Trim all visible fat from the ham. Place the ham in a large pot or Dutch oven. With a knife, make 2 diagonal slashes lengthwise and 3 diagonal slashes cross-wise on top of the ham. Arrange 12 cloves around the incisions. Cover the ham with the pineapple slices.
Arrange 5 cherries between the pineapple slices. Cover and cook on medium-high heat for 1/2 hour on one side. Remove the pineapple slices and cherries from the top; set aside.
Using two serving forks, turn the ham to brown the other side. Cook an additional 1/2 hour.
In a saucepan, combine the pineapple juice, wine if desired, and maple syrup. Add the remaining 3 cloves and 3 cherries to the liquid. Place the reserved pineapples in the liquid. Cook for about 15 minutes or until the liquid becomes syrupy and the pineapples are caramelized.
Remove the ham from the pot-using the same method with the forks and place on a platter with the incisions (diagonal slashes) facing up. Keep warm.