18 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."

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

Puntarenas is the capital and largest city in the Province of Puntarenas, on the Pacific coast of Costa Rica.

Cabo San Lucas  or simply Cabo, is a resort city at the southern tip of the Baja California Peninsula, in the Mexican state of Baja California Sur. As of 2015, the population of the city was 81,111 inhabitants. Cabo San Lucas together with San José del Cabo is known as Los Cabos. Together they form a metropolitan area of 305,983 inhabitants.

Cabo has been rated as one of Mexico's top 5 tourist destinations; it is known for its beaches, scuba diving locations, balnearios, the sea arch El Arco de Cabo San Lucas, and marine life. The Los Cabos Corridor has become a heavily trafficked vacation destination for tourists, with numerous resorts and timeshares along the coast between Cabo San Lucas and San José del Cabo.

Cabo houses a range of wildlife, including rays, sharks, birds, and a range of fish, such as mahi-mahi (dorado), and striped marlin.

Ensenada is a coastal city in Mexico, the third-largest in Baja California. Lying 125 kilometres (78 mi) south of San Diego on the Baja California Peninsula, it is locally referred to as La Cenicienta del Pacífico, "The Cinderella of the Pacific."

One of the first settlements founded in the Californias, Ensenada has emerged as a cruise ship destination, aerospace center, and a jumping-off point for Valle de Guadalupe, a local wine region. It is said that the first Vitis vinifera made it to the region's San Ignacio Mission in 1703, when Jesuit Padre Juan de Ugarte planted the first vineyards there.

Situated on the coastline of Bahía de Todos Santos—an inlet of the Pacific Ocean on the peninsula's Gold Coast—the Port of Ensenada is an important commercial, fishing, and tourist port. The city is home to a navy base, army base, and Ensenada Airport, a military airfield which doubles as an airport of entry into Mexico.

Ensenada is the municipal seat and cultural and commercial center of Ensenada Municipality, one of five into which the state is divided. As of 2015, the municipality had a population of 519,813.

Ensenada is backed by small mountain ranges. Proximity to the Pacific and a warm Mediterranean latitude create mild year-round weather. The rainy season during the winter is short and the area is prone to prolonged droughts, which can threaten its grape harvests. The National Park Constitution of 1857 created the Sierra de Juarez and San Pedro Martir National Parks, which maintain one of the best astronomical observatories in the country.

Ensenada is part of UNESCO´s Creative Cities Network since 2015.

San Francisco , officially the City and County of San Francisco, is the cultural, commercial, and financial center of Northern California. San Francisco is the 13th-most populous city in the United States, and the fourth-most populous in California, with 884,363 residents as of 2017. It covers an area of about 46.89 square miles (121.4 km2), mostly at the north end of the San Francisco Peninsula in the San Francisco Bay Area, making it the second-most densely populated large US city, and the fifth-most densely populated U.S. county, behind only four of the five New York City boroughs. San Francisco is also part of the fifth-most populous primary statistical area in the United States, the San Jose–San Francisco–Oakland, CA Combined Statistical Area (9.7 million residents).