Exploring The Caribbean By Attending Carnivals, Festivals & Major Events  

Jamie-Lee Abtar

Saint Lucia Carnival Reveller

The Caribbean is known primarily for sun, sand, and sea but it is so much more than that.  With each Caribbean destination having a rich heritage and culture, there is much to experience, and this comes to life in hundreds of annual carnivals, festivals, and significant events related to culture, food, music, rum, sports, sailing, etc.  With that in mind, below are some of the best events for exploring the Caribbean during 2019 designated as the Year Of Festivals by the Caribbean Tourism Organization.

Turks & Caicos Islands – Wine Cellar Golf & Fishing Tournament

2019 Dates:  10th February – 17th February

Launched 2011, the annual Wine Cellar Gold & Fishing Tournament brings together the local Turks & Caicos community and visitors for a range of fishing and golfing events.  The emphasis is on having fun and attendees can participate in competitive and entertaining activities including a golf tournament and fishing competition along with a fresh fish auction of the day’s catch, music, entertainment, and kid-friendly games.  All proceeds from the Wine Cellar Golf & Fishing Tournament are typically donated to a local charity.

Trinidad & Tobago Carnival

2019 Dates:  4th March – 5th March

The Trinidad & Tobago was launched after the Slavery Abolition Act 1833 was passed and builds on French carnival traditions by including events emphasizing African folklore, culture, and religious traditions.   Now considered the Mother of Caribbean Carnivals, the big finale with a parade of mas bands wearing colorful costumes takes places in February or March each year on the Monday and Tuesday before the first day of Lent, which coincides with Ash Wednesday.  Leading up to this are numerous events including calypso, soca, and Panorama steel band competitions, beauty queen and traditional mas competitions along with various J’ouvert celebrations.

Montserrat St Patrick’s Festival

2019 Dates: 8th March – 18th March

Many of the early settlers on Montserrat were Irish, and so St Patrick’s Day has been celebrated on and off of this Caribbean island known as the other Emerald Isle for quite some time.   However, what Montserratians primarily celebrate today is not Saint Patrick, the first patron saint of Ireland but their African ancestors who lost their lives in the failed slave rebellion on St Patrick’s Day, 17th March 1768.  Thus, while there are lots of party-type events, there is also a strong emphasis on African and Montserratian culture and heritage during this week-long festival.

Bequia Easter Regatta

2019: 18th April – 22nd April

The Bequia Easter Regatta is one of the highlights in the Caribbean sailing season.  Held over the Easter weekend in Bequia for 35+ years, the Bequia Easter Regatta is well known for its unique blend of local double-ender racing, yacht racing, and shoreside activities.   The whole island gets caught in up in regatta fever with each race showcasing different types of boats, skill level and traditions.  On Sunday there is the  Regatta Lay Day on Lower Bay beach which sees a grand fete for boatloads of visitors to the island of Bequia.

Guyana – Rupununi Rodeo

2019 Dates: 20nd April – 21st April

Dating back to the 1960s, the Rupununi Rodeo is held annually over the Easter weekend. A highly anticipated event by local Rupununi cowboys and cowgirls as well as visitors, there is a range of competitions including popular events like bareback bronco, saddle bronco, steer roping, and wild cow milking. While it is an exciting and entertaining event; it is also a great way to learn about the history, culture, and people of the Rupununi region in Guyana.


Saint Lucia Jazz Festival

2019 Dates: 5th May – 12th May

Wanting to draw tourists to the island of Saint Lucia during May which was traditionally a slow period, the Saint Lucia Jazz Festival started in 1991 and is a showcase of local and international musicians – a careful mix of acoustical and fusion jazz with rhythm and blues.   Now 25+ years later, its considered one of the best jazz festivals in the world and a top festival in the Caribbean.

Grenada Chocolate Festival

2019 Dates:  31st May  – 7th June

The Grenada Chocolate Festival is a celebration of Caribbean cacao farmers and bean to bar chocolate producers.  Started in 2014 by Magdalena Fielden a passionate chocolate lover who also owns True Blue Bay Boutique Resort, the week-long Grenada Chocolate Festival has a series of events for festival-goers to learn about cacao farming and production including visits to local plantations.  There is also a range of activities to learn about and sample different food products currently being made from cacao and chocolate.   Getting better each year, it is a chocolate lovers paradise.

St Kitts Music Festival

2019 Dates:  26th June – 30th June

The St Kitts Music Festival is another long-standing music festival in the Caribbean.  Started in 1996, this annual musical festival typically held in June has featured a broad range of musical styles including reggae, soca, calypso, rhythm and blues, jazz, hip-hop, gospel, and contemporary music.  Previous artists have included such major acts as John Legend, Lionel Richie, Goo Goo Dolls, Wyclef Jean, The Commodores, Dionne Warwick, Billy Ocean, Stephen Marley, Jah Cure, and Beres Hammond.

Nevis Mango & Food Festival

2019 Dates: 4th July  – 7th July

Mangoes are one of the more delicious fruits eaten in the Caribbean, and they are showcased at the annual Nevis Mango & Food Festival which has a series of events hosted by international and local chefs.  The list of activities includes cooking masterclasses, celebrity chef dinners, a food lime and mango feast.  Nevis is perfect for hosting this mango food festival as over 30 different types of mangoes are grown and consumed on the island.

Tobago Heritage Festival

2019 Dates: 12th July – 1st August

The Tobago Heritage Festival held each year showcases the unique cultural traditions of Tobago.  Starting in 1986, the two-week Tobago Heritage Festival begins with an evening gala featuring a range of cultural performances including sing, dancing and spoken word acts, and folk dramas.  Then throughout the two weeks, visitors are encouraged to visit all the villages in Tobago each showcasing a different facet of Tobago culture including the re-enactment of what the locals refer to as an ‘Ole time wedding in Moriah’ (an 18th-century wedding procession through the streets of Moriah village), folklore story-telling, drama, and traditional dances.

Antigua Carnival

2019 Dates:  26th July – 6th August

The Antigua Carnival is typically held at the end of July through early August and was initially a celebration of the emancipation from slavery.   The Antigua Carnival has evolved over the years, but at its core are calypso, soca and steel band competitions.  Other significant events of the Antigua Carnival include the Parade of Bands along with the Miss Antigua Pageant and the Caribbean Queen’s Competition.  Along with the major events are numerous parties, concerts, food fairs, and cultural shows.

Curaçao Pride Week

2019 Dates: 25th September – 29th September

Most Caribbean islands are welcoming but don’t openly market to the gay and lesbian community.  One island that does is Curacao which has a “Live and Let Live” attitude and now an annual Curacao Pride Week.  Among the events held during the Curacao Pride Week, is a Pride walk from Rif Fort to Wilhelmina Plaza, a Rainbow Lounge cocktail party at Papagayo Beach Club, a “Navigaytion Sea Parade” with BlueFinn Charters and a white party at Club Spoonz.

Barbados Food & Rum Festival

2019 Dates:  17th October – 20th October

Launched in 2009, the Barbados Food & Rum Festival is a celebration of Bajan along with other Caribbean food and rum.  The four-day festival includes a range of food and rum events hosted by restaurants and celebrity chefs.   Signature events during the Barbados Food & Rum Festival include the opening festival, signature rum event, dine around at local restaurants, plus an afternoon rum and canapes at a polo match.

Dominica World Creole Music Festival

2019 Dates: 25th October – 27th October

The World Creole Music Festivals held in Dominica started in 1997 as part of the month-long celebration for Creole Month.   The goal is to advance Creole culture and music across the globe thus then as now, the focus is on featuring indigenous music including Cadence-lypso, Kompa, Zouk, Soukous, Bouyon, and Zydeco.  The lineup typically includes artists from Dominica as well as the French Antilles, Africa, and North America.

British Virgin Islands Food Fete

2019 Dates: 2nd November – 2nd December

Held each November since launching in 2014, the British Virgin Islands Food Fete offer up a range of food and restaurant events designed to showcase the food loved by BVI locals and dished from other parts of the globe infused with a Caribbean flair.   Some of the headline events typically included in this month-long celebration that appeals to foodies include the Anegada Lobster Festival, Barefoot Gourmet Soiree, Taste of Tortola and Taste of Virgin Gorda.

Cayman Islands Pirates Week Festival

2019 Dates: 7th November – 11th November

The Cayman Islands Pirates Week Festival celebrates the culture of the island as well as its pirate legends.  Held annually for the last 40+ years, the main events for the  Cayman Islands Pirates Week Festival includes street dances, competitions, food festival, two glittering parades, sporting events, fireworks, etc.  The main events are held on Grand Cayman; however, there are also events before on Cayman Brac and then after on Little Cayman, so it turns into a month-long celebration and allows for island hopping and getting to know the Cayman Islands, its people, and culture.

Jamaica Reggae Marathon

2019 Dates: 8th December

Started in 2001 by the Jamdammers running club, the Reggae Marathon held in December each year, is now one of the best in the Caribbean and the globe.   Runners from all around the world visit the island of Jamaica to run along the IAAF certified course in Negril, for the marathon and also half marathon and 10K races.   Overall, it is a fun racing event with good vibes and lots of pulsating reggae music at each mile marker.   Before the races, there is also a gourmet Pasta Party and Expo.

These are but a small sampling of the Caribbean carnivals, festivals and major events held each year.  What’s great is that most of these events are three to four days and so it leaves plenty of time to also experience some of the top attractions in each Caribbean destination.  To find other events, explore the Caribbean Destinations Calendar of Events put together by the Caribbean Tourism Organization.   Whatever your interest, you are sure to find a Caribbean event that has appeal.

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Ursula Petula Barzey is the Founder of Caribbean & Co. an award-winning digital platform and blog promoting Caribbean travel and luxury lifestyle. The website launched June 2014 provides insight on things to do, where to stay plus living and working in the Caribbean region.

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