Grenada is an island country consisting of Grenada itself and six smaller islands at the southern end of the Grenadines in the southeastern Caribbean Sea. The islands are of volcanic origin with extremely rich soil. Grenada's interior is very mountainous with Mount St. Catherine being the highest at 840 m (2,760 ft). Several small rivers with beautiful waterfalls flow into the sea from these mountains. It is also known as "Island of Spice" because of the production of nutmeg and mace crops of which it is one of the world's largest exporters.

Bridgetown is the capital and largest city of the nation of Barbados. It is the only city on Barbados and well over half the island's residents live there. It is the port of call for many cruise ships and is known for its duty-free shopping as much as for its more cultural and historical attractions.

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).

Ponce is both a city and a municipality in the southern part of Puerto Rico. The city is the seat of the municipal government. The city of Ponce, the second largest in Puerto Rico outside of the San Juan metropolitan area, is named for Juan Ponce de León y Loayza, the great-grandson of Spanish conquistador Juan Ponce de León. Ponce is often referred to as La Perla del Sur (The Pearl of the South), La Ciudad Señorial (The Noble, or Lordly, City), and La Ciudad de las Quenepas (Genip City). The city serves as the governmental seat of the autonomous municipality as well as the regional hub for various Government of Puerto Rico entities, such as the Judiciary of Puerto Rico. It is also the regional center for various other Commonwealth and federal government agencies. The Municipality of Ponce, officially the Autonomous Municipality of Ponce, is located in the Southern Coastal Plain region of the island, south of Adjuntas, Utuado, and Jayuya; east of Peñuelas; west of Juana Díaz; and bordered on the south by the Caribbean Sea.

Santo Domingo, known officially as Santo Domingo de Guzmán, is the capital and largest city in the Dominican Republic. Its metropolitan population was 2,084,852 in 2003, and estimated at 2,253,437 in 2006. The city is located on the Caribbean Sea, at the mouth of the Ozama River. Founded by Bartholomew Columbus in 1496, it is the oldest continuously inhabited European settlement in the Americas, and was the first seat of Spanish colonial rule in the New World. It lies within the boundaries of the Distrito Nacional (D.N.; "National District"), itself bordered on three sides by Santo Domingo Province. 

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.

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.