Oranjestad, known as ("Orange Town"), is the capital and largest city of Aruba. In the local language, Papiamento, Oranjestad is also often referred to simply as "Playa". The city consists of hundreds of local stores where tourists usually buy their keepsakes. The city is also home to some of the island's local residents and also many governmental buildings. Along the main "drag" (Sasakiweg street) you will find most tourist walking around and shopping and can also see the cruise ships that bring more and more external tourism into the island everyday. Close to the cruise ships is the island's largest marina where you can find great docking space for your vessel.

Bridgetown is the capital and largest city of the nation of Barbados. It is the only city on Barbados and well over half the island's residents live there. It is the port of call for many cruise ships and is known for its duty-free shopping as much as for its more cultural and historical attractions.

Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Formerly the capital of the Netherlands Antilles prior to its dissolution in 2010, it has an estimated population of 150,000. Willemstad is home to the Curaçao synagogue, the oldest surviving synagogue in the Americas.

Cartagena is Colombia's most famous tourist destination on the Caribbean coast. The city is renowned for its colonial and colourful architecture. With a tropical climate, the city is also a popular beach destination. The city was founded on June 1, 1533, and named after Cartagena, Spain, itself after the original Carthage in Tunisia. However, settlement in this region around Cartagena Bay by various indigenous people dates back to 4000 BC. During the colonial period Cartagena served a key role in administration and expansion of the Spanish empire. It was a center of political and economic activity due to the presence of royalty and wealthy viceroys. In 1984 Cartagena's colonial walled city and fortress were designated a UNESCO World Heritage Site.

Puerto Limón, commonly known as Limón (Spanish for "lemon"), is the capital city and main hub of Limón province, as well as of the cantón (county) of Limón in Costa Rica. It is the sixth-largest city in Costa Rica, with a population of over 55,000 (including surrounding towns), and is home of a multicultural community. Part of the community traces its roots to Italian, Jamaican and Chinese laborers who worked on a late nineteenth-century railroad project that connected San José to Puerto Limón. Until 1948, the Costa Rican government did not recognize Afro-Caribbean people as citizens and restricted their movement outside Limón province. As a result of this "travel ban", this Afro-Caribbean population became firmly established in the region, which influenced the decision to not move even after it was legally permitted. Nowadays, there is an important outflow of Limón natives who move to the country's Central Valley in search for better employment and education. The Afro-Caribbean community speaks Spanish and Limonese Creole, a creole of English.