Site logo

Jamaica: Annie’s Revenge Pro-Am

By David R. Holland

ROSE HALL, JAMAICA – Annie’s Revenge Pro-Am is many things – warm breezes, jerk chicken, Red Stripe beer, Appleton Rum, new golf buddies and island hospitality.

Montego Bay is where, each November, amateur and professional golfers, come to play and enjoy tropical vistas to the Caribbean Sea, lush hillsides and target holes prominent on Cinnamon Hill Golf Course, winding uphill and downward toward ocean-hugging holes.

Near the 15th green there’s a gentle waterfall, site of a scene in the James Bond movie Live and Let Die. You will pass the 1761 ruins of a sugar mill and aqueduct, and on another day enjoy the Half Moon Golf Course that was designed by legendary architect Robert Trent Jones, Sr. Half Moon is routed through a retired sugarcane estate, and the course hugs forested hills.

Participants of Annie’s Revenge are spoiled from airport to check-in at the Iberostar Grand Rose Hall, an adults-only all-inclusive resort. Besides three rounds of golf, attendees are presented with a Jamaica Tourism backpack and swag worth $400. We got Puma golf shoes, golf shirt, long-sleeved pullover, 12 Bridgestone golf balls, bluetooth speaker, Shady Rays sunglasses and more.

After golf, beach and pool times are built in to the afternoon schedule and the all-inclusive dining included full breakfast buffet at Port María Jamaican Restaurant in the morning, on-course drinks, breaded jerk chicken and beef snacks and evenings at restaurants Teppanyaki Kiniro, Surf and Turf Galleon, La Toscana Wine Cellar, Cornwall Buffet, Es Palau gourmet restaurant and the Beach Grill

The Golf Connection LLC., led by golf industry veteran Tom Jaronski, provided the coordination of the two courses, scoring logistics, the parties, awards and work with the Jamaican Tourist Board and major sponsors like Puma Golf, Red Stripe beer and Appleton Rum. 

Meeting my playing partners was another enjoyable highlight. How many times have you teed it up with a 6-foot-10, 295-pound golf pro? That would be once for me with Zach Ramey, Swing Coach for Next Level Golf — he couldn’t have been more fun, helpful with shot analysis and gracious. Kevin and Carol Creter completed my fun foursome. 

“The courses here, Half Moon, Cinnamon Hill, White Witch and Tryall are so different,” Ramey said. “There are no two holes alike and each have their challenges with the wind on the island that can pick up, go down, can be a benefit or be a disaster.  At the end of the day you think, man, I want another try to do better.”

Ramey, who first came to Jamaica in 2014 for the Pro-Am, said:  “The hospitality is always warm. Annie’s Revenge, from start to finish, is so enjoyable and Tom Jaronski is always there to address any questions. I travel around to many mini-tour events and tour qualifiers as a professional and you don’t always get great communication, but here is is clear cut what’s going on 24-7.”

So what’s the story behind the pro-am’s name? The Rose Hall Great House is a former plantation headquarters and Annie Palmer, who lived there, became known as the “White Witch” as she terrorized her slaves. She was accused of killing three husbands, using black magic, and contrary to rumors she was not murdered.  Legend has her haunting the grounds.

Here’s a snapshot of the two golf courses we played:


History follows you along your journey here. On the second tee you swing toward the Rose Hall Great House. Off the fourth tee box is a centuries-old cemetery for the family of English poet Elizabeth Barrett Browning. Here, also, is The Cinnamon Hill Great House, built in 1734 by Edward Barrett, ancestor of the poet, and the second home of Johnny Cash and June Carter Cash for 30 years. 

Photo ops include an ancient aqueduct used to grind sugar cane in the plantation era. Upon close inspection of the supporting pillars, players can see the year of construction, 1761. 

There’s 400 acres of fun at Cinnamon Hill, a par-72, 6,828 yards, starting in an open, wind-swept front nine that features two holes on the turquoise Caribbean Sea. 

The Robert Von Hagge 2001 redesign morphs in to a back-nine with dense foliage and target golf. 

The signature hole, Majestic Blue, is the fifth, a 453-yard par 4, slopes gently and the fairway fades into the aquamarine sea. It’s the best hole in Jamaica say many golf enthusiasts. The sixth hole is a par-3, 168-yarder over the sea with a bunker guarding.


Open in 1962 by Jones, Sr., the course was modernized by Roger Rulewich, who removed non-native trees and and renovated bunkers, creating a fun track routed through a retired sugarcane estate in the foothills of the western Jamaican coastline. The best caddies are found here. 

It’s a par-72, 7,141-yard traditional classic with lots of chances to dodge countless shallow-faced bunkers and is very walkable. Constant trade winds blowing off the Caribbean Sea create up-wind challenges and down-wind opportunities.

Half Moon has hosted a number of prestigious tournaments including the Jamaica Open Golf Championship, the Dunhill Cup Final of the Americas, and the Red Stripe Pro-Am. 


This beachfront, adults-only, all-inclusive hotel on Montego Bay provides butler service, and a variety of amenities right down to the pillows, which can be chosen nightly from the pillow menu. Sea and garden views are available from 189 of the rooms, while 104 rooms have direct beach access. 

One can also be spoiled with a treatment from Spa Sensations. An offering of individual or couples treatments, massages, and therapies by the Caribbean staff are performed. Opt for in-house or seaside services. Turkish and Roman baths, jacuzzis, thalassotherapy pools, and suites for private treatments are also available.

Every day at the Iberostar Grand Rose Hall is just right for poolside fun. The pools and Jacuzzis of the hotel open daily, bright and early. Try a dip in the infinity pool or laps in the activity pool. All the pools of the hotel are open 12 hours a day.

Nighttime brings live music and theatre. Hotel guests can take a seat at one of two theatre showings, before or after dinner. Live entertainment options are available and the concierge will make sure guests know what’s in store during their stay. Live music is always on the menu, as is dancing and games of chance in the game room and billiard hall.

Book it now. Annie’s Revenge is an experience you won’t forget.