Cut the first pineapple into chunks. To make fresh pineapple juice: place pineapple chunks in a high-speed blender, and turn on high for about 15-20 seconds. 1 cut pineapple makes approximately 3 cups of fresh pineapple juice if you blend all the pineapple chunks or you can keep some cut pineapple for snacks. The pineapple juice will be thick, and that is fine for this recipe. (set aside-this will go in the pineapple glaze)
Cut the second pineapple in half, set aside.
In a small saucepan, combine Kahlua, pineapple juice, brown sugar, honey, orange zest (zest the orange first then juice it), orange juice, Dijon mustard, cinnamon, grated ginger, and vanilla extract. Bring just to a boil, keep stirring with a whisk, reduce heat, and simmer for 3-5 minutes on low heat. Set aside off heat to cool.
Preheat oven to 275 degrees. Place spiral ham in a low roasting pan flat side down uncovered for a total of 2 hours for an 8 lb. ham (approximately 120 internal temperature). Depending on the size of your ham, bake it 12-15 minutes per pound.
After 1 hour, pull the ham out of the oven, place the 2 pineapple halves on each side of the ham and brush the ham and pineapples with the yummy glaze.
Place the ham back in the oven for 1 more hour until the glaze forms a nice crust. Reglaze the ham and pineapples every 15 minutes. You will have extra glaze let over.
Remove the tops from the pineapple halves and cut into smaller portions away from the pineapple skin. Carve and serve the ham and pineapple warm, enjoy!