Getting to the Caribbean from most cities in the United States and Canada is easy. Major Airlines, including American, Delta, United, Jet Blue, Alaska Airlines, Southwest Airlines and Air Canada fly direct to Caribbean destinations from dozens of cities in both countries including New York, Chicago, Boston, Charlotte, Atlanta, Miami, Dallas, Houston and Washington DC.
Visitors will have little trouble finding flights to San Juan PR, St. Martin, Providenciales in the Turks and Caicos, Barbados, Jamaica, Grand Cayman and the Dominican Republic. Many exceptional smaller islands have airports that can only accommodate smaller planes, or ferries so when visiting Anguilla, St John, St Barts, Mustique, Canouan, Virgin Gorda and other gems, you’ll need to book an inter-island connecting flight.
For US citizens traveling to the U.S. Virgin Islands or Puerto Rico is considered a domestic flight, so no passport is required. However for the rest of the Caribbean islands you’ll want to have a passport in hand that is valid for at least six months from the arrival date. For residents of countries in North America and the European Union, visas are not typically required for vacation visits to Caribbean islands.