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. 

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 Croix is an island in the Caribbean Sea, and a county and constituent district of the United States Virgin Islands (USVI), an unincorporated territory of the United States. It is the largest of the U.S. Virgin Islands, being 28 by 7 miles (45 by 11 km). However, the territory's capital, Charlotte Amalie, is located on Saint Thomas. St. Croix, like many other Caribbean islands, has tourism as one of its main sources of revenue. However, there are a number of other industries on the island to help support the economy. St. Croix was once an agricultural powerhouse in the Caribbean, but ended with the rapid industrialization of the island's economy in the 1960s. Buck Island Reef National Monument preserves a 176 acre (71 ha) island just north of Saint Croix and the surrounding reefs. This is a popular destination for snorkelers.

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!

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.

Tortola is the largest and most populated of the British Virgin Islands, a group of islands that form part of the archipelago of the Virgin Islands. It has a surface area of 55 square kilometres (21 square miles) with a total population of 23,908, with 9400 residents in Road Town. Mount Sage is its highest point at 530 metres (1,740 feet) above sea level. It features several white-sand beaches, including Cane Garden Bay and Smuggler’s Cove.

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.

Phillipsburg is a town in Warren County, New Jersey, in the United States. It was incorporated as a town by an act of the New Jersey Legislature on March 8, 1861, from portions of Phillipsburg Township (now Lopatcong Township). The town was named for William Phillips, an early settler of the area. Phillipsburg had historically benefited from being a major transportation hub, situated at the confluence of the Delaware and Lehigh rivers. Phillipsburg served as the western terminus of the Morris Canal for approximately 100 years from the 1820s to 1920s, which connected the city by water to the industrial and consumer centers of the New York City area, with connections westward via the Lehigh Canal and Delaware Canal across the Delaware.

Basse-Terre Island is the name of the western-half of Guadeloupe proper, in the Lesser Antilles. Despite its name, Basse-Terre Island (literally "Low Land" Island, "Down Land" Island) is the highest island of Guadeloupe, rising to 1,467 metres (4,813 feet) above sea level at the Soufrière volcano. Above the city of Basse-Terre on a mountain road, is the village of Saint-Claude, at the base of the Soufrière volcano. The village is noted for its coffee and banana plantations & stately homes. Tours to ascend the Soufrière can be arranged. A few beaches are located along the coast, north and south of the city of Basse-Terre. There are also fishing areas.

Pointe-à-Pitre is the largest city of Guadeloupe, an overseas région and département of France located in the Lesser Antilles, of which it is a sous-préfecture, being the seat of the Arrondissement of Pointe-à-Pitre. Well-preserved 19th century buildings line the older streets such as Rue Achille and René-Boisneuf, and the bustling markets are a great place to soak up some local color with their tropical produce piled high, aromatic spices, and vendors dressed in flamboyant attire. One of the main tourist attractions in the city is the Place de la Victoire, a park surrounded by lovely homes and restaurants.