Let's Get Together & Feel Alright: Jamaican Events You Simply Can't Miss

Jamaica is known for her natural beauty, vibrant culture, and friendly locals. But every year, Jamaica is also well-known for something else — can’t miss festivals. From July’s Reggae Sumfest to October’s Jamaica Food & Drink Festival, one thing is abundantly clear — Jamaicans know how to have fun. Wouldn’t you like to get in on the fun, too?

Breathtaking view of the Caribbean Sea from Aqua Bay, situated on the oceanfront at the western end of Tryall Club


Reggae Sumfest, July 19 – July 21, 2018

Off the top of your head, what is Jamaica’s most popular export? Reggae. Ever since the music was first heard in the streets of Kingston decades ago, it has taken the world by storm, spawning countless genres, deeply influencing countless others, and making the likes of Bob Marley a household name. And in Jamaica, reggae music remains as popular today as it’s ever been.

Every July, people from all over the island descend on Montego Bay to celebrate the sound of Jamaica, for an event known as Reggae Sumfest. Revered by both locals and visitors alike, Reggae Sumfest continues to thrive and adapt each year, featuring performances from some of the world's biggest stars like Ziggy Marley, Rihanna, and more.

Reggae Sumfest


Recommended Villas

Great River House, Montego Bay

Great River House

Featuring its own private saltwater pool, this 5-bedroom, 5.5-bathroom villa is close to Stush in the Bush — a local family-owned farm, serving delicious, organic, lovingly prepared farm-to-table meals daily

Calypso Shores, Montego Bay 

Calypso Shores

This charming 4-bedroom, 4-bathroom villa that includes a Hard Rock Café Beach Club membership with each rental


Jamaica Food & Drink Festival, October 28 – November 1, 2018

Jamaica is known worldwide for their distinct, often spicy (and always delicious) cuisine, coupled with their unique “island vibe,” and the Jamaica Food & Drink Festival is an annual celebration of Jamaica’s proud culinary tradition. Every October, the nation’s finest chefs — as well as foodies from all over the world — convene in Kingston for a week of eating, drinking, dancing, and reveling. Each year, the Jamaica Food & Drink Festival features several unique world-class events, held over the course of a week in iconic venues all over Kingston, creating a truly unforgettable experience for all who attend.

Jamaica Food & Drink Festival


Recommended Villas

Canoe Cove, Ocho Rios 

Canoe Cove

This contemporary 7-bedroom, 8.5-bathroom villa features a wide range of out-of-this-world amenities, including a helipad, basketball court, putting green, junior Olympic-sized pool, hot tub for up to 10 guests, and more

Seven Seas on the Beach, Ocho Rios

Seven Seas on the Beach

This fabulous 4-bedroom, 4.5-bedroom villa boasts a private pool with a slide and diving board, as well as a luxurious hot tub with a breathtaking view of the Caribbean Sea


Reggae Marathon, December 1 – 2, 2018

We’re all familiar with the Boston Marathon and the Chicago Marathon, but what about the Reggae Marathon? Well, it just happens to be Jamaica’s own famous marathon, and a marathon that can be described as VERY uniquely Jamaican. Every year, sports enthusiasts, athletes, and music-lovers unite for Jamaica's premier marathon event, characterized by energetic island vibes and lots of reggae music. Running a full marathon not your thing? This one-of-a-kind event also offers a half-marathon and 10K option, so there's an option for everyone. So log those miles and get ready for a taste of island life at the finish line.

Reggae Marathon


Recommended Villas

Almond Hill, Montego Bay

Almond Hill

This unique 4-bedroom, 4-bathroom villa features an outdoor movie projector, and each rental includes a membership to nearby Round Hill, for access to even more amenities.

Harmony Hill at Tryall Club

Harmony Hill

Located on the grounds of the legendary Tryall Club, this lavish 7-bedroom, 7.5-bedroom villa features a private heated infinity pool, as well as golf carts included with each rental.

Dying to experience one of these one-of-a-kind festivals firsthand? Browse our selection of fully staffed Jamaica villas, and start planning your escape today.