Best Caribbean Highlife Destinations To Visit

Cancun, Mexico

Cancun has a well-deserved reputation as a spring break destination, and that’s because it has some of the Caribbean’s most bustling nightlife spots.

San Juan, Puerto Rico

The closest place the Caribbean has to New York City. From Old San Juan to Condado, there are terrific bars and clubs to enjoy.

Santo Domingo, Dominican Republic

It’s not just the Dominican Republic’s capital — it’s the country’s nightlife capital, too. Bars, clubs, casinos, dancing and what might be the Caribbean’s most diverse live music scene.

Port of Spain, Trinidad

Port of Spain is the most developed city in the English-speaking Caribbean, and it shows. And there aren’t just a host of night spots to check out (especially in St James, the so-called “City That Never Sleeps”). There’s also Port of Spain’s famous, all-night street food.

Willemstad, Curacao

We’re big fans of many of the bars and clubs in historic Willemstad and the surrounding areas. And Willemstad is perhaps the most walkable city in the entire Caribbean.

Montego Bay, Jamaica

Much of the action here after dark is on Gloucester Avenue on what’s known as the “hip strip.” From live theatre to sports bars to jazz, you’ll find it all here.

Philipsburg, St Maarten

St Maarten has a number of seriously good bars, and, of course, a number of casinos, where you can always have a great time, no matter the hour.

Cabarete, Dominican Republic

The Caribbean’s bohemian destination never shuts off — and the best thing is, you can walk to everything, most of which is set right on the beach.

Oranjestad, Aruba

You’ll find much of the island’s nightlife in its many casinos, but bar hopping is very much alive and well here, from intimate dives to large clubs.

St Lawrence Gap, Barbados

Yes, Barbados. It’s not the first thing you think of about the island, but the St Lawrence Gap area in Christ Church has some of the best nightlife in the Caribbean — and bars that are open as much as 24 hours.