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The Boat Shed Kitchen

Cuban Pork Roll-Ups

These Cuban Pork Roll-Ups are everything you love about a classic Cubano sandwich—savory pork, melty Swiss, zesty pickles, smoky bacon—rolled into one juicy, grilled bite. Smothered in tangy Southbound Sauce, they’re the ultimate handheld BBQ crowd-pleaser.
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Prep Time 20 minutes
Cook Time 50 minutes
Rest Time 10 minutes
Total Time 1 hour 20 minutes
Servings: 6
Calories: 420
Ingredients Method Notes

Ingredients
  

  • 2 pounds boneless pork chops thin sliced preferred
  • 6 oz sliced deli ham
  • 6 slices Swiss cheese
  • Thin cut pickle slices any variety
  • Yellow or deli mustard
  • 12 oz pack of regular or thin cut bacon
  • Cubano Rub to taste
  • Southbound Sauce 13.5 oz

Method
 

  1. Preheat grill or smoker to 275°F.
  2. Pound each pork chop to 1/8” thick using a meat mallet.
  3. Spread mustard on one side. Top with ham, cheese, and pickles.
  4. Roll each pork chop tightly and wrap with 1–2 slices of bacon.
  5. Season with Cubano Rub.
  6. Grill for 30–45 minutes until internal temp reaches 135°F.
  7. Brush with Southbound Sauce. Grill 10–15 more minutes until temp hits 145°F.
  8. See full steps with tips & photos → https://theboatshedcafe.com/cuban-pork-roll-ups/

Notes

  • Don’t skip the pounding step—it makes rolling easier and ensures tender bites.
  • Use thin-sliced bacon for quicker crisping.
  • Substitute your favorite BBQ sauce if Southbound Sauce isn’t available.