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.

The Dominican Republic is a sovereign state on the island of Hispaniola, in the Greater Antilles archipelago in the Caribbean Caribbean region. Though known for its wonderful beaches, all-inclusive resorts and golfing, it has a varied terrain comprising rainforest, savannah and highlands, including Pico Duarte, the Caribbean’s tallest mountain. For the adventure tourist this Caribbean country offers a diverse countryside comprising tropical rainforests, arid desert expanses, alpine ranges and steamy mangrove swamps. It's a playground for trekkers, mountain bike enthusiasts and water-sport junkies!

Saint Thomas is an island in the Caribbean Sea and with the islands of Saint John, Saint Croix, and Water Island a county and constituent district of the United States Virgin Islands (USVI), an unincorporated territory of the United States. Located on the island is the territorial capital and port of Charlotte Amalie. As of the 2000 census, the population of Saint Thomas was 51,181 about 47% of the US Virgin Island total. The district has a land area of 31.24 square miles (80.9 km2).

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.

Grand Cayman is the largest of the Cayman Islands, a British Overseas Territory in the Caribbean. George Town, its capital, is home to the Cayman Islands National Museum, dedicated to Caymanian heritage.  There are fast food restaurants, night clubs, and resorts on the western side of the island down to George Town. The eastern districts have more restaurants specialising in native Caymanian cuisine. Because of its clubs, resorts, and hotels, Seven Mile Beach has the largest concentration of visitors and tourists on the island. Watersports such as scuba diving and snorkeling are among the most popular activities on Grand Cayman as the island is known for its coral reefs and underwater sea walls along with a number of shipwrecks.

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.

Falmouth is the chief town and capital of the parish of Trelawny in Jamaica. It is situated on Jamaica's north coast 18 miles east of Montego Bay. It is noted for being one of the Caribbean's best-preserved Georgian towns. Founded by Thomas Reid in 1769, Falmouth flourished as a market centre and port for forty years at a time when Jamaica was the world's leading sugar producer. It was named after Falmouth, Cornwall in the United Kingdom, the birthplace of Sir William Trelawny, the Governor of Jamaica, who was instrumental in its establishment. The town was meticulously planned from the start, with wide streets in a regular grid, adequate water supply, and public buildings.