Best of Jamaica 10-Day Itinerary

By Oliver Hill, author of Moon Jamaica

Ten days is a good length for a trip to Jamaica and provides enough time to relax on the beach while also venturing beyond the sun and sand for a mix of adventure and culture. Highlights include the cliff-jumping and scrumptious food of Negril’s West End, the culture and nightlife of Kingston, the coffee plantations in the Blue Mountains, and the beaches in Portland.

view over Montego Bay Jamaica — Start your trip in Montego Bay. Photo © lucky-photographer/iStock.

Day 1

Arrive at the airport in Montego Bay and check in for two nights at Wharf House. Splurge for a dinner at The Sugar Mill or HouseBoat Grill, or keep it casual and affordable at Scotchies for some authentic roadside jerk. Hit up Mobay Proper for an evening drink to gauge the scene along the Hip Strip.

Day 2

Tour Rose Hall Great House in the morning, then spend the afternoon lazing at Doctors Cave Beach or try your hand at kiteboarding by Sea Castles in the afternoon, wind permitting. Dine at Day-O Plantation followed by a play at Fairfield Theatre or a night out at Margaritaville.

a yellow boat along the shore of Seven Mile Beach in Jamaica — Enjoy the expansive views along Seven-Mile Beach. Photo © Oliver Hill.

Day 3

Head west to Negril for cliff jumping on the West End or a splash at Brighton’s Blue Hole Mineral Spring by late morning. Head to Chill Awhile for lunch and soak up some rays before taking a sunset stroll down Seven-Mile Beach. Try Hungry Lion or Pushcart Restaurant and Rum Bar for dinner before checking out some live reggae music on the beach at night.

Day 4

In the morning, drive to Savanna-la-Mar and then turn inland to Mayfield Falls or Blue Hole Gardens. Spend the morning exploring the falls and gardens, then head over to nearby Paradise Park for horseback riding or a swim in the river followed by a picnic. Alternatively, grab a bite at Sweet Spice in Sav, then stop at Eldin Washington Ranch for Reggae Horseback Riding in the afternoon on the way back to Negril.

waterfall pooling over rock into a green pool of water in Jamaica — Take a splash in the river near YS Falls. Photo © Oliver Hill.

Day 5

Drive east to YS Falls in Middle Quarters for a splash in the river and an adrenaline-fixing zipline. Grab some jerk chicken at YS before heading to nearby Appleton Estate to sample Jamaica’s best rum. Continue on to Treasure Beach in the late afternoon to check in for the night and sample the conch soup and fried fish at Jack Sprat.

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Day 6

Wake up with a dip at the beach in Great Bay before a mid-morning stroll to Back Sea Side. In the afternoon catch a canoe boat to Black River to spot alligators and birds or head straight to Pelican Bar, a one-of-a-kind watering hole and ramshackle fried fish joint built on stilts 1.5 kilometers (1 mile) offshore, for some snorkeling and Red Stripe. Cruise back to Treasure Beach for a second night.

front view of Devon House in Kingston, Jamaica — Grab some ice cream at Devon House. Photo © Oliver Hill.

Day 7

Leave early for Kingston to get there by late morning, sightsee downtown with a visit to the National Gallery followed by a stroll along Ocean Boulevard and around Coronation Market. Stop by Liberty Hall or Culture Yard before heading uptown for lunch at Opa! or Chilitos. After lunch, take a tour at nearby Bob Marley Museum. Pick up some souvenirs and grab an ice cream at Devon House and prepare for a night out at a club or street dance.

Day 8

Head up to the Blue Mountains before the late morning clouds roll in for a tour of Old Tavern Coffee Estate. Continue over to Portland to reach Port Antonio in time for an afternoon dip at Winnifred Beach or Frenchman’s Cove before dinner at Mockingbird Hill and a night out at Cristal Night Club or Natural Mystic Bar.

rapids of the White River in Jamaica — Go tubing on the White River. Photo © Oliver Hill.

Day 9

Depart for Ocho Rios, stopping at Firefly on the way to check out Noël Coward’s island digs. Lunch at Dor’s Fish Pot in Race Course or at Chris Café in Oracabessa and then head up to Mystic Mountain for a bobsled run and zipline tour through the canopy, or pet the sharks at Dolphin Cove. Take a late-afternoon dip and tube ride down the White River before dinner at Passage to India or Toscanini’s.

Day 10

Get up and on the road early to beat the crowds for a climb up Dunn’s River Falls before heading west toward Montego Bay for an afternoon departure. Stop by Green Grotto Caves or Greenwood Great House on your way, time permitting.

Oliver Hill

About the Author

A dedicated reggae fan from a young age, Oliver Hill began his lasting relationship with Jamaica like many Americans: through the island’s music. Friendships with fellow students of Jamaican heritage in high school ultimately led Oliver to visit the island, where he established a recording studio in a Kingston suburb in partnership with a local artist. Frequent trips to Spain and other destinations throughout his youth gave Oliver a global perspective on life and an unquenchable thirst for experiencing new places and cultures.

Later, a masters program in journalism at Columbia University took Oliver back to Jamaica with a film crew to shoot Coping with Babylon, a chronicle of contemporary Rastafarian philosophy that has appeared in international film festivals around the world and as part of an exhibition at the Smithsonian titled “Discovering Rastafari.”

Oliver has worked as a video editor, ornithologist, and financial writer, and currently works as a correspondent for mergermarket, a Financial Times Group publication, in Latin America.

For more information on Oliver’s film production company, check out Sonerito.com.

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