Jamaican Roots & Culture: 10-Day Itinerary

Delve into the pulsating cultural milieu that shapes and defines Jamaican society. The roots of Jamaican popular music will become vivid with this tour, designed to immerse visitors in the island’s singular musical gold mine. Keep tabs on the weekly events calendars in Kingston and Negril to plan your time in these areas.

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

Day 1

Arrive in Montego Bay for one night at the Spanish Court. If you arrive in the morning, visit Rose Hall Great House or Bellefield Great House for a step back in time with a stop at Scotchies for jerk either before or after the tour. Visit the Gallery of West Indian Art for some inspiration before dinner at Pier 1 or the HouseBoat Grill. Hit up Margaritaville to mingle and “wine” with visitors and locals if you still have the energy before bed.

Day 2

Head to Doctors Cave Beach in the morning and then to Negril in the afternoon, stopping at Niah’s Patties for a bite before catching sunset and dinner on the cliffs at Tensing Pen or Pushcart Restaurant and Rum Bar. Check out the night’s live reggae band on the beach or hit the club at The Jungle.

Day 3

Make a loop from Negril to Blue Hole Gardens or Mayfield Falls before swinging back around to Half Moon Beach along the Hanover coast. Head back to Negril for dinner at Hungry Lion or Zest Restaurant at The Cliff.

clear pool of water among lush green gardens in Jamaica
Blue Hole Gardens in Petersfield. Photo © Oliver Hill.

Day 4

Leave for Kingston in the morning, stopping in Belmont to pay respects to a reggae legend at Peter Tosh Memorial Garden. Make a pit stop in Middle Quarters for “swimps,” or pepper shrimp, and then take a break at Scott’s Pass, Clarendon, to meet the Rasta elders at the headquarters of the Nyabinghi House of Rastafari before continuing on to Kingston for the night.

Day 5

Hit Kingston’s cultural sights, or any combination of the Bob Marley Museum, Tuff Gong Recording Studio, Culture Yard, and the National Gallery. Visit Cap Calcini to pick up some oldies reggae vinyl before heading out to Hellshire Beach for an early supper of fried fish, festival, and bammy at Shorty’s, or dine at Gloria’s in Port Royal before a night out on the town at Fiction Fantasy or at a street dance.

Day 6

Leave in the morning for Jamnesia Surf Club in Bull Bay to ride waves with Billy “Mystic” Wilmot and his family, followed by dinner and an overnight stay in one of their bungalows. Time your stay to fall on the last Saturday of the month to witness the musical talents of the host family and friends riffing at Jamnesia Sessions.

dj spinning at a club in Kingston Jamaica
Gabre Selassie at Kingston Dub Club. Photo © Oliver Hill.

Day 7

Spend the morning sampling the ritualized Rasta life at Bobo Hill if you’re in the mood for some serious worship (be sure to call ahead to Priest Daniel Samuel, tel. 876/422-3471). Visit Reggae Falls or Cane River Falls in the afternoon before heading back to Kingston. Dine on Indian cuisine at Pushpa’s or Tamarind and then head up to Skyline Drive for some roots music and a drink at Gabre Selassie’s Kingston Dub Club, especially lively on Sundays.

Day 8

Leave in the morning for Port Antonio, checking in at Great Huts, Drapers San, or Goblin Hill. Spend the afternoon at Reach Falls or on the beach with a quick visit to Folly Mansion, a dilapidated old mansion located between the Folly Oval cricket field and the sea.

Day 9

Depart first thing for Ocho Rios, stopping in Charles Town to take in some Maroon history, hiking, and swimming at Asafu Yard. In Ocho Rios, visit Konoko Falls to check out the iguanas and take an evening dip before dinner at Tropical Vibes on Fisherman’s Beach.

waterfall pouring into a swimming hole surrounded by lush forest in Jamaica
Head to Blue Hole River for a dip. Photo © johany/iStock.

Day 10

Visit Blue Hole River for swimming and a bit of light hiking in the morning before making your way to Montego Bay for an evening departure. Stop by Burwood Beach in Trelawny on the way for a quick dip, time permitting.

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