
essentials
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.
Every day in Jamaica is a cultural experience. Iconic activities include cooling off in the river, playing dominoes at the corner bar, stopping for jerk chicken or pepper shrimp roadside, dancing barefoot to live reggae on the beach, and hanging out late into the night at an impromptu neighborhood street party. Jamaica’s boisterous, fun-loving people have an intoxicating energy. Even if you’re just beachcombing in tourist havens Negril or Montego Bay, there’s no escaping the local flavor in Jamaica, and that’s what makes it “irie.” For more immersion, head to the hills of Cockpit Country and meet authentic Maroon and Rastafarian communities.
Jamaica is an island of year-round festivals, from food fests to annual reggae concerts and cultural celebrations. Keep a lookout for billboards and flyers, or ask anyone in town. Scheduling your trip around one of the festivals is a great idea, too. Pick either the first week of February for Bob Marley Birthday Bash celebrations and concerts in Negril, or July for the annual Sumfest concert in Montego Bay. If you’re into cultural ceremonies, don’t miss the Annual Maroon Festival in Accompong Town, held on the south coast during the first week of January. Then hop on over to the annual Jamaica Jazz & Blues Festival held the second or third week of January.
Lebawit Lily Girma is a freelance travel writer and photographer who splits her time between Washington, D.C., Belize, and Jamaica. A serial expat, she has traveled the Caribbean for the past ten years and lived for extended periods in Jamaica and Belize. Lily's articles and photography, which focus on culture and adventure, have been published in New York Magazine, CNN Travel, The Travel Channel, American Way, BBC Travel, and others. She's the author of Moon Belize (Avalon Travel/Perseus Books). Follow Lily's journey on Sunshine and Stilettos and look for her new Jamaica guidebook to be released this fall.