9 nights Southampton, Lisbon, Gibraltar, Malaga, Cadiz, Southampton

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.

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.

Gibraltar  is a British Overseas Territory located at the southern tip of the Iberian Peninsula. It has an area of 6.7 km2 (2.6 sq mi) and is bordered to the north by Spain. The landscape is dominated by the Rock of Gibraltar at the foot of which is a densely populated town area, home to over 30,000 people, primarily Gibraltarians. It shares a maritime border with Morocco.

In 1704, Anglo-Dutch forces captured Gibraltar from Spain during the War of the Spanish Succession on behalf of the Habsburg claim to the Spanish throne. The territory was ceded to Great Britain in perpetuity under the Treaty of Utrechtin 1713. During World War II it was an important base for the Royal Navy as it controlled the entrance and exit to the Mediterranean Sea, which is only 8 miles (13 km) wide at this naval choke point. It remains strategically important, with half the world's seaborne trade passing through the strait. Today Gibraltar's economy is based largely on tourism, online gambling, financial services and cargo ship refuelling.

The sovereignty of Gibraltar is a point of contention in Anglo-Spanish relations because Spain asserts a claim to the territory. Gibraltarians rejected proposals for Spanish sovereignty in a 1967 referendum and, in a 2002 referendum, the idea of shared sovereignty was also rejected.

Málaga is a municipality, capital of the Province of Málaga, in the Autonomous Community of Andalusia, Spain. With a population of 569,130 in 2015, it is the second-most populous city of Andalusia and the sixth-largest in Spain. The southernmost large city in Europe, it lies on the Costa del Sol (Coast of the Sun) of the Mediterranean, about 100 kilometres (62.14 miles) east of the Strait of Gibraltar and about 130 km (80.78 mi) north of Africa.

Málaga's history spans about 2,800 years, making it one of the oldest cities in the world. According to most scholars, it was founded about 770 BC by the Phoenicians as Malaka From the 6th century BC the city was under the hegemony of Ancient Carthage, and from 218 BC, it was ruled by the Roman Republic and then empire as Malaca (Latin). After the fall of the empire and the end of Visigothic rule, it was under Islamic rule as Mālaqah for 800 years, but in 1487, the Crown of Castille gained control after the Reconquista. The archaeological remains and monuments from the Phoenician, Roman, Arabic and Christian eras make the historic center of the city an "open museum", displaying its history of nearly 3,000 years.

This important cultural infrastructure and the artistic heritage have culminated in the nomination of Málaga as a candidate for the 2016 European Capital of Culture.

The painter and sculptor Pablo Picasso, Hebrew poet and Jewish philosopher Solomon Ibn Gabirol and the actor Antonio Banderas were born in Málaga. The magnum opus of Cuban composer Ernesto Lecuona, "Malagueña", is named after the music of this region of Spain.

The most important business sectors in Málaga are tourism, construction and technology services, but other sectors such as transportation and logistics are beginning to expand. The Andalusia Technology Park (PTA), located in Málaga, has enjoyed significant growth since its inauguration in 1992. Málaga is the main economic and financial centre of southern Spain, home of the region's largest bank, Unicaja, and the fourth-ranking city in economic activity in Spain behind Madrid, Barcelona and Valencia.

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.