5 Largest Cities In The Caribbean

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Not all cities in the Caribbean are small.  Some are actually quite large in size and population with millions of people living and working in them.  These large cities in the Caribbean region offer up the ability for visitors to take city break along with spending time lounging on a beautiful beach.   With that in mind, below I highlight the five largest cities in the Caribbean, all worthy of consideration for your next vacation.

1. Santo Domingo, Dominican Republic
Population: approximately 3,658,648

There’s plenty to see and do in Santo Domingo, the largest city in the Caribbean and Central America region. Start off with a visit to the Colonial City, a walkable grid of 16 streets recognized by UNESCO as a World Heritage Site. Here, you will find architecture ranging from the 16th to early 20th century with cobblestone lanes and iron street lamps that line the path. In addition to museums like Museo de las Casas Reales (Museum of the Royal Houses) and Museo del Arte Moderno (Museum of Modern Art), there are many restaurants and bars that offer a taste of the local culture. Santo Domingo is also a shopping haven with a string of malls that sell everything from designer clothing to leather handbags.

Dominican Republic: View of capital city, Santo Domingo. Photo Credit: © Yakov / Adobe Stock. Dominican Republic: View of capital city, Santo Domingo. Photo Credit: © Yakov / Adobe Stock.

2. Port-Au-Prince, Haiti
Population: approximately 2,618,894
Recovery from the 2010 earthquake has been slow but that doesn’t mean that Port-au-Prince is lying in ruins. Life has returned to this bustling city and the sound of pulsating music and vendors peddling their wares are welcome signs of the vibrancy of this resilient city. The hub of economic activity in Haiti, Port-au-Prince offers visitors a front row seat to the local culture with restaurants, cafes and plenty of entertainment choices.  Popular tourist attractions in and around Port-Au-Prince include Grand Rue Artists, Musée du Panthéon National Haïtien, and the Barbancourt Rum Distillery.

Haiti: Bronze statute in Port-Au-Prince titled Le Marron Inconnu de Saint-Domingue aka The Unknown Slave. Photo Credit: © Tourism Republic of Haiti. Haiti: Bronze statute in Port-Au-Prince titled Le Marron Inconnu de Saint-Domingue aka The Unknown Slave. Photo Credit: © Tourism Republic of Haiti.

3. San Juan, Puerto Rico
Population: approximately 2,196,538

A colorful array of colonial architecture and numerous attractions is what makes San Juan truly a tourist’s dream. The city is a delightful mix of old world charm along with modern boutiques that sell top brands such as Gucci, Louis Vuitton, and Ferragamo. Add to that the restaurants of Condado, the irresistible beaches and a sizzling nightlife with casinos that stay open until you say when. With so much to see and do, San Juan attracts an eclectic mix of adventurers, shopaholics and everyone in between.

Puerto Rico: Evening view on old San Juan. Photo Credit: © Konstantin L / Adobe Stock. Puerto Rico: Evening view on old San Juan. Photo Credit: © Konstantin L / Adobe Stock.

4. Havana, Cuba
Population: approximately 2,117,625

Despite being closed off to the outside world for nearly five decades, Havana is a thriving metropolis that at first glance appears like someplace stuck in the 1950s. The old buildings and classic cars bring a charm that is unique to this bustling city. As well as being the seat of government, this urban center offers shopping, history and most importantly, the opportunity to taste the local food in the many cafes and restaurants. Cuba’s vibrant culture can be experienced in the art galleries, theatres and performance venues. Perhaps best of all, Havana does not yet the capacity to accommodate a mass tourist influx so the city can be enjoyed without the touristy feel common to other cities.

Cuba: Panorama of Havana City, Vedado District. Photo Credit: © Fotos 593 / Adobe Stock. Cuba: Panorama of Havana City, Vedado District. Photo Credit: © Fotos 593 / Adobe Stock.

5. Kingston, Jamaica
Population: approximately 1,190,763

Jamaica’s capital and economic hub, Kingston is best known for its entertainment and nightlife. The city offers up a fusion of cultures from all around the world served up with a Jamaican flavor. In addition, Kingston offers the widest selection of restaurants anywhere on the island, and you can find nearly any cuisine from around the world. By day, visitors can tour historical sites and museums like the Bob Marley Museum, then party the night away at any of the dozens of nightclubs or street parties. A must have experience in Kingston is eating Devon House ice cream once named one of the top ice cream flavors in the world.

Jamaica: Devon House in Kingston. Photo Credit: © Jamaica Tourism Board. Jamaica: Devon House in Kingston. Photo Credit: © Jamaica Tourism Board.

So which of these cities in the Caribbean will you consider for your next vacation? Hopefully, one or more has appeal as all have numerous art galleries, museums, and historic buildings that are a great showcase of each island’s history and culture.  Plus the restaurant and nightlife scene is vibrant and let us not forget beautiful beaches.  

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Ursula Petula Barzey

Ursula Petula Barzey

Founder | Digital Content Creator at Caribbean & Co.
Ursula Petula Barzey is a digital marketing professional and Founder of Caribbean & Co. which has allowed her to reconnect with her Montserratian and Caribbean roots!
Ursula Petula Barzey

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