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Sample Jamaica Trip Itineraries

Updated: May 21, 2023



Jamaica is a Caribbean Island steeped in history and culture and beauty that welcomes just over 4 million visitors each year. With the national motto of “Out of Many, One People” and unofficial motto of “One Love” you can expect to be welcomed warmly.


Journey through the country’s six unique areas with me and discover which one might be the best fit for your next vacation.


• Kingston, the capital city, is known for its a mix of night life, gastronomy, art, and music. But Kingston is most famous for its birth of reggae music which is celebrated every February and the city has the most recording studios per square capita in the world. It further received recognition in 2015 when Kingston was named a UNESCO Creative City of Music. Before you enjoy the fetes, or parties, each night, be sure to check out the Bob Marley Museum. For those that like to enjoy the culture through cuisine, plan a visit around the Blue Mountain Culinary Trail. This trail is a combination of about 15 eateries, coffee farms and mountain views. After a perfect lunch, consider stopping into the National Gallery to enjoy Jamaican art. This museum is the largest public art museum in the English-speaking Caribbean.


• Port Antonio is defined by nature and is locally referred to affectionately as “Portie.” Through its rains and lush greenery, it was established for its coconut and banana exports along its rivers. This is also where much of Jamaica’s history with the Maroons began, the descendants of escaped slaves who established free communities in the mountains. You can learn more about their history at the Charles Town Museum and Asafu Yard. The ideal place to ponder all that history is on a boat tour to the Blue Lagoon. This magnificent lagoon is breathtaking with its perfect blue color caused by its near 200-foot depth. Another beautiful Instagram-worthy spot is Reach Falls on Driver’s River. The adventurous surfer staying in the quaint town can enjoy the waves off Long Bay Beach.


• Ocho Rios is where most of the adventure options are located between the Caribbean Sea and the Blue Mountains. Bob Marley fans can participate in a tour of Nine Mile, the small village where he was both born and buried. The active traveler can zipline or bobsled down Mystic Mountain. The curious can go underground to see the Green Grotto Caves full of hidden waterfalls, stalagmites, and stalactites. This cave was even once used as hideouts by Spaniards and then by smugglers running arms to Cuba. The must-do activity in Ocho Rios is to climb the famous Dunn’s River Falls. Form a human chain to help each other up the falls before you relax for the afternoon.


Montego Bay is the resort city set by the sea. Some call it Mo Bay for short. This is the area most known to visitors looking for a great all-inclusive resort with the white sandy beach or a great golf course. You can enjoy great history when you visit the Rose Hall Great House where infamous Annie Palmer lived to torture her husbands and slaves, Johnny Cash fans can visit his home at Cinnamon Hill Great House, and swing by Sam Sharpe Square to see the statue of the man that helped lead the Christmas Rebellion of 1831 to fight for slaves’ freedom. For those that are looking for a simple, relaxing way to connect with nature, a ride down

the Martha Brae River on a guided bamboo raft may be the perfect activity.


• Negril, on the western tip of the island is where people go for romance and relaxation. This area became a popular place for backpackers and hippies to visit beginning in the 1960s and their lifestyle stuck around the area for decades to follow. Negril is home to the famous Seven Mile Beach which offers the quintessential white sandy beach and clear water. Lovers can enjoy the perfect island sunset on the west end cliffs after you sometimes find cliff jumpers there performing jumps from eight to forty feet. And the more adventurous visitors can cliff jump too. This is also the best place in the island to plan your scuba, snorkel, and deep-sea fishing excursions.


• South Coast is the most low-key section of the island and is considered to be “off the beaten path.” Consider this part of the island if you want to disconnect from the hustle of everyday life. South Coast is mostly defined by its mountains and quaint villages. And these villages work hard to protect their wildlife with the Galleon Fish Sanctuary and Fonthill Beach Park and Wildlife Sanctuary. Connect with wildlife on a safari tour on the Black River or enjoy seven different cascading waterfalls in the YS Falls.


Jamaica is an island easily accessible by air or cruise ship and has so much to offer that this island will not disappoint. You could have a great 10-night vacation that covers each of the six distinct areas. Prefer a long weekend getaway that focuses on just one? I would love to help you determine which area best fits your travel style.


Jamaica has a little bit of everything to enjoy – great weather, things to do, resorts, beaches, etc. Feel free to change up the below sequence of activities.


Day 1

Catch an early flight to Sangster International Airport (MBJ) and make your way to your private ground transportation that will take you to your 4-diamond ranked all-inclusive resort. Enjoy the afternoon exploring your resort and getting settled. End the night with a leisurely dinner and drink at one of the resort's included restaurants.


Day 2

After an early breakfast at the resort, it’s time to explore off property! Spend the day taking in some of Montego Bay’s history and architec- ture with a tour of Rose Hall Great House or Johnny Cash’s Cinnamon Hill Great House. And swing by Sam Sharpe Square to see his statue and learn about the Christmas rebellion of 1831. Upon return, grab some quick pool time before getting ready for dinner and some eve- ning entertainment.


Day 3

Today is all about relaxation! Plan for a leisurely morning with a relaxed sit-down breakfast. Then for the remainder of the day lounge in a ca- bana on the beach with butler service. In the evening after dinner, be sure to catch some of your resort’s included entertainment and dance the night away.


Day 4

Grab your breakfast to-go and hit the road! Take a day trip to Rafter’s Village and enjoy a relaxing excursion that sails you down the Martha Brae River on a bamboo raft as your guide tells you stories of the area’s history. After returning to the resort, spend some time relaxing by the pool, visiting the spa or enjoying some daytime entertainment. Grab an early dinner because tomorrow you’ll have another early start.


Day 5

You’ll be spending another day off site, so have an early sit-down break- fast, if time allows, or grab something and go! Enjoy a day trip to Ocho Rios that includes a catamaran boat ride on the Caribbean Sea for

great snorkeling before climbing Dunn’s River Falls. Make new friends as you link hands to form a human rope to help each other to the top of the falls. Spend your afternoon relaxing at your resort before heading to a late dinner. If you’re feeling up for it, grab a late-night cocktail at one of the many lounges.


Day 6

Today is your last full day in paradise and it’ll be spent enjoying all that your resort has to offer. Spend another day in a cabana on the beach with butler service. Cool off with a relaxing swim in the ocean or if you’re looking for something a little more active, grab some snorkel gear, a kayak or stand-up paddle. You’ll end with a special dinner on the beach.


Day 7

Relax with a leisurely breakfast before you head to the airport for your flight home. Please remember to allow plenty of time for traffic, bag- gage check and security lines.



Jamaica is the perfect place for families, lovers and everyone in between. When you're ready to book your Jamaican. Getaway we hope you'll reach out to us. Click here to learn more about how to work with us.

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