How To Get To Cayman Islands Traveling by airplane is the easiest way to get to Cayman Islands. It is the quickest mode of transportation, as well as the most direct among all options. There are a number of airline companies that offer flights to Cayman Islands from some cities in the United States. Cayman Airways has flights from big U.S. cities such as New York, Miami, Chicago, Tampa, Orlando, and Washington. The airline also serves Jamaica, Honduras, and the islands of the Cayman Islands. American Airlines, Delta, Northwest, Continental, British Airways, and Air Canada are some of the other companies that operate flights from mainland North America and abroad to Cayman Islands. Cruise shops are another way to reach Cayman Islands. There is a popular Caribbean cruise ship port located in Grand Cayman Island where several ships stop and pass by. Some of the cruise line companies that have a stopover or dock at this port include the Radisson Seven Seas, Royal Caribbean, Princes