Major airlines fly to Jamaica, as do discount carriers like Spirit and JetBlue. Visas are not required of U.S. or Canadian visitors for stays of up to 90 days. Jamaican immigration officers are some of the friendliest in the Caribbean—know your return date and flight for forms—and customs may randomly search your bags for undeclared items. Montego Bay’s Sangster International Airport is well-connected to the rest of the island via public and private transportation. Upon exiting the airport, hop into your resort’s shuttle or bus if you’re staying in Montego Bay. If heading to Negril and other parts, your best bet is to book a ride with Clives Transport Jamaica—an affordable, reliable, locally-owned company offering shared vans or private transfers.

Once at your destination, get the number of a trusted taxi driver from your guesthouse or resort. All licensed taxis have red license plates, but it’s safest to know your driver ahead of time. Individual drivers and tour operators offer long-distance excursions, or you can rent your own car with an international driver's license. Just be sure you have a recent map and instructions from a local. While the highways are paved and reliable, not all roads are created equal in Jamaica and signs aren’t always clear.