How I Celebrate More: Summertime Grilled Pineapple Dessert

Maggie Walters


Here's a decadent delight any time you're craving a sweet treat!

  • 1 large fresh pineapple, peeled, cored, and cut into long wedges
  • 1 cup dark brown sugar
  • Vanilla bean ice cream
  • 1 loaf Sara Lee pound cake (cut into thick slices)
  • 1 cup heavy whipping cream
  • 2 Tbsp granulated white sugar
  • 1 Tbsp spiced rum or vanilla extract  
  • Mint for garnish

Whisk heavy whipping cream in a metal bowl until stiff peaks form, slowly adding in the sugar. Once desired texture is reached, fold in the rum or vanilla extract. Place in fridge to keep cool.

In a large mixing bowl, toss pineapple wedges and brown sugar until fully coated. Let sit for about 15 minutes, stirring every so often.

Put pineapple wedges on a preheated grill, reserving brown sugar pineapple juice left behind in the mixing bowl. Grill the pineapple on each side for about 3 minutes or until caramelized and grill marks are visible. Remove from grill and let cool.


Place thick pound cake slices on the grill, cooking each side until toasty and warm, about 2 minutes. Remove from grill.

For plating, gather grilled pineapple wedges, grilled pound cake, whipped cream, ice cream, and brown sugar syrup. Place pound cake on plate first, lay a pineapple wedge askew to the cake, scoop a spoonful of ice cream in between the two, add a dollop of whipped cream, and brown sugar syrup to desired amount. Garnish with mint. 

Suggested beverage pairings:

Kermit Lynch Sori Gramela Moscato D’Asti

– for a sweet and spritzy dessert wine

Kirk and Sweeney 12year old rum

– served over a large ice cube

Pro Tip:

When picking out a pineapple, check the bottoms of the fruit! The riper in color and more aromatic ones are the best


I head straight for the Moscato section at Colonial! A sweet treat calls for sweet wine. Dessert just makes dry wine taste sour (oh no!). I don’t choose just any ole Moscato though. I go for a true Moscato d’Asti from Asti, Italy, imported by my favorite wine importer, Kermit Lynch. His stuff is top of the line!!


Now to get my hands dirty, or should I say sticky. I cut the thick ends of the pineapple away and then stand the now flat-bottomed fruit upright on a cutting board so I can cut away the thick peel. After the peel and eyes are completely cut off I cut the fruit away from the core creating big juicy wedges. I heat my grill up to high heat, then reduce to medium and start my favorite part, the grilling! The grilled pineapple smells SO good with all of the brown sugar heating up and creating a caramel coating, YUM! I set the pineapple aside and do the same with the pound cake; slice and grill!

Now that I have all aspects of my dish made, I set them all out on the counter to plate! I have my grilled pineapple, grill pound cake, homemade whipped cream, brown sugar syrup leftover from marinating the pineapples, and last but not least, vanilla bean ice cream. Any brand will do, I went with my favorite, Haagen-Dazs!


Here’s the final product! It doesn’t have to be perfect, it tastes good no matter how messy assembly gets! Here is my wine of choice, the Sori Gramella Moscato d’Asti from Kermit Lynch! If you have anyone at your table who loves spirits this also pairs really well with rum!