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Expat Exchange - Best Places to See While on a Look-See Trip to Jamaica (Plus, Itineraries) 2024
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Montego Bay, Jamaica

Best Places to See While on a Look-See Trip to Jamaica (Plus, Itineraries)

By Betsy Burlingame

William Russell
William Russell

Summary: Considering a move to Jamaica but uncertain about where to settle? Venturing on an exploratory trip to visit multiple popular expat destinations can be incredibly enlightening. Here's a list of recommended places to consider during your exploration of Jamaica.

Embarking on a Look-See trip to Jamaica is an essential step for anyone considering relocating to this vibrant island nation. Such a trip allows potential expats, retirees, and digital nomads to immerse themselves in the local culture, assess the living conditions, and explore various neighborhoods and communities. It's an opportunity to gather firsthand information about the cost of living, healthcare, safety, and social opportunities, which are crucial factors in making an informed decision about moving to a new country.

Recommended Itineraries

For those planning a Look-See trip to Jamaica, it's important to tailor your itinerary to explore a variety of cities, towns, and regions that are popular among expats and digital nomads. A 10-day trip could focus on the northern coast, starting in Montego Bay, then moving to Ocho Rios, and finishing in Port Antonio. For a more extensive 20-day trip, you could start in Kingston, then travel to the Blue Mountains, followed by Mandeville, Negril, Montego Bay, Ocho Rios, and finally Port Antonio, allowing for a comprehensive view of the island's diverse living options.


Kingston, the capital city of Jamaica, is a bustling metropolis that offers a mix of business opportunities, cultural experiences, and a vibrant arts scene. With a population of over half a million, Kingston is the cultural and economic heart of the island. Expats and digital nomads are drawn to its diverse neighborhoods, relatively lower cost of living compared to other global cities, and the proximity to the Blue Mountains. The city is also home to several universities, hospitals, and international schools, making it a practical choice for families.

Travel Tip: While in Kingston, visit the Bob Marley Museum, the former home of the reggae legend, to delve into the rich musical heritage of Jamaica.

Montego Bay

Montego Bay is one of Jamaica's most well-known tourist destinations, but it's also a favored spot for expats seeking a balance between resort-style living and authentic Jamaican culture. Known locally as MoBay, the city offers a range of residential options, from luxury gated communities to more modest local neighborhoods. The cost of living can vary greatly depending on the lifestyle one chooses. Montego Bay is also a gateway to other parts of the island, thanks to its international airport.

Travel Tip: Don't miss the chance to dine at The HouseBoat Grill, a unique floating restaurant offering a fusion of flavors and a memorable dining experience.

Ocho Rios

Ocho Rios, often referred to as Ochi, is a port town on the north coast known for its stunning waterfalls, lush gardens, and beautiful beaches. It's smaller and less bustling than Montego Bay, making it appealing for those looking for a more laid-back lifestyle. The town has a growing expat community, and the cost of living is moderate. Ocho Rios is also a popular spot for cruise ships, which can add a lively atmosphere to the town.

Travel Tip: Make sure to visit Dunn's River Falls, one of Jamaica's most famous natural attractions, where you can climb the cascading waterfalls or relax on the adjacent beach.

Port Antonio

Port Antonio is located on the northeastern coast of Jamaica and is known for its charming, unspoiled natural beauty. It's less commercialized than other Jamaican towns, offering a tranquil environment for those looking to escape the hustle and bustle. The cost of living here is generally lower, and the area is becoming increasingly popular with expats interested in sustainable living and eco-tourism. Port Antonio is also renowned for its stunning beaches, such as Frenchman's Cove and Blue Lagoon.

Travel Tip: Experience the local cuisine at Boston Jerk Centre, where you can savor authentic Jamaican jerk dishes in a rustic outdoor setting.


Negril is famous for its laid-back atmosphere and the stunning Seven Mile Beach, one of the most beautiful beaches in the world. It's a small town that's popular with tourists and expats alike, offering a mix of luxury resorts and local living. The cost of living in Negril can be affordable, especially if one adopts a lifestyle that embraces local goods and services. The town's relaxed vibe makes it a haven for retirees and digital nomads seeking a slower pace of life.

Travel Tip: Visit Rick's Café for its cliff-side location and spectacular sunset views, and if you're adventurous, take a leap from the famous cliff-diving spots.


Mandeville is a highland town located in the heart of Jamaica, known for its cooler climate and colonial history. It's a popular choice for expats due to its peaceful environment, relatively low crime rate, and established expat community. The cost of living is reasonable, and the town offers a variety of housing options. Mandeville is also home to several schools and healthcare facilities, making it a practical choice for families.

Travel Tip: Enjoy a meal at The Mandeville Hotel's restaurant, which offers a blend of international and local cuisine in a historic setting.

Blue Mountains

The Blue Mountains region is not a single town but an area that includes several small communities like Irish Town and Newcastle. It's renowned for its breathtaking scenery, cooler temperatures, and the world-famous Blue Mountain coffee. This region is ideal for nature lovers and those seeking a quieter, more rural lifestyle. The cost of living here can be higher due to the remote location, but the natural beauty and tranquility are unmatched.

Travel Tip: Plan a visit to the Craighton Estate for a guided tour of the coffee plantation and to sample some of the finest coffee in the world.

About the Author

Betsy Burlingame Betsy Burlingame is the Founder and President of Expat Exchange and is one of the Founders of Digital Nomad Exchange. She launched Expat Exchange in 1997 as her Master's thesis project at NYU. Prior to Expat Exchange, Betsy worked at AT&T in International and Mass Market Marketing. She graduated from Ohio Wesleyan University with a BA in International Business and German.

Some of Betsy's articles include 12 Best Places to Live in Portugal, 7 Best Places to Live in Panama and 12 Things to Know Before Moving to the Dominican Republic. Betsy loves to travel and spend time with her family. Connect with Betsy on LinkedIn.

William Russell
William Russell

William Russell
William Russell

Montego Bay, Jamaica

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