San Juan, officially Municipio de la Ciudad Capital San Juan Bautista (Municipality of the Capital City, Saint John the Baptist), is the capital and most populous municipality in Puerto Rico, an unincorporated territory of the United States. As of the 2000 census, it has a population of 658,304 making it the 42nd-largest city under the jurisdiction of the United States. San Juan was founded by Spanish colonists in 1521, who called it Ciudad de Puerto Rico ("Rich Port City"). Puerto Rico's capital is the second oldest European-established city in the Americas, after Santo Domingo, in the Dominican Republic. Several historical buildings are located in San Juan; among the most notable are the city's former defensive forts, Fort San Felipe del Morro and Fort San Cristóbal, and La Fortaleza, the oldest executive mansion in continuous use in the Americas. 

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.

Cozumel is an island in the Caribbean Sea off the eastern coast of Mexico's Yucatán Peninsula, opposite Playa del Carmen, and close to the Yucatán Channel. The island is covered with mangrove forest which has many endemic animal species. Cozumel is a flat island based on limestone, resulting in a karst topography. There are a number of visitors to the island's balnearios, scuba diving, and snorkeling. The main town on the island is San Miguel de Cozumel. The islands belongs to Cozumel Municipality of the state of Quintana Roo, Mexico.

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.

Tampa is a Gulf Coast Bay city in the U.S. state of Florida. It serves as the county seat for Hillsborough County. Tampa is located on the west coast of Florida. The population of Tampa in 2000 was 303,447. According to the 2009 estimates, the city's population had grown to 343,890, making it the 54th largest city in the United States. The current location of Tampa was once inhabited by various indigenous cultures, most recently the Tocobaga. It was spotted by Spanish explorers in the early 16th century, but there were no permanent American or European settlements in the area until 1824, when the US Army established a frontier outpost called Fort Brooke at the site of today's Tampa Convention Center. The village of Tampa began as a small group of pioneers who settled near the fort for protection from the Seminole population in the area.

One of the major tourist areas in St. Lucia, Castries, is a port of call for cruise ships. They dock at Pointe Seraphine, to the north of the harbour, which is also a duty-free shopping centre. Beaches are also a major draw for tourists, and there are several in or very near Castries. The city doesn't have a huge amount to offer visitors, and it's usually just a place that you'll pass through on your way to the more obvious attractions of Saint Lucia - but it's worth watching those marvellous cruise ships that visit Saint Lucia dock!

Key West is an island in the Straits of Florida on the North American continent at the southernmost tip of the Florida Keys. It is considered the southernmost city in the continental United States. The city also occupies nearby islands and portions of nearby islands. It’s popularly known for its stunning beaches, coral reefs – destinations for diving and snorkeling.

George Town is a city situated on Grand Cayman island of the Cayman Islands. It serves as the capital of the Cayman Islands, in the British West Indies. As of 2007, the city had a population of 28,836, making it the second largest city (by population) of all the British Overseas Territories. George Town's famous Seven Mile Beach is a long crescent of coral-sand beach extending up to the West Bay region of Grand Cayman and is the most popular and populated area for tourists on the island.

Charlotte Amalie, located on St. Thomas, is the capital and largest city of the U.S. Virgin Islands. Founded in 1666 as Taphus (meaning "beer houses" or "beer halls"), the town has been inhabited for centuries. Hundreds of ferries and yachts pass through town each week, and at times the population more than doubles. The city is known for its Danish colonial architecture, building structure and history, and a dozen streets and places throughout the city have Danish names. Charlotte Amalie has buildings of historical importance including St. Thomas Synagogue, the second-oldest synagogue in the Western Hemisphere, and Frederick Lutheran Church, the oldest Lutheran church in the Western Hemisphere. The town has a long history of pirates, especially stories of Bluebeard and Blackbeard (Edward Teach). In the 17th century, the Danes built both Blackbeard's Castle and Bluebeard's Castle attributed to the pirates. Blackbeard's Castle is a U.S.National Historic Landmark. Another tourist attraction is Fort Christian, the oldest standing structure in the Virgin Islands Archipelago. A copy of the Liberty Bell is in Emancipation Park, which is a tourist attraction.