Our Ultimate 2 Week Jamaica Itinerary

Jamaica is where people come, as the famous musician Bob Marley sang, “to feel alright”, and after exploring the island for a few days, it’s really hard not to. I hope this 2 week Jamaica itinerary will help you plan your perfect vacation here be sure to check out my site for more Jamaica travel inspiration from a local.

For such a small island Jamaica packs quite a punch with the myriad activities available.  There are so many things to do in Jamaica; it’s hard to squeeze everything into two weeks.  Our Jamaica itinerary covers a few of my favourite spots. However, consider it a small sample of what the country has to offer, and hopefully it will tempt you to return for more.

My 2 Week Jamaica Itinerary

Montego Bay – Day 1 to 2

Montego Bay is the island’s tourism capital and the ideal place to start your trip to Jamaica.  Sangsters International Airport, the most usual entry point to the island, is around five minutes from the town centre, so you can be on the beach within 30 minutes of leaving the airport.

Where to Stay:  Being the tourism capital, you can find accommodations to suit any budget in Montego Bay.  You’ll find all- inclusive hotels, European plan hotels, Airbnb’s, budget accommodation, and luxury villas in the hills.    

If you want an all-inclusive stay, consider the hotels along the Rose Hall corridor.  If you want a European plan hotel consider something closer to town, say for example along the Jimmy Cliff Boulevard (formerly Gloucester Avenue).  Or, if you plan to rent an Airbnb, have a look around the Freeport or Ironshore neighbourhoods.

What to Do:  Why not spend the first day hanging out on the beach soaking up the rays.  The best beach in Montego Bay is Doctors Cave beach. For the evening give Scotchies a go if you fancy casual dining.  Or for a more formal dining option, you could visit the Houseboat Grill or Sugar Mill Restaurant, both of them excellent establishments.

For your second day in Montego Bay you can visit a great house.  The two main great house attractions in Montego Bay are the Rose Hall Great House and the Greenwood Great House.  If you plan to visit just one of them, you could also fit in a bamboo rafting trip on the Martha Brae River.

Montego Bay Jamaica

my Jamaica itinerary 2019

Negril – Day 3 to 4 of Jamaica Itinerary 

Negril is located on the western side of the island around 1 ½ hours from Montego Bay. Negril is synonymous with the beach, more specifically Seven Mile beach.    The beach is lined with restaurants and resorts. Negril is known for its laid back lifestyle, so it’s a great place to spend a relaxing day or two.

Where to Stay: When selecting a hotel, the main decision you have to make is whether to stay on the beach side or the cliff side (West End).   There are a number of hotels with varying prices along the coast. The obvious advantage of staying here is that the beach is literally on your doorstep.

If you decide to select a hotel on the cliff side (West End), you won’t find any beaches, but you will have fabulous cliff views of the ocean.  And as the main beach is only five minutes away, transportation can easily be arranged at a reasonable price.

What to Do:   For your first day in Negril, what could be better than to really soak in the vibe of Negril beach?  You can simply hang out on the golden sand and ponder those difficult decisions in life: what to drink, when to eat, and when to swim.  

Negril beach Jamaica

If you are feeling more energetic, there are numerous water sports on offer.   In the evening you mustn’t miss the famous Negril sunset. The best place to be is Ricks Café on the West End. An added plus is you get to watch the fearless cliff divers.

For your second day, why not take a day trip inland and see a different side of the island.  If you are looking for a waterfall attraction, Mayfield Falls is a personal favourite. The drive is a bit bumpy, but you get to see some of the beautiful Jamaican countryside.   

Another idea is to take in a farm-to-table experience. Zimbali Culinary Retreats, located in the hills of Westmoreland, offer such an experience.  

South Coast – Day 5 to 7 of Jamaica Itinerary 

The south coast of the island is known as the bread basket of Jamaica due to the large number of farms located in this region and is a must visit on any 2 week Jamaica itinerary.

Most visitors tend to stay on the northern coast of the island and few tend to venture to the south coast, and that is actually part of its charm.  It has not been spoiled by mass tourism. You can spend the day with a farmer while he tends his crops, or if you prefer, you can even take a trip out to sea with one of the local fishermen.

Where to stay:  Treasure Beach is the perfect base to explore the south coast of the island.   It is a laid back fishing community that personifies the no problem vibe Jamaica is known for.  You can explore hidden private coves or hang out at the beach shack restaurants waiting for fishermen to bring in the catch of the day.  

There are no high rise buildings here; instead expect to see quirky beach-side accommodations.  The most popular place to stay is Jakes Hotel. Alternatively, you can find a lot of options on Airbnb that range from high end to budget accommodations.

What to Do:   For your first day you can visit YS Falls and the Appleton Rum Factory.   Jamaica has over 120 rivers so you’d expect us to have a lot of waterfall attractions.   YS Falls is one of the most beautiful waterfall attractions. It is a seven tiered waterfall, with each fall leading into a natural swimming hole.  

apple rum factory Jamaica

If you want an adrenaline rush, try the rope swings that lead into the natural pools.  And if this is a bit too sedate and you require an extra adrenaline rush, take the zip line that runs above the waterfalls.   

Nearby you have the Appleton Rum factory the manufacturers of the world famous Appleton Jamaican Rum.   You can learn about the rum making process. You get to sample the product at various stages of production.  But the grand finale, of course, is the tasting room at the end where you get to sample the finished product.  

On your second day on the south coast, you can visit the Black River area.  There you can take a boat up the Black River, one of the longest navigable rivers in Jamaica.  You will be able to observe the endangered American crocodile as well as over 100 species of birds in their natural habitat.  

In the afternoon you can visit one of the coolest bars in Jamaica, Floyds Pelican Bar.  The bar, constructed from driftwood, is located around a quarter mile offshore on a sand bank.  The only way to get there is by boat.

For your third day you might want to take it easy.  You can relax on the golden sand beach doing absolutely nothing or go on an excursion with one of the local fishermen where you can explore a secluded beach cove.  Alternatively, you can tour a local farm and see where all that delicious local produce you have been consuming for the past few days was grown.

A special way to end your day is at lovers leap.  This is one of the most scenic spots in Jamaica, and is reputed to be the place where two star crossed lovers jumped to their death rather than be separated by a jealous plantation owner.    

The area has been reborn as a local attraction with a restaurant on site where you can enjoy the panoramic views and the beautiful Jamaican sunset.  If you go on a Sunday, there is live music, so be prepared to party.

Kingston – Day 8 to 9

Kingston is the heartbeat and capital of Jamaica.  It is also the cultural capital of the island. If you are a reggae music fan, it is definitely worth a visit.  

Where to stay:  The majority of hotels in Jamaica are located in the New Kingston area.  This is a very central location if you plan to explore the city. If you plan to rent an Airbnb, you can try the following neighbourhoods: Liguanea, Barbican, Millsborough, Manor Park, or Norbrook.

What to Do:  On your first day in Kingston, you can visit the Bob Marley Museum and Devon House. These two attractions are in close proximity to each other.    The Bob Marley Museum was the home and recording studio of reggae superstar Bob Marley. You will not only learn about Bob’s life in Kingston, but also about the Rastafarian and political history of Jamaica.   

port royal Jamaica

Your second stop for the day will be Devon House, which is located around five minutes away.  Devon House was the former home of George Stiebel, the first black millionaire in the Caribbean.   The home has been restored and it gives you some insight into Jamaica’s history. There is a courtyard at the back that offers food.  My favourite shop is the bakery that offers the famous Jamaican patty; a personal favourite is the lobster patty.

For your second day in Kingston you can visit the National Art Gallery in downtown Kingston.  If you go on the last Sunday of the month, entrance fee is free. From there you can head out to Port Royal.   This sleepy fishing village was once known as the pirate capital of the Caribbean and the wickedest city in the world, before it was destroyed by an earthquake in 1692.   Remnants of Port Royal still exist today and it provides a great insight into Jamaica’s pirate history.

After a sightseeing morning, you can have lunch at Gloria’s, a favourite seafood spot amongst locals.  If you don’t mind the drive up into the mountains, you can have dinner at Strawberry Hill. Try and get there before sunset so you can enjoy the gorgeous views of the city below.

Port Antonio – Day 10 to 12

If the idea of lush mountains and waterfalls leading down to the sea appeals to you, you will love Port Antonio.  This is one of the prettiest areas in Jamaica, but it does not get many visitors. Ironically, however, it was the birthplace of tourism on the island, but other areas such as Ocho Rios, Montego Bay and Negril have now taken that crown.    Port Antonio has a timeless, untouched, tranquil charm that makes it the perfect place to unwind.

Where to Stay: Don’t expect to find all-inclusive hotels here. Instead expect to see Eco-tourism friendly hotels like the Hotel Mockingbird Hill or the higher end but chic, stylish and laid-back Gee Jam or Trident Hotel.   There are also a number of villas for rent in the San San area if you find a villa more appealing.

What to Do:  For your first day in Port Antonio you can visit Reach Falls, one of Jamaica’s hidden gems.  Here you will find a 30-foot waterfall that cascades into several pools surrounded by a rainforest.  On your way back into Port Antonio, you can stop at the Blue Lagoon. This turquoise blue lagoon is around 200 feet deep and is surrounded by lush vegetatio – and is know as a true hidden gem in Jamaica.   

blue lagoon Jamaica

Getting hungry? Why not stop at the Boston Jerk Center to try some Jerked meat.  Boston Jerk is the home of Jerk in Jamaica and you haven’t had true Jerked meat until you have eaten there.  

The nearby Boston Bay Beach is a nice place to spend the rest of the day. It should also be noted that this is one of the few beaches in Jamaica where you can go surfing.  So if you are so inclined, you can rent a surf board.

jerk chicken Jamaica

For your second day, why not leave the coastline for a while and head up into the mountains.   There are a number of activities for you. You can go bird watching, hiking, or biking. You can also visit a coffee plantation and learn how the world famous Blue Mountain coffee is produced.

For your final day in Port Antonio, take a rafting trip down the Rio Grande.  Rafts were first used to transport agricultural produce from the hinterlands to the coastline.   It eventually evolved into a popular tourist attraction. Rafting on the Rio Grande will take you through the picturesque Rio Grande valley.  

You can spend the rest of the day at Frenchman’s Cove Beach.  Frenchman’s Cove has a river leading onto the beach, making it one of the most picturesque beaches in Jamaica.  

rafting in Jamaica

Ocho Rios – Day 13 to 14

Ocho Rios was originally a sleepy fishing village. Today it is one of the main tourist centers in Jamaica and also a major cruise ship port.  It is also the home of the famous Dunns River Falls attraction.

Where to stay:  Ocho Rios has a myriad of choices when it comes to accommodation.  You have access to budget hostels, seaside villas and if you are so inclined, a large number of all-inclusive hotels.

What to Do:  The main attraction in Ocho Rios is Dunns River Falls f and a visit is definitely recommended. It is one of the most beautiful waterfall attractions in Jamaica.  The only problem is it can get very crowded so try and visit in the early morning and definitely avoid cruise ship days.

If you want an attraction that is a bit off the beaten path, visit the Blue Hole in the hills of St. Ann, around 20 minutes outside the town of Ocho Rios.   

For your second day in Ocho Rios you can do one or more of the many activities available.  You can spend the day horseback riding in the ocean, swimming with dolphins, bobsledding and zip lining, visiting some of the other waterfall attractions, or simply enjoying a farm-to-table culinary tour.  The choices are endless.

waterfall south Jamaica

Getting around Jamaica:

If you are traveling between towns, the most economical and comfortable method is the Knutsford Express bus service.   If you don’t want to stick to a bus schedule, you can hire a private driver. Your hotel can organize this for you. If you are traveling within the town, it is best to hire a driver.   If you are traveling in Kingston it is cheaper to call a taxi company for transportation.

Safety in Jamaica

Jamaica tends to have a bit of a reputation when it comes to safety.  If you take the same precautions you would take in your home country, you should be fine.  However, here a few things to keep in mind:

  • Avoid using route taxis. Use transportation providers recommended by the hotel.

  • Avoid traveling at night, especially if you  are planning to rent a car.

  • Do not carry expensive items with you.

  • Ask locals about the areas you plan to visit.

  • Do not travel with large amounts of cash.

  • Do not use ATMs in isolated areas.

Travel Tips for Jamaica

Here are a few travel tips that should make your trip run a bit more smoothly:

  • Shop where the locals shop, the prices are much cheaper.

  • Use cambios to exchange your foreign currency.

  • If you have electrical equipment, 110-120 volts is standard in Jamaica.

  • If you are using a GPS, stick to the main roads even if the route looks shorter.   The interior roads in Jamaica tend to be winding and very narrow.

  • Make sure your phone is unlocked.  You can buy a SIM card for around US $4.

  • Use the Knutsford Express to travel between towns.

Approximate Driving Times

Montego Bay to Negril:  1 ½ hours

Negril to Treasure Beach:  2 hours

Treasure Beach to Kingston:  2 ½ hours

Kingston to Port Antonio:  2 hours

Port Antonio to Ocho Rios:  2 hours

Ocho Rios to Montego Bay:  1 hour 40 minutes

Budget for Jamaica 

  • Food : US$5 – US$20 per a meal

  • Transportation (Knutsford Express) : US $13 – US $33

  • Private Transportation: Prices vary depending on distance travelled and are usually negotiable.

  • Entrance Fee for Tours : US $20  and up

Events to look out for

  • Rebel Salute (Reggae Concert):  January

  • Maroon Festival:  January

  • Reggae Month: February

  • Carnival Celebrations: March and April

  • Jakes Triathlon:  April

  • Reggae Sumfest (Reggae Concert):  July

  • Independence Day Celebrations:  August

  • Reggae Marathon :  December

Author Bio: Charmaine loves exploring her home country Jamaica and sharing her new finds with others, especially when she finds those hidden gems.  You can leaRrn more about Jamaica on her blog at www.jamaicatravelsaver.com

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Scroll to Top