We’re thrilled to share an exciting lineup of events that will make this year a memorable one! Whether you're looking to celebrate or simply enjoy time with friends and family, we've got something for everyone. From iconic festivals to week-long parties and sporting adventures, there's something for everyone to discover the best of Jamaica.
Looking for the inside scoop on where to stay, things to do, and where to eat? Download our free Visitor Guide!
Kingston Pirates Week: October 29-November 2, 2025
Location: Port Royal, Kingston
The Port Royal Pirates Festival is set to become one of the region's premier events, providing a hands-on, family-friendly experience that immerses attendees in the vibrant history of piracy through captivating costumes, decor, and activities. This event holds immense potential to attract both local and international audiences.
Gains & Planes: October 30-November 2, 2025
Location: Negril
Gains & Planes: The Original Fit & Lit Weekender is a first-of-its-kind 4-day festival blending high-energy fitness with unforgettable nightlife, set in the tropical paradise of Negril. This is not a retreat—it’s a movement. Expect beachside workouts by day and wild themed parties by night, with a curated schedule of 10 epic events across the long weekend. Think strength sessions, dancehall cardio and beachside boot camps, costume nights, and beach games—all designed to connect like-minded adventurers who train hard and party harder.
Powered by top DJs, trainers, and brand partners, Gains & Planes offers a fitness-meets-festival vibe like no other. Flights and hotels are booked separately, but your ticket unlocks access to the full lineup, exclusive perks, and a vibrant international community. Whether you’re coming solo or with your crew, this is your ticket to an unforgettable Halloween weekend in paradise.
4D Pirates and Wenches: November 1, 2025
Location: Hope Zoo, Kingston
Unleash your inner pirate for a cause! Come dress to impress at this adults-only pirates inspired event where spirited drinks will be in abundance as you donate to a worthy cause. Indulge in the lifestyle lived by the pirates of Port Royal and party just like they did years ago. Let’s drink and dance together!
Kingston City Run: November 2, 2025
Run for a cause, dress for the adventure! Let’s join this notable event staged for a worthy cause at the Kingston City Run where participants can partake in a 5k or 10k run, walk or wheel set to raise funds for Kingston’s most vulnerable. Come decked out in your pirates costume as part of the celebrations for Kingston Pirates Week. See you there! Let’s move with purpose, give back and have some fun doing it. See you at the start line!
Port Royal Pirates and Seafood Festival: November 2, 2025
Bring the whole crew for a day of food, fun and pirate flair! As part of Kingston Pirates Week, the Port Royal Pirates and Seafood Festival caters to patrons of all ages offering a fun-filled atmosphere of humorous live entertainment, authentic Jamaican dishes and much more. Come for the seafood, stay for the vibes; adventure awaits in Port Royal!
Treasure Beach Food, Rum & Reggae Festival: November 7 – 9, 2025
Taste the vibe, feel the rhythm, live the spirit of Jamaica! There’s no better way to experience the culture of Jamaica than through its rich flavours, music and community spirit. Set against the laid back charm of Treasure Beach located on the South Coast, the Treasure Beach Food, Rum and Reggae festival captures it all and showcases the essence of Jamaica with three (3) days of delicious authentic Jamaican food, local rum and world famous reggae music. This highly anticipated event should not be missed. Come and indulge in the fun and experience Jamaica. Come for the food, stay for the music, and leave with a heart full of Jamaica. Don’t miss it!
Jamaica Pro Am ‘Annie’s Revenge’ Golf Invitational: November 19-23, 2025
Location: Montego Bay
Golf, luxury, and endless ocean views—the Jamaica Pro Am 'Annie’s Revenge' is more than just a tournament; it’s an unforgettable experience where world-class golf meets unmatched Caribbean hospitality! Montego Bay is ready to welcome you November 19-23!
Mouttet Mile: December 6, 2025
Location: Caymanas, St. Catherine
This event is a one-mile race at Caymanas Park, which carries a total purse value of US$300,000.00, making the race day the richest in the English-speaking Caribbean. The race will feature the top 3-year-old native breeds and imported thoroughbreds, with 4 spaces reserved for international entrants. Dress to impress at this exclusive presentation of fashion, food, and rum experiences.
WAVZ 5k Beach Trot: December 6, 2025
Location: Negril
The WAVZ 5K Beach Trot is a vibrant wellness weekend featuring a scenic beach run. Participants can enjoy beach massages, volleyball, and exclusive local deals, all while celebrating Jamaican culture in a festive atmosphere.
Reggae Marathon: December 7, 2025
Location: Kingston
The Reggae Marathon & Half Marathon is Jamaica’s premier international marathon event. Marathoners, sports enthusiasts, and beginners converge in Kingston for a fun event characterized by good vibes and lots of Reggae music. Enthusiastic supporters come out along the looped, internationally certified course to support participants. The pulsating Reggae music on course also keeps participants in an “irie” spirit as they burn the mileage.
Check out our visitor's guide for must-do experiences, sights, and sounds of the island to make your time in Jamaica unforgettable.