Behind the endless sandy beaches, rum-soaked cocktails and balmy nights, Jamaica has a wealth of events, festivals, cultural showcases, sporting weeks and musical regattas for visitors and guests to take part in.

Everyone who knows the Caribbean has an opinion on Jamaica. Whether you know it as the isle of silk-soft sands and azure waters, or for it’s deep cultural heritage and musical influences, this gem of the Caribbean is a tropical haven, ripe for exploring.

No matter when you travel, each month boasts a plethora of activities available for those looking for a little more than pure relaxation. We’ve highlighted some of the top on-island events for pioneers and seasoned travellers alike alongside Jamaica facts in our Jamaican Events Calendar, and encourage you to find out more at Handpicked Villas when booking your luxury villa in Jamaica.

Festivals in Jamaica


Accompong Maroon Festival
A 3 day festival celebrating the treaty at Accompong. Expect war dance reenactments, treaty songs, feasting and folk tales.
Rebel Salute Annual Festival
Annual music festival, one of the biggest in Jamaica, known for its focus on roots and conscious music. Take note – no alcohol or meat allowed.
High Mountain Coffee Road Race
Jamaica’s longest running and most challenging 10k event. A race of strength, stamina and endurance that everyone is welcome to come along and support.
Jamaica Jazz + Blues Festival
Attracting crowds of over 30,000 this amazing open air celebration of good music is held across the island, encouraging all to party!


Bob Marley’s Birthday Week
Events vary from year to year, but every occasion is designed to promote peace, happiness and ‘one love’. Visit the Bob Marley mausoleum in Ocho Rios to pay your respects.
Montego Bay Race (The Pineapple Cup)
A fast-paced adrenaline inducing boat race, set in the crystal clear waters of the stunning Montego Bay.
Misty Bliss Festival
Annual cultural festival held at Holywell (the Blue and John Crow Mountains National Park) to celebrate the designation of Jamaica’s first national park in 1993. Featuring traditional music, dance and food, as well as arts and crafts and local produce on sale.
Jamaica Fat Tyre Festival
A week long biking extravaganza that highlight’s Jamaica’s vibrant culture and awesome trails. Full of treats and heart-pounding moments this is a fantastic way to gain a new view of the island.


Spring Break
Spring Break in this beautiful retreat can be just as exciting as anywhere else in the Caribbean, or the world for that matter. Thousands of visitors travel here for the affordable parties and heaps of fun.


Jamaica Carnival
The big one. Most of the events take place on Easter Week and a lot of fun filled activity can be found in Negril and Montego Bay. Bands play reggae, calypso and soca, and everyone is filled with a positive mentality. A genuine Caribbean fiesta.
Trelawny Yam Festival
Aims to be the best showcase of history, culture and excitement that Trelawny has to offer. Many exciting activities for every age to enjoy.


Calabash International Literary Festival
A blend of songwriters, budding authors, poets and fictional dreamweaver, for those more culturally inclined.
St James Horticultural Society Annual Flower Show
Showcasing the very best of Jamaican horticultural expertise, alongside live music, stalls and refreshments. Just another example of the natural beauty of this paradise.
Jamaica Lifestyle and Wellness Festival
Endeavouring to improve local communities and boost education, this festival teaches visitors about the delicious local, healthy produce and activities that could mark the way to improved physical health.


Caribbean Fashion Week
For those with a passion for fashion, this lively week is packed with galas, designer shows, afterparties and forums for everyone to enjoy. Witness homegrown talent and stunning designs to inspire your holiday wardrobe.
Ocho Rios International Jazz Festival
Nightly jam sessions, public concerts, jazz dinners and workshops are just some of the events to look forward to during this week. Great for music enthusiasts and those looking to relax in style.
All Jamaica Grill Off
The best mass BBQ event the Caribbean has to offer. With tempting aromas of herbs, spices and hickory chips it is the ultimate mouth-watering indulgence with prizes, entertainment and a great atmosphere.


Portland Jerk Festival
Live music, wicked-hot spices and a plethora of wings, meats and veggies to try, this is the ultimate cultural event for a foodie in Jamaica.
Makka Pro Surf Contest
Held in such beautiful surroundings, with some of the best surf in the Caribbean, this sporting event is great to watch and a fantastic opportunity to pick up some tips.
Reggae Sumfest
Montego Bay’s incredible music event featuring some of the biggest names in the reggae world. This year find Wiz Khalifa, Jason Derulo, Beenie Man, Sean Paul and more big names at the line up of events.
Manchester Golf Week
A scenic and challenging course with a variety of matches and entertainments during this highlight of their golfing calendar.
Little Ochie Seafood Carnival
One of the largest and most exciting events in Jamaica. Featuring an array of succulent dishes such as curried lobster, jerk crab, fried fish, conch and much more. Truly the culinary event of the year.


Jamaica Independence Day
Every year, around the world, Jamaicans celebrate August 6th with cultural parties, dances, music, food and drink. There are plenty island-wide events for those of non-Jamaican heritage to enjoy too.
The Absolute Temptation Isle
Four consecutive days of non-stop parties on Jamaica’s most hedonistic and captivating 7-mile beach venue; Negril.
Red Stripe Dream Weekend
Concerts, water parties, mixology, dancehall, rave, all-white and more. This is truly hedonism gone crazy and for those looking for a party.
Ocho Rios Seafood Festival
A one-of-a-kind experience for those who are mad about good food. With a family oriented theme and welcome to all, this display from leading seafood chefs teaches, feeds and entertains.
International Reggae Wine Festival
For wine enthusiasts the world over, this showcase of local produce and worldwide heavyweights, couldn’t be set in a more idyllic location.


Jamaica Spice Food Festival
A one day celebration showing all Jamaica has to offer in the way of local produce. Many are for sale, or offer testers, to give you the true flavour of the Caribbean.
Miss Jamaica Grand Coronation Show
A celebration of the natural beauties found in Jamaica. The final event promises drama, excitement and atmosphere as we discover this year’s winner.


Blue Marlin Tournament
Attracting anglers worldwide to see who can catch the biggest blue marlin in late autumn.   Make sure you catch the canoe race and various parties to keep the action going for those without their sea-legs.
World Championship Dominoes
The sound of slamming fills the air, as the island has steadily become the world’s superpower in this ancient and slow-paced pursuit. Usually mixed with rum and full of passion, the heats and qualifiers make for great entertainment.


Restaurant Week
Spanning three cities, including Montego Bay and Ocho Rios, this festival gives diners more opportunities to share in the celebrate cuisine of Jamaica. Many restaurants during this time offer discounts and exciting set menus for guests to enjoy.
Jamerican Film + Music Festival
Established to celebrate diversity in front of, and behind the camera. Open to the public and a great way to immerse yourself into local culture and history.


Reggae Marathon
In the sleepy village of Negril this hardcore sporting event is great for those looking to run, and have fun! The pre-dawn Rastafarian drummers are a fantastic edition to this intense extravaganza.

Cycling In Jamaica

Remember, the extensive list above is just a taster of what’s on offer on this beautiful island. The Caribbean is all about exploration, discovery and new experiences and Jamaica has these in abundance.

To explore our villa collection in Jamaica, and to speak to one of our expert luxury villa advisors, head to Handpicked Villas, where you can contact us online, or phone us directly at +44 (0)1477 668114.

We hope our Jamaica Facts and Events Calendar have been useful, if you’d like to contribute any stories or events you think we should know about, please comment below!

Jamaica. Once you go, you know.

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