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.

Port Canaveral is a cruise, cargo and naval port in Brevard County, Florida, United States. It is one of the busiest cruise ports in the world with 3.9 million cruise passengers passing through during 2014. As a deep water cargo port, it has a high volume of traffic. Over 3,000,000 short tons (2,700,000 t) of bulk cargo moves through each year. Common cargo includes cement, petroleum and aggregate. The port has conveyors and hoppers for loading products directly into trucks, and facilities for bulk cargo containers. The channel is about 44 feet (13 m) deep. The port exports fresh citrus; bulk frozen citrus juice stored in one of the largest freezer warehouses in the state; cement and building materials. Ten ships, on average, enter the port each day.

Great Stirrup Cay is a small island that is part of the Berry Islands in the Bahamas. Norwegian Cruise Line purchased the island from the Belcher Oil Company in 1977 and developed it into a private island for their cruise ship passengers. The northern part of the island has a sandy beach surrounded by rocks with snorkeling areas. The southern part features a helicopter airfield (with a sign reading "Great Stirrup Cay International Airport"), a large area without vegetation, and numerous concrete blocks. These are all remnants of a previous U.S. military installation and satellite tracking station. The island's lighthouse was originally constructed in 1863 by the Imperial Lighthouse Service. Great Stirrup Cay is adjacent to Little Stirrup Cay, Royal Caribbean Cruises' private island.