Want to feel like a PGA Tour pro in paradise? Annie’s Revenge Jamaica Pro-Am is for you

The Annie’s Revenge Jamaica Pro-Am hosts amateurs and PGA of America pros every year, and it’s an event every golfer should consider.

You don’t have to worry about a thing when playing in the Annie’s Revenge Jamaica Pro-Am. Because every little thing — from accommodations to dining to the tournament itself — is better than alright, it’s fantastic.

Given that you play three spectacular courses just east of Montego Bay, at Cinnamon Hill, Half Moon, and White Witch, you feel like a PGA Tour pro playing in paradise — not unlike what the top players in the world experience every January at The Sentry in Maui. The views of the Atlantic Ocean are stunning, while the routing of the holes through the Jamaican foothills is spectacular. The severe slopes and undulations make it seem like you are playing Kapalua too.

That said, where you stay and dine may even top the golf. Players lodge at the Iberostar Jamaica, a gorgeous beachside property located just a couple of miles down the road from the three host courses. All-inclusive breakfasts, lunches, dinners, and drinks are included too. Not many things are better than sipping a Caribbean cocktail while watching the waves gently crash at your feet. Eating seafood on the beach feels pretty good too.

But guess what even tops that?

The caddies at Annie’s Revenge.

More so than anything else, Jamaican golf prides itself on the overall caddy experience. You must have caddies accompany you, but you would not want it any other way. Two caddies, each wearing white jumpers like the ones you see at Augusta National, work for each group. All of them provide tremendous insight, knowledge, and advice about how to play a certain shot or how to read a particular putt. You will learn many things about Jamaican culture too, such as phrases, sayings, and customs. Get ready to hear a lot of, “YA MAN!” especially after you roll in a birdie putt. The caddies are also your personal cheerleaders, serving as your hypeman, just as Ted Scott is to Scottie Scheffler. Better yet, they are always smiling and happy to accompany you on your journey. They love their job, and they love meeting you, too. And maybe if you are lucky, you will see them sing:

As for the tournament itself, it’s unlike the PGA Tour even though you feel like a pro when you play in it. Annie’s Revenge is 54 holes and features a unique format. Each player is part of a four-man team that includes one PGA of America professional and three amateur players. The three amateurs must have an official and legitimate USGA Handicap Index to participate. That’s because two scores are counted after each hole played: the lowest gross score and the lowest net score. This allows all players of any skill level to compete while making it an inclusive experience for all. An 18-handicapper can make a five on a par-5, but that quickly turns to a net birdie thanks to that player receiving a stroke. It helps to have a balance of low handicappers and high handicappers for this reason alone. Getting strokes is crucial to the competition.

After the first 36 holes, which include one round at Cinnamon Hill and one round at White Witch, tournament organizers divide the field into four flights: Flight A, Flight B, Flight C, and Flight D. The competition then completely resets for the final 18 holes and the top three finishers in each flight receive incredible prizes courtesy of Cobra Golf, the Pro-Am’s presenting sponsor. The tournament also features closest-to-the-pin and other competitions, which produce more winners than not.

Like any player who makes the cut at a professional golf tournament, everyone heads home with a prize. You receive incredible tee gifts just for showing up, which includes a new hat, sunglasses, shoes, socks, and balls courtesy of Bridgestone. Yet, no matter how each team finished, everyone leaves Jamaica with a smile far and wide, knowing a tremendous experience was had.

But how did this terrific tournament come to be?

Donnie Dawson grew up in Kingston, Jamaica, in the 1960s and 1970s, around the same time when Bob Marley rose to international superstardom. Dawson, a terrific athlete as an adolescent, played soccer against Marley numerous times in and around Kingston — something that seemed ordinary at the time but is remarkable when looking back. Like any other Jamaican growing up then, Marley’s music was the soundtrack of Dawson’s youth, and it continues to enlighten him to this day. Exodus is his favorite album.

But Jamaica was not a desirable place to visit then, which Marley’s Exodus alludes to. Violence and belligerence between multiple political parties left the country in peril. Marley was caught in the crossfire at one point, surviving an assassination attempt before recording Exodus, the most famous and popular record of his repertoire.

That’s a major reason why this album resonates so much with Dawson. It not only features a terrific soundtrack but helps Jamaicans identify with what they were going through at the time. Marley’s record also reinforces how much Dawson loves his homeland. Even though he now resides in Southern California, Dawson still has family who live in Kingston. He visits at least twice a year — sometimes more — and every time he does so, he feels at peace. No wonder he worked for the Jamaican Tourism Board for almost four decades. He is proud of where he came from and only wants to share it with the rest of the world. He is a Jamaican ambassador at heart.

Luckily, nowadays, Jamaica does not face the danger it once did. It’s an incredible island with a unique culture that embraces love, happiness, family, and faith. Constant celebrations — or “jamming” — happen all around, and you could see this on full display at Annie’s Revenge, the tournament Dawson helped create more than 15 years ago.

Jack Milko/SB Nation

A golfer at heart, Dawson originally wanted to create a celebrity tournament for television. He wanted the “Roger Clemens of the world” as his clientele, but then he met Tom Jaronski at a Pro-Am in Puerto Rico.

After working for Golf Digest throughout the 1990s, Jaronski moved to Travel + Leisure magazine in the early 2000s. At the time, Jaronski wanted to create destination travel events across the Caribbean for amateur players from all over. So he and Dawson began talking and decided to stage something similar in Jamaica.

Annie’s Revenge was born.

Dawson then connected the Ritz-Carlton hotel to the golf courses and convinced the Jamaica Tourist Board to subsidize the tournament. (Iberostar Jamaica has since become the host resort.)

Jaronski helped market it through his magazine and other connections.

Because of his extensive experience in the golf industry, Jaronski has also served as the Tournament Director since its inception. He adds up all the scores, establishes the rules, and enforces fair play. He makes the morning announcements and texts messages to all the players, reminding them of everything he said. If you have a question or an issue, you address it with Jaronski, who somehow makes himself available to any request and any player.

Together, Jaronski and Dawson do a terrific job facilitating this event, which will celebrate its 18th year in 2025.

But the biggest issue they face from now on is with mere numbers. They want more teams, more golfers, and more people to experience what Jamaica has to offer. This past November, Annie’s Revenge had 21 teams. They want 40 at their next one.

“This is a grassroots event,” Dawson said.

“It’s not a big made-for-TV thing. This is a grassroots event where we can get the pros, get players, and we say, ‘Hey, let’s entertain you and show you Jamaica.’ Everyone who comes loves it, but it’s just recruiting the amateurs to come, getting the pros at various clubs to bring their amateurs.”

Discussions are being made about whether November is an ideal time frame for Annie’s Revenge. Heading to the Caribbean right before Thanksgiving may prove difficult for some people, especially those who have to travel again for the holidays. Maybe January would work better, considering that most of the country has been blanketed by Arctic air all month. That could convince more golfers to flock to Jamaica, especially since Santa Claus brings many players clubs, bags, and countless other accessories each December. Playing is at the forefront of every player’s mind in the new year, but the problem is, where can they play?

You can certainly do so in Jamaica.

“If you’re a golfer looking for an immersive experience in Jamaica,” Jaronski said.

“Annie’s Revenge is arguably your best option.”

Indeed it is.

Now, you may ask yourself, what is the cost of playing in Annie’s Revenge?

For amateur players, it’s a shade under $4,000, which includes everything from golf to dining to everything the resort offers. It’s in line with other events like this, and frankly, it’s a terrific price considering all that it offers. It does not include airfare, but if you want a Caribbean escape and play in a tournament that makes you feel like a PGA Tour pro, then Annie’s Revenge is the perfect option. You will not regret it either, as you will have memories that will last a lifetime.

Ya, man!

Jack Milko is a golf staff writer for SB Nation’s Playing Through. Follow him on X @jack_milko.