21 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."

San Juan

Antigua is an island in the West Indies. It is one of the Leeward Islands in the Caribbean region and the main island of the country of Antigua and Barbuda. Antigua and Barbuda became an independent state within the Commonwealth of Nations on 1 November 1981.

Antigua means "ancient" in Spanish after an icon in Seville Cathedral, "Santa Maria de la Antigua" — St. Mary of the Old Cathedral. The name Waladli comes from the indigenous inhabitants and means approximately "our own". The island's circumference is roughly 87 km (54 mi) and its area 281 km2 (108 sq mi). Its populationwas 80,161 (at the 2011 Census). The economy is mainly reliant on tourism, with the agricultural sector serving the domestic market.

Over 32,000 people live in the capital city, St. John's. The capital is situated in the north-west and has a deep harbour which is able to accommodate large cruise ships. Other leading population settlements are All Saints (3,412) and Liberta(2,239), according to the 2001 census.

English Harbour on the south-eastern coast is famed for its protected shelter during violent storms. It is the site of a restored British colonial naval station called "Nelson's Dockyard" after Captain Horatio Nelson. Today English Harbour and the neighbouring village of Falmouth are known as a yachting and sailing destination and provisioning centre. During Antigua Sailing Week, at the end of April and beginning of May, an annual regatta brings a number of sailing vessels and sailors to the island to play sports.

On 6 September 2017, the Category 5 Hurricane Irma destroyed 90 percent of the buildings on the island of Barbuda. Residents were evacuated to Antigua.

Aruba is an island and a constituent country of the Kingdom of the Netherlands in the southern Caribbean Sea, located about 1,600 kilometres (990 mi) west of the main part of the Lesser Antilles and 29 kilometres (18 mi) north of the coast of Venezuela. It measures 32 kilometres (20 mi) long from its northwestern to its southeastern end and 10 kilometres (6 mi) across at its widest point. Together with Bonaire and Curaçao, Aruba forms a group referred to as the ABC islands. Collectively, Aruba and the other Dutch islands in the Caribbean are often called the Dutch Caribbean.

Aruba is one of the four countries that form the Kingdom of the Netherlands, along with the Netherlands, Curaçao, and Sint Maarten; the citizens of these countries are all Dutch nationals. Aruba has no administrative subdivisions, but, for census purposes, is divided into eight regions. Its capital is Oranjestad.

Unlike much of the Caribbean region, Aruba has a dry climate and an arid, cactus-strewn landscape. This climate has helped tourism as visitors to the island can reliably expect warm, sunny weather. It has a land area of 179 km2(69.1 sq mi) and is densely populated, with a total of 102,484 inhabitants at the 2010 Census. It lies outside Hurricane Alley.

Curaçao is a Lesser Antilles island in the southern Caribbean Sea and the Dutch Caribbean region, about 65 km (40 mi) north of the Venezuelan coast. It is a constituent country (Dutch: land) of the Kingdom of the Netherlands.