When it’s summertime, dessert made on the grill is where it’s at! This Grilled Pineapple with Brown Sugar Glaze is the perfect way to top off an evening spent on the patio. Grilling pineapple brings out so much juicy flavor, and the brown sugar glaze (which includes Member’s Mark™ Ground Cinnamon) adds just a touch of additional sweetness. Top with ice cream or whipped cream to make it even more special!
How to Choose the Perfect Pineapple
What to look for
- Color: A ripe pineapple should have some golden-yellow color, especially toward the bottom. A fully green one can still ripen a bit, but a pineapple with more gold and less green is usually sweeter and more ready to eat.
- Smell: Sniff the bottom/base. It should smell sweet and fruity.
- No smell = probably underripe
- Fermented or boozy smell = overripe
- Feel: It should feel firm but not rock hard. A little give is okay, but it shouldn’t feel soft or mushy.
- Weight: Pick up a few and choose one that feels heavy for its size—that usually means it’s juicier.
- Leaves: The leaves should look green and fairly fresh, not dry and brown. If a center leaf pulls out very easily, it may be very ripe or past its prime.
- Skin condition: Avoid pineapples with:
- soft spots
- bruising
- mold
- wrinkled skin
- leaking juice
Best pineapple = this combo
If you want one that’s ready to eat soon, choose a pineapple that is:
- golden at the base
- sweet-smelling on the bottom
- heavy for its size
- firm with no soft spots
One helpful thing to know
Pineapples don’t get much sweeter after picking. They may soften a little at home, but they won’t dramatically ripen like a peach or banana. So it’s worth picking a good one at the store.
How to Cut a Pineapple into Rings
What you need
- Sharp chef’s knife
- Cutting board
- Small round cutter or paring knife (to remove the core)
Step-by-step
- Cut off the top and bottom
Slice off the leafy crown and the bottom so the pineapple can stand flat. - Trim off the skin
Stand the pineapple upright and slice downward, following the curve of the fruit to remove the peel.- Go around the pineapple until all the skin is off.
- If you see the little brown “eyes,” trim those away with a paring knife.
- Lay it on its side
Once peeled, place the pineapple on its side on the cutting board. - Slice into rounds
Cut crosswise into rings, about ½ inch to ¾ inch thick depending on how thick you want them. - Remove the tough center core
Each slice will have a hard core in the middle. Remove it by:- using a small round cookie cutter or biscuit cutter, or
- cutting around it carefully with a paring knife
For grilling pineapple rings
If you’re planning to grill them, cut them about ¾-1 inch thick so they hold together better on the grill.
Quick tip
If the pineapple is really juicy, pat the rings dry before grilling or caramelizing so they get better color.

Grilled Pineapple with Brown Sugar Glaze
Ingredients
- 1 cup Rum
- 2 tbsp Brown sugar
- 2 tsp Member's Mark™ Ground Cinnamon
- 2 tsp Pure vanilla extract
- 3 Pineapple slices sliced thick
- Lime zest for garnish
Instructions
- In a small bowl, make the sauce by whisking the rum, brown sugar, Member's Mark™ Ground Cinnamon, and vanilla extract.
- Add the pineapple slices and brown sugar sauce to a zip top back. Let marinate 30 minutes or overnight in the refrigerator.
- Grease a grill with butter. Preheat grill to medium heat. Remove the pineapple from the bag, and save the marinade. Grill pineapple for 3-5 minutes on one side.
- Once the pineapple has grill marks on one side, carefully flip and cook on another side until caramelized. Simmer and boil on low heat, stirring frequently.
- Cook until the sauce is thickened. Drizzle on top of the pineapple, and top with lime zest for garnish.