Bridgetown is the island's largest city and is a vibrant and historic cultural gem. The city was founded by the British, meaning there is a terrific mix of old and new on the island with historic British colonial buildings alongside modern structures such as shopping centres and financial institutions. Always a lively city, there is a large amount of shopping, dining and cultural experiences to discover. Street vendors provide colour and character to the streets and the local bars and restaurants are the perfect way to immerse yourself in the Caribbean culture.

The seaside city of Roseau, capital of Dominica, has a rich history. The city boasts Creole architecture from the eighteenth century, and its Old Market, which vendors now flock to to sell their handicrafts and produce, is a former site for slave auctions. Visitors can immerse themselves in the nation's history at the Dominica Museum or see the local flora and fauna at the Dominica Botanical Gardens.

Charlestown is located on the Caribbean island of Nevis and is the capital of the Republic of Saint Kitts and Nevis. The town was built on the protected leeward side of the island and is the birthplace of Alexander Hamilton.

San Juan is the capital and largest city of Puerto Rico. As a cruising hot spot in the Caribbean, San Juan offers all of the amenities and attractions of a modern city. The city is divided into Old and New San Juan. Old San Juan dates back five centuries and is known for its colourful buildings and old forts, which once protected the island. El Morro is a well-known fort that now houses a small military museum. At the city walls that surround San Juan is The Paseo de la Princesca, a beautiful promenade with shops, restaurants, and gorgeous views.