Quick Recipe Version (TL;DR)

Yield: 10–12 servings
Prep Time: 25 minutes
Cook Time: 2 hours 15 minutes
Total Time: 2 hours 40 minutes (including resting)

Quick Ingredients

1 fully cooked bone-in ham, 8–9 lb (spiral-sliced or whole)
24–36 whole cloves
1 cup packed dark brown sugar
1/3 cup honey
1/3 cup bourbon
2 tbsp Dijon mustard
2 tbsp whole-grain mustard
2 tbsp unsalted butter (plus 2 tbsp more for pineapple)
2 tbsp apple cider vinegar or orange juice
1/2 tsp ground cinnamon and ground ginger (total)
1 fresh pineapple (or 1 can pineapple rings) + 1/4 cup brown sugar
1–1 1/2 cups water for roasting pan
Optional: maraschino cherries for garnish

Do This

1. Preheat oven to 300°F (150°C). Place ham cut side down on a rack in a roasting pan; pour 1–1 1/2 cups water into the pan. Score the fat in a diamond pattern and stud with cloves. Cover tightly with foil.
2. Bake for 60 minutes while you make the glaze: simmer brown sugar, honey, bourbon, mustards, butter, vinegar/juice, and spices in a saucepan for 5–7 minutes until syrupy.
3. After 60 minutes, uncover ham and brush with about one-third of the glaze. Re-cover loosely and bake 30–40 minutes more, until warmed through (about 110–120°F / 43–49°C in the center).
4. While ham bakes, caramelize pineapple rings in a skillet with 2 tbsp butter and 1/4 cup brown sugar, 3–4 minutes per side, until deep golden and glossy. Set aside.
5. Increase oven to 400°F (200°C). Uncover ham, brush generously with more glaze, and bake 15–20 minutes, basting every 5 minutes, until mahogany brown and internal temp reaches 135–140°F (57–60°C).
6. For extra caramelization, spoon remaining glaze over ham, arrange pineapple rings (and cherries if using) on top, and roast or broil 2–3 minutes, watching closely.
7. Rest ham 10–15 minutes before slicing. Serve with caramelized pineapple and pan juices spooned over the top.

Why You’ll Love This Recipe

Classic holiday ham flavor with a deep, glossy brown-sugar and honey-bourbon glaze that tastes like it came from a fancy country inn.
Perfect balance of sweet, tangy, and gently boozy, with a hint of spice from Dijon mustard and warm baking spices.
Caramelized pineapple rings and clove-studded ham give you a gorgeous, show-stopping centerpiece with very little fuss.
Use either spiral-sliced or whole ham, and the recipe scales easily for different crowd sizes.

Grocery List

Produce: 1 fresh pineapple (or canned rings), 1 orange (if using juice), optional fresh herbs (rosemary or thyme) for garnish
Dairy: Unsalted butter
Pantry: Fully cooked bone-in ham, dark brown sugar, honey, bourbon, Dijon mustard, whole-grain mustard, apple cider vinegar, ground cinnamon, ground ginger, ground black pepper, whole cloves, optional maraschino cherries, optional cayenne pepper, kosher salt (for seasoning pineapple if desired)

Full Ingredients

For the Ham

1 fully cooked bone-in ham, 8–9 lb (3.6–4.1 kg), spiral-sliced or whole
24–36 whole cloves (enough to stud the ham in a loose pattern)
1–1 1/2 cups (240–360 ml) water, for the roasting pan

For the Brown-Sugar Honey-Bourbon Glaze

1 cup (200 g) packed dark brown sugar
1/3 cup (80 ml) honey
1/3 cup (80 ml) bourbon
2 tbsp Dijon mustard
2 tbsp whole-grain mustard
2 tbsp unsalted butter
2 tbsp apple cider vinegar or freshly squeezed orange juice
1/4 tsp ground cinnamon
1/4 tsp ground ginger
1/4 tsp freshly ground black pepper
Pinch of cayenne pepper (optional, for gentle heat)

For the Caramelized Pineapple

1 fresh pineapple, peeled, cored, and sliced into 1/2-inch (1.25 cm) thick rings

or 1 can (20 oz / 567 g) pineapple rings in juice, well drained
2 tbsp unsalted butter
1/4 cup (50 g) packed brown sugar
Pinch of kosher salt (optional, to balance sweetness)
Optional: 10–12 maraschino cherries (for the centers of the pineapple rings, classic presentation)

For Serving and Garnish (Optional)

Fresh herbs such as rosemary or thyme sprigs
Extra bourbon or orange juice to thin leftover glaze if needed

Step-by-Step Instructions

Step 1: Preheat the oven and prepare the roasting pan

Position a rack in the lower third of your oven and preheat to 300°F (150°C).

Fit a roasting rack inside a large roasting pan. Pour 1–1 1/2 cups water into the bottom of the pan (this keeps the ham moist and prevents drippings from burning). Place the ham cut side down on the rack. If you do not have a rack, you can rest the ham on thickly sliced onions or simply directly in the pan.

Pat the ham dry with paper towels so the glaze will cling better later.

Step 2: Score and clove-stud the ham

Using a sharp knife, lightly score the fat and skin of the ham in a diamond pattern. Make cuts about 1/4 inch (6 mm) deep and 1 inch (2.5 cm) apart. Do not cut too deeply into the meat; you are mainly cutting through the outer fat cap.

At some of the diamond intersections, press a whole clove into the ham. You can stud every intersection for a very traditional look or just a scattered pattern for a milder clove flavor. Aim for about 24–36 cloves total.

Tent the entire pan tightly with aluminum foil, crimping the edges around the pan so steam is trapped inside.

Step 3: Start baking the ham slowly

Transfer the foil-covered ham to the preheated oven. Bake for 60 minutes while you prepare the glaze. This gentle start allows the ham to warm through without drying out.

Remember, the ham is fully cooked already; you are reheating it and infusing it with flavor. The final internal temperature you are aiming for later is 135–140°F (57–60°C).

Step 4: Make the brown-sugar honey-bourbon glaze

While the ham bakes, make the glaze. In a medium saucepan, combine:

1 cup dark brown sugar
1/3 cup honey
1/3 cup bourbon
2 tbsp Dijon mustard
2 tbsp whole-grain mustard
2 tbsp unsalted butter
2 tbsp apple cider vinegar or orange juice
1/4 tsp ground cinnamon
1/4 tsp ground ginger
1/4 tsp black pepper
Pinch of cayenne (optional)

Set the pan over medium heat and bring the mixture to a simmer, stirring often. Reduce heat to medium-low and simmer for 5–7 minutes, or until the glaze thickens slightly and becomes syrupy and glossy. It should coat the back of a spoon.

Remove the saucepan from the heat and let the glaze cool slightly. It will thicken a bit more as it stands. Reserve about 1/4 cup for a final glossy drizzle just before serving, if desired.

Step 5: Glaze the ham and continue baking

After the ham has baked for 60 minutes, carefully remove it from the oven and peel back the foil. Increase the oven temperature remains at 300°F (150°C) for now.

Brush the ham generously with about one-third of the warm glaze, making sure to get into the scored lines and between the slices if using a spiral ham. Recover the ham loosely with foil (do not seal tightly this time) and return it to the oven.

Bake for another 30–40 minutes, basting once halfway through with some of the pan juices. At this point, the ham should be nicely warm in the center, around 110–120°F (43–49°C).

Step 6: Caramelize the pineapple rings

While the ham finishes its gentle bake, prepare the pineapple. If using fresh pineapple, peel it, remove the core, and slice into 1/2-inch (1.25 cm) thick rings. If using canned pineapple, drain the rings very well.

In a large skillet over medium heat, melt 2 tbsp butter. Stir in 1/4 cup brown sugar and an optional pinch of salt until it forms a thin caramel sauce.

Add pineapple rings in a single layer (work in batches if needed). Cook for 3–4 minutes per side, or until the edges are deeply golden and the centers are glossy and lightly translucent. They should look caramelized but not burned.

Transfer the caramelized pineapple to a plate to cool slightly. They will firm up a bit as the caramel sets. Reserve any extra caramel in the pan for drizzling over the ham later if you like.

Step 7: Finish the ham at high heat with more glaze

When the ham has finished its slow bake, remove the foil entirely. Increase the oven temperature to 400°F (200°C).

Brush the ham generously with about half of the remaining glaze. Return the ham to the oven, uncovered, and bake for 15–20 minutes, basting every 5 minutes with more glaze and some of the pan juices. The surface should turn a deep mahogany brown and become shiny and slightly sticky.

During this time, the internal temperature should reach 135–140°F (57–60°C). If it is not quite there, leave the ham in a little longer, loosely covered with foil to prevent burning while it finishes warming.

In the last 2–3 minutes, you can arrange the caramelized pineapple rings over the top of the ham and around the edges. For a classic look, tuck a maraschino cherry into the center of each ring. Spoon a bit of glaze over the pineapple and place the ham back in the oven (or briefly under the broiler) just until everything is bubbling and lightly caramelized. Watch very closely to avoid scorching the sugar.

Step 8: Rest, slice, and serve

Remove the ham from the oven and transfer it carefully to a cutting board or serving platter. Tent loosely with foil and let it rest for 10–15 minutes. This helps the juices redistribute so the meat stays moist when sliced.

If your ham is spiral-sliced, simply cut along the bone to release the pre-cut slices. For a whole ham, slice thinly across the grain. Arrange slices on a warm serving platter and nestle the caramelized pineapple rings around and over the ham.

Thin the reserved glaze with a splash of hot water, bourbon, or orange juice if it has thickened too much, then drizzle some over the sliced ham. Serve any remaining glaze and pan juices in a small pitcher or bowl on the side.

Pro Tips

Keep it moist: The water in the bottom of the roasting pan plus tightly tented foil at the start are key to keeping the ham juicy. Do not skip them.
Do not overcook: Since the ham is already fully cooked, your goal is to reheat to 135–140°F (57–60°C) and develop flavor. Overcooking will dry it out.
Adjust sweetness to taste: For a less sweet glaze, reduce the brown sugar by 2–3 tbsp or add an extra splash of vinegar or orange juice for brightness.
Use the right pan: A sturdy roasting pan with high sides helps contain splatters from the sugary glaze and makes cleanup easier.
Slice against the grain: If working with a whole (non-spiral) ham, always slice across the grain of the meat for the most tender texture.

Variations

Maple-bourbon ham: Swap half or all of the honey for pure maple syrup. The maple adds deep, woodsy sweetness that pairs beautifully with bourbon.
Orange-clove ham: Use orange juice instead of vinegar, add 1–2 tsp orange zest to the glaze, and increase the cloves slightly for a citrusy, spiced twist.
No-alcohol version: Replace the bourbon with apple cider or additional orange juice. You will still get great caramelization and flavor without the alcohol.

Storage & Make-Ahead

Make-ahead: You can score and clove-stud the ham, mix the glaze, and prep the pineapple up to 1 day in advance. Store the ham covered in the fridge, the glaze in a sealed jar, and the pineapple rings in an airtight container. Let the ham sit at room temperature for 30–45 minutes before baking.

Leftovers: Store leftover ham slices and pineapple in airtight containers in the refrigerator for up to 4 days. The ham can also be frozen (tightly wrapped) for up to 2 months. Thaw overnight in the refrigerator before reheating.

Reheating: Reheat ham slices, covered, in a 300°F (150°C) oven with a splash of water or broth until warmed through, about 15–20 minutes. Alternatively, warm individual portions gently in a covered skillet with a spoonful of water or leftover glaze.

Nutrition (per serving)

Approximate values for one serving (about 4 oz / 115 g cooked ham plus some glaze and pineapple): 400–430 calories, 24–26 g protein, 17–19 g fat, 28–32 g carbohydrates, 24–28 g sugars, 1,200–1,500 mg sodium. Actual values will vary based on the exact ham, amount of glaze consumed, and portion size.

Festive Brown Sugar Bourbon Ham With Caramelized Pineapple