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. 

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.

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.

Fort Lauderdale is a city in the U.S. state of Florida, 28 miles (45 km) north of Miami. The city is a popular tourist destination, with an average year-round temperature of 75.5 °F (24.2 °C), and 3,000 hours of sunshine per year. Greater Fort Lauderdale which takes in all of Broward County hosted 12 million visitors in 2012, including 2.8 million international visitors. The district has 561 hotels and motels comprising nearly 35,000 rooms. Greater Fort Lauderdale has over 4,000 restaurants, 63 golf courses, 12 shopping malls, 16 museums, 132 nightclubs, 278 parkland campsites, and 100 marinas housing 45,000 resident yachts. Fort Lauderdale is named after a series of forts built by the United States during the Second Seminole War. The forts took their name from Major William Lauderdale (1782–1838), younger brother of Lieutenant Colonel James Lauderdale. William Lauderdale was the commander of the detachment of soldiers who built the first fort.

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.

Little San Salvador Island, also known as Half Moon Cay, is one of about 700 islands that make up the archipelago of The Bahamas. It is a private island, owned by Holland America Line, which uses it as a port of call for the cruise ships it operates in the region. Prior to being owned by HAL, Little San Salvador was the private island of Norwegian Cruise Line. The island is also a significant nesting area for waterfowl. Activities offered on the island include swimming, sunbathing, scuba diving, jet-skiing, cycling, and snorkeling. Deep-sea fishing, parasailing, glass-bottom boat rides, and nature walks also are available. A variety of water toys are available for rent, including Hobie catamarans, Sunfish sailboats, windsurfing sailboards, and kayaks.

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.