Don’t Worry About a Thing On Your Jamaican Weekend Vacation

For a relatively small island (the total population is a smidge higher than Chicago), Jamaican culture looms large on the international stage. From music styles ranging from reggae and dancehall and only-in-Jamaica jerk spices and exceptionally good rum, the country has influenced how people dance, eat and drink all over the world.

Make a trip to this bucket-list tropical paradise to experience the island firsthand. From the buzzy capital of Kingston to the low-key beach town of Negril, you can explore Jamaica at your own speed, with plenty of cerulean water and verdant forests along the way.

As always, check for travel restrictions and closures before planning your trip.

Friday: Discover Kingston Culture

Start your day at Eleni’s Bakery, where you can choose between sweet pastries or savory breakfast bites, then take your coffee to go from the Café Blue just next door. The coffee shop serves beans from the nearby Blue Mountains (and sells beans by the bags, as well).

After breakfast, head to the Bob Marley Museum, situated right in the heart of Kingston. The museum is located in the reggae giant’s former home and features memorabilia and personal artifacts from the late singer, as well as a gallery of photos highlighting Marley’s incredible career.

Art aficionados should also visit the National Gallery of Jamaica (one of the largest art collections in the Caribbean) or the Olympia Gallery (a stunning sculpture garden and two floors of local art in a residential complex). And history buffs will want to visit Port Royal to check out Fort Charles and learn more about 17th-century pirates.

For lunch, try Chillin’ Restaurant & Bar for authentic Jamaican cuisine or the South Avenue Grill for classic Caribbean fare. Then take a stroll around Emancipation Park, which was built to memorialize the end of slavery in Jamaica in 1834.

Afterward, head to the Devon House, a heritage site located at the former home of Jamaica’s first Black millionaire. Don’t forget to try the world-famous ice cream sold here, as well. If you have time, head to the Trench Town Culture Yard, a heritage site that’s said to be the birthplace of reggae.

Later, make your way back to Devon House for dinner at the Steak House on the Verandah for dry-aged steak and fresh seafood served on a terrace. Then put your dancing shoes on and head to Dub Club, one of Kingston’s most popular reggae dance halls for a fun night on the town.

Saturday: Get Outdoors in Negril

Set an early alarm to head out before sunrise to Negril. The drive is long (3.5 hours), but well worth it to get a full sense of the country over a short trip. Once in town, dig in to a simple and healthy breakfast at Just Natural, a family-owned vegetarian and seafood restaurant that’s a favorite among locals.

After fueling up, it’s time to wind down on the sand. Pick a spot along Seven Mile Beach and spend a few hours soaking up the sun or swimming in the crystal-clear waters. Adventure seekers can embark on a snorkeling or scuba diving adventure, while leisure lovers can sip on a refreshing cocktail while watching the calming waves in the distance.

For lunch, don’t stray far from the beach — choose a restaurant where you can eat by the water. Fireman’s Lobster Pit is a great option for a super-fresh shellfish with a view.

Afterward, head to the 289-acre Royal Palm Reserve to wander around luscious greenery and get up close and personal with the flora and fauna native to Negril (think: palm trees, butterflies and crocodiles). Let the eco-tour continue at Barney’s Flower & Hummingbird Garden, where you can admire tropical flowers and vibrantly colored hummingbirds in this enchanting setting.

Catch the sunset (and sip on a Red Stripe) at Rick’s Café, one of the most popular restaurants in Negril. Rick’s is famous for its breathtaking views of the sunset, as well as its cliffs where daredevils jump into the picturesque waters below.

For dinner, visit 3 Dives for a hearty Jamaican meal of either seafood or jerk chicken. If you’re staying in Kingston tonight, hop back in the car. Otherwise, head to the Jungle — one of the best nightclubs in town — and dance the rest of the night away to reggae and Caribbean jams.

Sunday: Explore Montego Bay

Montego Bay is resort-studded for good reason. Today, you’ll visit this north coast city, three hours from Kingston or a little over an hour from Negril. At the Pelican Grill, order the traditional ackee and saltfish for an authentic Jamaican breakfast.

Then head to the Montego Bay Cultural Centre to check out exhibits at the National Gallery West and National Museum West, which celebrate Jamaica’s rich culture. Learn about the peaceful Rastafari movement and its violent opposition in the form of the Coral Gardens incident and Bad Friday.

Pick up a few patties from Juici Patties (next door to the cultural center) to snack on as you make your way to Doctor’s Cave Beach, one of the most famous in all of Jamaica. You can spend hours here swimming, snorkeling or Jet Skiing in the pristine waters — or simply find a quiet spot in the sand and enjoy the scenic views.

Later, drive out to Scotchies for a casual (and outstanding) lunch of authentic jerk cuisine.

After your meal, head to Cinnamon Hill golf course for a leisurely afternoon on the links. Then take a tour of the Rose Hall Great House, a former plantation house that was transformed into a museum that showcases the impressive architecture of the great house while educating visitors about the devastating slave history of the estate.

As it is your last night, treat yourself to a special dinner at Marguerite’s for stunning views of the sunset reflecting off of the Caribbean. Then, head to Hip Strip, the bustling epicenter of Montego Bay, and visit one of the popular bars, such as Blue Beat Ultra Lounge for jazz, blues and stiff martinis.