th to the 19th centuries, and as a regional administrative centre between 1833 and 1982, before being replaced by Santiago de Compostela.

A Coruña is a busy port located on a promontory in the Golfo Ártabro, a large gulf on the Atlantic Ocean. It provides a distribution point for agricultural goods from the region.

Southampton is the largest city in the ceremonial county of Hampshire, England. It is 69 miles (111 km) south-west of London and 15 miles (24 km) west north-west of Portsmouth. Southampton is a major port and the closest city to the New Forest. It lies at the northernmost point of Southampton Water at the confluence of the Rivers Test and Itchen, with the River Hamble joining to the south of the urban area. The city, which is a unitary authority, has an estimated population of 253,651. The city's name is sometimes abbreviated in writing to "So'ton" or "Soton", and a resident of Southampton is called a Sotonian.

Significant employers in the city include Southampton City Council, the University of Southampton, Solent University, Southampton Airport, Ordnance Survey, BBC South, the NHS, ABP and Carnival UK. Southampton is noted for its association with the RMS Titanic, the Spitfire and more generally in the World War II narrative as one of the departure points for D-Day, and more recently as the home port of a number of the largest cruise ships in the world. Southampton has a large shopping centre and retail park, Westquay. In 2014, the city council approved a neighbouring followup Westquay South which opened in 2016–2017.

In the 2001 census Southampton and Portsmouth were recorded as being parts of separate urban areas; however by the time of the 2011 census they had merged apolitically to become the sixth-largest built-up area in England with a population of 855,569. This built-up area is part of the metropolitan area known as South Hampshire, which is also known as Solent City, particularly in the media when discussing local governance organisational changes. With a population of over 1.5 million this makes the region one of the United Kingdom's most populous metropolitan areas.