Sign In
The Unmissable Events And Festivals In The Caribbean
Save to wishlist

The Unmissable Events And Festivals In The Caribbean

Picture of Patrick Norrie
Updated: 15 November 2016
An obvious reason to go to a festival in the Caribbean is because it is almost guaranteed that it will be located within outrageously beautiful surroundings. However, these fantastic festivals deserve to be attended based on its own merit. Across the Caribbean, there are many joyful festivals fully deserving of recommendation.

the trinidad+tobago film festival

MovieMaker, an important film magazine based in America, bestowed ttff as one of the 25 coolest film festivals in the world. At the very core of ttff’s project is to reach out to its local communities: carefully selecting films that will specifically resonate with the Caribbean population. This inclusive festival will be supplemented with workshops, seminars, panel discussion and networking events. Ultimately, ttff’s work to enable greater visibility of the Caribbean film industry should be applauded.

Crop Over

Crop Over is an integral part of the cultural calendar in Barbados. This delightful, celebratory event is steeped in history: originating from when plantation workers in the 19th century broke out into jubilation once the sugar crop harvest ended. Nowadays the festival represents contemporary Barbados, while simultaneously paying tribute to its heritage. Last year’s festivities featured visual art exhibitions, markets and live music ranging from soca to folk as well as a calypso competition. Crop Over always climaxes with the ultimate colourful street parade known as Grand Kadooment.

St. Patrick’s Day in Montserrat

A pocket of Ireland can be found in the Caribbean, on a Western Indian island called Montserrat. Ireland and Montserrat happen to be inextricably linked, owing to a seismic event in the 17th Century: Oliver Cromwell’s conquest of Ireland. The consequence of this was the beginning of the Irish slave trade, with many expelled to the West Indies. Simultaneously, African slaves were also being imported by colonialists to work in Montserrat. Therefore, St. Patrick’s Day is a significant event in this small island’s history.

Chronixx live at Reggae Sumfest 2013 I (c) Beaver on the Beats/Flickr
Chronixx live at Reggae Sumfest 2013 I | © Beaver on the Beats/Flickr

Reggae Sumfest

Jamaica is the home of reggae, so it is only fitting that the country hosts what is proclaimed as the ‘Greatest Reggae Show On Earth’. For 23 years, disciples of reggae have been flocking to this festival at Montego Bay. Last year, a beach party – featuring Crazy Neil and DJ Nicco – kicked proceedings off and was then followed by All White Party and Dancehall Nights showcasing the best in contemporary reggae. If that wasn’t enough, the International Nights – headlined by Beenie Man, Sean Paul and Wiz Khalifa last year – whipped the crowd into a frenzy.

Reggae Sumfest, Catherine Hall Entertainment Center, Montego Bay, Jamaica

Curacao North Sea Jazz Festival

The sixth edition of this popular festival – located at the sumptuous Picscadera Bay Resort – will begin in style with a free event featuring two major names in Latin America contemporary music: Venezuelan salsa musician Oscar D’León and Colombian solo artist Juanes. They have yet to announce the rest of the lineup, however the pedigree showcased on previous lineups such as Prince in 2013 and Bruno Mars in 2014, only heightens the expectations. The organisers have also announced a new project: a 3 day festival for connoisseurs of Blues music.

Curacao North Sea Jazz Festival, Piscadera Bay Resort, Willemstad, Curacao

11th Havana Biennial I (c) Diaspora Vibe/Flickr
11th Havana Biennial I | © Diaspora Vibe/Flickr


Trinidad and Tobago’s annual literary festival, Bocas Lit Fest was founded in 2010, and provides a significant space in the calendar to champion Caribbean writers. The festival also offers the local population a forum to celebrate literature and meet international writers. The week is packed with activities from book signings and film screenings to music and storytelling events for children.


Junkanoo has become a major source of tourism in the Bahamas. There is now a Junkanoo Carnvial Festival taking place on May 7-9th along with the Junkanoo Summer Festival during June and July in various towns across the Bahamas. Undoubtedly, the most significant dates are the legendary Boxing Day and New Year’s Day Junkanoo in downtown Nassau. The procession is truly a sight to behold: a street of exuberant dancers, supported by musicians playing goatskin drums, horns, whistles and cowbell.

St. Kitts Music Festival

St. Kitts hosts one of the best annual music festivals in the Caribbean. Festival-goers have lauded the natural beauty of St. Kitts as being the perfect location for a musically-rich three day festival. Last year, the highlights of the lineup included the highly acclaimed calypso artist Explainer and soca musician Skinny Fabulous as well as former Destiny’s Child member Kelly Rowland.

St. Kitts Music Festival, Warner Park, Basseterre, Saint Kitts and Nevis

Grenada Carnival – Spice Mas Festival

This event’s unfettered ebullience has put Grenada on the map. The organizers work hard to build up the anticipation for the Grenada Carnival, with events such as calypso and soca competitions leading up to it. Yet the carnival – also known as Spice Mas – officially begins with the J’ouvert, early in the morning on the 10th of August, when the ‘Jab Jab dancers’ take to the streets. They are covered in bright colours or mud and wear horned helmets, dancing to calypso music and to steel band as they splash paint on bystanders. The street party carries on relentlessly throughout Monday night and the whole of Tuesday the next day.