11 nights, from Tampa Florida

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."

The city of Cartagena, known in the colonial era as Cartagena de Indias, is a major port founded in 1533, located on the northern coast of Colombia in the Caribbean Coast Region. It was strategically located between the Magdalena and Sinú rivers and became the main port for trade between Spain and its overseas empire, establishing its importance by the early 1540s. During the colonial era it was a key port for the export of Peruvian silver to Spain and for the import of enslaved Africans under the asiento system. It was defensible against pirate attacks in the Caribbean. It is the capital of the Bolívar Department, and had a population 971,592 as of 2016. It is the fifth-largest city in Colombia and the second largest in the region, after Barranquilla. The urban area of Cartagena is also the fifth-largest urban area in the country. Economic activities include the maritime and petrochemicals industries, as well as tourism.

The city was founded on June 1, 1533, and named after Cartagena, Spain, settlement in the region around Cartagena Bay by various indigenous people dates back to 4000 BC. During the Spanish colonial period Cartagena served a key role in administration and expansion of the Spanish empire. It was a center of political, ecclesiastical, and economic activity. In 1984, Cartagena's colonial walled city and fortress were designated a UNESCO World Heritage Site.

The city of Cartagena, known in the colonial era as Cartagena de Indias, is a major port founded in 1533, located on the northern coast of Colombia in the Caribbean Coast Region. It was strategically located between the Magdalena and Sinú rivers and became the main port for trade between Spain and its overseas empire, establishing its importance by the early 1540s. During the colonial era it was a key port for the export of Peruvian silver to Spain and for the import of enslaved Africans under the asiento system. It was defensible against pirate attacks in the Caribbean. It is the capital of the Bolívar Department, and had a population 971,592 as of 2016. It is the fifth-largest city in Colombia and the second largest in the region, after Barranquilla. The urban area of Cartagena is also the fifth-largest urban area in the country. Economic activities include the maritime and petrochemicals industries, as well as tourism.

The city was founded on June 1, 1533, and named after Cartagena, Spain, settlement in the region around Cartagena Bay by various indigenous people dates back to 4000 BC. During the Spanish colonial period Cartagena served a key role in administration and expansion of the Spanish empire. It was a center of political, ecclesiastical, and economic activity. In 1984, Cartagena's colonial walled city and fortress were designated a UNESCO World Heritage Site.

Colon

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.

Cozumel is an island and municipality in the Caribbean Sea off the eastern coast of Mexico's Yucatán Peninsula, opposite Playa del Carmen, and close to the Yucatán Channel. The municipality is part of the state of Quintana Roo, Mexico.

The economy of Cozumel is based on tourism, with visitors able to benefit from the island's balnearios, scuba diving, and snorkeling. The main town on the island is San Miguel de Cozumel.