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.

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.

The small capital of the British Virgin Islands is located on the main island of Tortola and has about 9000 inhabitants. The city was founded in 1648 by Dutch settlers. The town has been destroyed on many occasions due to coming under siege. The oldest buildings that remain now date back to 1840. If you're looking to explore the city, the Botanical Garden is a good place to start. Then, you can make your way to the ferry terminal of the city where many beautiful yachts drop anchor.