10 nights, from Miami, Florida

Miami, officially the City of Miami, is the cultural, economic and financial center of South Florida. Miami is the seat of Miami-Dade County, the most populous county in Florida. The city covers an area of about 56.6 square miles (147 km2), between the Everglades to the west and Biscayne Bay on the east; with a 2017 estimated population of 463,347, Miami is the sixth most densely populated major city in the United States. The Miami metropolitan area is home to 6.1 million people and the seventh-largest metropolitan area in the nation. Miami's metro area is the second-most populous metropolis in the southeastern United States and fourth-largest urban area in the U.S.

Miami is a major center, and a leader in finance, commerce, culture, media, entertainment, the arts, and international trade. The Miami Metropolitan Area is by far the largest urban economy in Florida and the 12th largest in the United States with a GDP of $344.9 billion as of 2017. In 2012, Miami was classified as an "Alpha−" level world city in the World Cities Study Group's inventory. In 2010, Miami ranked seventh in the United States and 33rd among global cities in terms of business activity, human capital, information exchange, cultural experience, and political engagement. In 2008, Forbes magazine ranked Miami "America's Cleanest City", for its year-round good air quality, vast green spaces, clean drinking water, clean streets, and citywide recycling programs. According to a 2009 UBS study of 73 world cities, Miami was ranked as the richest city in the United States, and the world's seventh-richest city in terms of purchasing power. Miami is nicknamed the "Capital of Latin America" and is the largest city with a Cuban-American plurality.

Greater Downtown Miami has one of the largest concentrations of international banks in the United States, and is home to many large national and international companies. The Civic Center is a major center for hospitals, research institutes, medical centers, and biotechnology industries. For more than two decades, the Port of Miami, known as the "Cruise Capital of the World", has been the number one cruise passenger port in the world. It accommodates some of the world's largest cruise ships and operations, and is the busiest port in both passenger traffic and cruise lines. Metropolitan Miami is also a major tourism hub in the southeastern U.S. for international visitors, ranking number two in the country after New York City.

Key West is an island and city in the Straits of Florida on the North American continent. The city lies at the southernmost end of U.S. Route 1, the longest north-south road in the United States. Key West is the southernmost city in the contiguous United States and the westernmost island connected by highway in the Florida Keys. The island is about 4 miles (6.4 km) long and 1 mile (1.6 km) wide, with a total land mass of 4.2 square miles (11 km2). Duval Street, its main street, is 1.1 miles (1.8 km) in length in its 14-block-long crossing from the Gulf of Mexico to the Straits of Florida and the Atlantic Ocean. Key West is about 95 miles (153 km) north of Cuba at their closest points.

The city is the county seat of Monroe County. The city boundaries include the island of Key West and all or part of several nearby islands: Sigsbee Park, Fleming Key, Sunset Key, and the northern part of Stock Island. The total land area of the city is 5.6 square miles (14.5 km2). Key West is the southern terminus of U.S. Route 1, State Road A1A, the East Coast Greenway and, before 1935, the Florida East Coast Railway.

Key West is 129 miles (208 km) southwest of Miami by air, about 160 miles (260 km) by car, and 106 miles (171 km) north-northeast of Havana. Key West is a port of call for many passenger cruise ships. The Key West International Airport provides airline service. Naval Air Station Key West is an important year round training site for naval aviation due to the tropical weather, which is also the reason Key West was chosen as the Winter White House of President Harry S. Truman. The central business district is located along Duval Street and includes much of the northwestern corner of the island. The official city motto is "One Human Family."

Roatán is an island in the Caribbean, about 65 kilometres (40 mi) off the northern coast of Honduras. It is located between the islands of Útila and Guanaja, and is the largest of the Bay Islands of Honduras.

The island was formerly known as Ruatan and Rattan. It is approximately 77 kilometres (48 mi) long, and less than 8 kilometres (5.0 mi) across at its widest point. The island consists of two municipalities: José Santos Guardiolain the east and Roatán, including the Cayos Cochinos, further south in the west.

Puerto Limón, commonly known as Limón (Spanish for "lemon"), is the capital city and main hub of Limón province, as well as of the cantón (county) of Limón in Costa Rica. It is the second largest city in Costa Rica, with a population of over 55,000, and is home of the Afro-Costa Rican community. Part of the community traces its roots to Italian, Jamaican and Chinese laborers who worked on a late nineteenth-century railroad project that connected San José to Puerto Limón. Until 1948, the Costa Rican government did not recognize Afro-Caribbean people as citizens and restricted their movement outside Limón province. As a result of this "travel ban", this Afro-Caribbean population became firmly established in the region, which influenced decisions not to move even after it was legally permitted. Nowadays, there is a significant outflow of Limón natives who move to the country's Central Valley in search for better employment and education. The Afro-Caribbean community speaks Spanish and Limonese Creole, a creole of English.

Puerto Limón contains two port terminals, Limón and Moín, which permit the shipment of Costa Rican exports as well as the anchoring of cruise ships. In 2016, the government pledged ₡93 million ($166,000) for a new cruise ship terminal for Puerto Limón.

Health care is provided for the city by Hospital Dr. Tony Facio Castro. Two small islands, Uvita Island and Isla de Pájaros, are just offshore.