Experience Jamaica's
Top Festivals & Events of 2019


Come Alive in Montego Bay

Montego Bay is arguably the heart of Jamaica. With its sun-filled skies, bustling hubs, and world-class amenities, it’s the ultimate gathering for those seeking the perfect blend of culture and creativity. Cool down with a delicious local cocktail seaside, or enjoy the reggae beats that Jamaica is known for. And, at all times, come alive with the island vibe.

Don’t Miss These Montego Bay Events

Pineapple Cup Yacht Race – A staple Montego Bay event since 1961, the Pineapple Cup Yacht Race is an 811 nautical mile journey that offers a challenging course, friendly competition, and some of the best sailors in the world.– Join us January 27, 2019

Reggae Sumfest – Summer sizzles in style with a twist on the classic reggae beats the islanders know and love. This 19th year of Jamaica’s premier reggae festival is sure to offer some of the biggest entertainers and events yet.– Join us July 13 – 20, 2019

Chukka-Hanover Charities Polo Event – Posh and inviting, this is your chance to join us for the world’s most prestigious polo event for a great cause! This year, experience the US Rhode Island Polo Team’s, along with local greats.– Join us February 17, 2019


Discover Negril Like Never Before

Known worldwide as one of the most beautiful Caribbean destinations, Negril offers visitors (and locals) the best of the best. Take a walk down the renowned “Seven Mile Beach,” where seven miles of white sands welcome you to paradise. Indulge in seaside Jerk Chicken, bask in the turquoise seas, or go bold, and try cliff-jumping for a true adventure.

Don’t Miss These Negril Events

Dream Weekend – Dreaming of partying in paradise? Here’s your chance! This nearly weeklong international music event is set on a perfect island backdrop offering energy, music, and more during Jamaica’s Independence holidays. – Join us August 1 – 5, 2019

Bob Marley Birthday Bash – Though this event really needs no introduction, you’re invited to an event where reggae takes center stage and artists offer classic island beats – with a twist. Discover how the King of Reggae’s soul lives on here. – Join us February 2 – 6, 2019

Reggae Marathon – Love running? Love reggae? Combine the two and take part in the one-of-a-kind Reggae Marathon where the energy, music, and friendly islanders fuel you for a sun-filled 26.2 miles unlike any other. – Join us December 8, 2019


You’re in luck. Jamaica is home to far more events than those listed here! Simply pick your pleasure, point on a map, and you’ll find some of the greatest island events in Jamaica. Here are a couple more Jamaica events coming up that you simply won’t want to miss…

Marbana – It’s no wonder this event was dubbed “The Best Party Experience During Easter Weekend.” Catering to carnival and beach-party lovers, this exclusive premier event offers an exotic location, and a fusion of music and revelry you can’t beat. – Join us April 19 – 21, 2019

Jake’s Off Road Triathlon – There’s nothing better than an athletic event…unless you put that athletic event against a pristine island backdrop. Get dirty and challenge yourself in this rugged, serene, and exciting test of stamina and will on Jamaica’s South Coast.– Join us the last Saturday of April 2019

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Door-to-Door Transportation

Want a personal driver to transport you? Your personal Concierge will coordinate the details to eliminate the hassle.

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Enjoy the VIP Ticket Lifestyle

Your personal Concierge can coordinate special VIP tickets, getting you closer than ever before to all the action – regardless of the event.

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Personalized Details

Drinks & amenities aren’t allowed at the festival, but your Concierge will have your meal and drinks ready and waiting when you want.

To learn more call and speak with our team at 301.229.4300