Golf Trip Dispatch: Soaking up good vibes in Jamaica

The Jamaica Invitational Pro-Am "Annie's Revenge", one of the Caribbean's best pro-ams, introduces the fun and the sun of Rose Hall near Montego Bay.
The fifth hole at Cinnamon Hill is one of the best seaside holes in Jamaica.

ROSE HALL, Jamaica — For every bogey, don't turn to some golf guru to save your game.

As my score floundered during one of the Caribbean's best pro-ams, I cranked up the sweet melodies of Jamaica's favorite son in my head.

Singin', don't worry, 'bout a thing. 'Cause every little thing, gonna be all right.
Bob Marley in "Three Little Birds"

Jamaica is best known for its reggae and ganja, but a winter golf vacation here can make you feel just as good as either one. GolfPass named Jamaica a World Top 100 Golf Destination earlier this year, one of just five Caribbean islands to make the cut (including Puerto Rico, Dominican Republic, Bahamas and Barbados). Playing any of the four premier resort courses surrounding Montego Bay will set the mood just right ... kinda like a good Marley playlist.

The Jamaica Invitational Pro-Am "Annie's Revenge" attracts many of the same teams of sun-starved golfers year after year every November. A couple celebrities, including former NFL running back Keith Byars, competed this year. You don't need a team or a pro to play. Individuals, like I was, can be paired up with others looking for partners.

There's a lot to love about the event - three rounds of golf, a beach party on opening night, a nice swag bag worth $400, on-course hospitality tents that serve local food (jerk chicken, beef patties) and drink (Red Stripe beer, Appleton Rum), afternoon beach/pool time and prizes for individual and team awards handed out at the closing gala. Golfers stay at the Iberostar Grand Rose Hall, an adults-only all-inclusive just 20 minutes from the airport. Ya mon!

The Resort at Iberostar Rose Hall

I don't know about you, but I'm a big fan of the all-inclusive experience. I think I drank more pina coladas in a four-day span than all my previous years combined. It was another way to forget my playing performance.

I've stayed in three different Iberostar resorts in the Caribbean and Mexico and never been disappointed in the food. After breakfast and lunch buffets, guests enjoy five restaurants serving a different theme every night from French, Jamaican and Italian to Japanese and Surf & Turf.

After dinner, live entertainment takes over, whether it's traditional Jamaican drums on the beach, a dancer mimicking Michael Jackson's moves in the theater or the weird-but-cool "aqua ballet" in the pool. Or you can just walk the beach like my wife and I did under a glorious full moon. It was safe and secluded.

The Iberostar Rose Hall is actually three resorts-in-one, all sharing the same beach. Those privileged enough to stay in the Grand get extra perks: butler service, free water sports (kayaks, snorkeling and paddle boards) and the opportunity to visit the other two hotels. Guests at the other properties can't invade the Grand, however.

I never left the pool after golf, but we met other couples who were more adventurous, going on a sunset cruise or a Bob Marley tour to Kingston three hours away.

Jamaica's Best Golf

The epicenter of golf on the island is Rose Hall, a former plantation with a haunting history. The pro-am is named after the legend of Annie Palmer, the "White Witch" who practiced black magic and supposedly still haunts the Great House on the hill. Palmer earned her nickname after killing multiple husbands and slaves-turned-lovers until one of them returned the favor.

Rose Hall Plantation boasts two beautiful courses - the White Witch and Cinnamon Hill. The 2021 pro-am was played on Cinnamon Hill and the nearby Half Moon Golf Course, a Robert Trent Jones Sr. classic that's flatter but no less strategic. The White Witch, a Robert von Hagge gem that's the most scenic and difficult of the three, closed early on during the 2020 pandemic for lack of play and hopes to reopen next summer.

When von Hagge tweaked the routing of Cinnamon Hill in 2001 after the building the White Witch, it became Jamaica's most fun course, bar none. One minute, you're playing golf on the Caribbean Sea. An hour later, you're lost in the jungle, staring down an elevated tee shot that drops to a green guarded by a waterfall that was filmed in a James Bond movie. Unmarked slave graves, a house once owned by Johnny Cash and ancient stone remnants of an aqueduct just add more flavor.

Montego Bay, Saint James
Rose Hall, Saint James
Montego Bay, Saint James
Montego Bay, Saint James

If you want to check off the full Jamaican golf bucket list, add a tee time at the Tryall Club. It's a 45-minute ride to play another seaside stunner that has ties to the PGA and LPGA tours. Caddies are included in all of these rounds, so don't forget tip money. While caddies should be tipped with at least one $20 bill, bring a handful of $5s and $10s to share with someone else at the resort, course or airport who makes your day. Every local we met was warm and welcoming.

There are other courses on the island, but none as celebrated as this fab four. I'm told there are plans to build two more courses - one along the same tourist corridor as the Iberostar and another in Ocho Rios - but I'd guess they're a decade away from coming to fruition, if ever. The truth is nobody comes to Jamaica solely for the golf. It's just an excuse to visit and savor the island's endless good vibes.

One love, one heart. Let's get together and feel all right
Bob Marley in "One Love/People Get Ready"
7 Min Read
February 18, 2021
If you could play golf this winter, which island would you tee it up on? Hawaii? The Bahamas? Jamaica? Bermuda? Jason Scott Deegan reveals a dozen of his favorite island escapes in winter.

Jason Scott Deegan has reviewed and photographed more than 1,000 courses and written about golf destinations in 20 countries for some of the industry's biggest publications. His work has been honored by the Golf Writer's Association of America and the Michigan Press Association. Follow him on Instagram at @jasondeegangolfpass and Twitter at @WorldGolfer.
Commented on

Played White Witch many years ago and WOW it was awesome !!!

More from the author
3 Min Read
January 23, 2023
The new course will complement the redesigned Cabot Barrens and Cabot Oaks courses that will open in December north of Tampa.
5 Min Read
January 23, 2023
Chase the game's biggest events, plus a coveted collection of new and renovated courses, to experience your next great golf adventure.
4 Min Read
January 12, 2023
Course and resort renovations, technology advancements and more are waiting in Arizona's Sonoran desert in the Valley of the Sun.
3 Min Read
January 10, 2023
The January GolfPass Gear Report shares profiles of new TaylorMade, Callaway and Srixon drivers and woods, Cleveland Golf wedges and more.
6 Min Read
January 3, 2023
Former Best Buy CEO Richard Schulze is putting his heart AND wallet behind improving not only the resort but the island as well.
1 Min Read
December 19, 2022
From the destruction of a golf resort to an our annual 'top 100' list, these articles moved the needle for our discerning readers this year.
19 Images
January 3, 2023
Austin's a hub of innovation, and the perfect place to launch Driftwood, which feels like the country club of the future.
1 Min Read
January 17, 2023
Our community of reviewers select the local favorites and hidden gems on the Emerald Isle.
1 Min Read
January 17, 2023
Our community of reviewers showcase the best public golf courses in Pennsylvania.
By Golfers' Choice
1 Min Read
January 17, 2023
These are Virginia's best public golf courses according to our community of reviewers.
By Golfers' Choice
Now Reading
Golf Trip Dispatch: Soaking up good vibes in Jamaica