Guadeloupe (sometimes known as the ''Butterfly Island''), a French overseas territory, is an island group in the southern Caribbean Sea. It is an archipelago of nine inhabited islands, including Basse-Terre, Grande-Terre, Marie-Galante, La Desirade, Iles des Saintes, Saint-Barthélemy, Iles de la Petite Terre, and Saint-Martin (French part of the island of Saint Martin). Guadeloupe is best known for its rich culture, volcano, beautiful scenery and wonderful beaches.

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!

Havana, officially Ciudad de La Habana, is the capital city, major port, and leading commercial centre of Cuba. The city is one of the 15 Cuban provinces. The city/province has 2.1 million inhabitants, the largest city in Cuba and the second largest in the Caribbean region, after Santo Domingo. The city extends mostly westward and southward from the bay, which is entered through a narrow inlet and which divides into three main harbours: Marimelena, Guanabacoa, and Atarés. The sluggish Almendares River traverses the city from south to north, entering the Straits of Florida a few miles west of the bay.

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.

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.