There’s something magical about smoky bacon, melty cheese, and tender pork all wrapped into one perfect bite.

The first time I tried these Cuban Pork Roll-Ups, they instantly reminded me of a Cuban sandwich—bold, juicy, slightly tangy, and packed with flavor in every bite.

Now they’ve become my go-to for weekend BBQs or game nights, and they never fail to impress.

If you love pork, bacon, and bold flavor, you’re in for a treat.

Why You’ll Love This Recipe

Bold Cuban sandwich flavor in every bite

Smoky bacon wrap locks in moisture

Melty Swiss cheese with tangy pickles = heaven

Easy to make, grill-friendly, and fun to eat

Perfect for parties or tailgates

What You’ll Need (Ingredient Highlights)

Thin sliced boneless pork chops – pounded thin, these serve as the “wrap”

Cubano Rub – brings zesty, garlicky seasoning to the pork

Bacon – smoky and crispy outer layer

Deli ham & Swiss cheese – the classic Cuban combo

Pickles & mustard – sharp, tangy contrast that makes it sing

Southbound Sauce – sweet and smoky glaze for the finish

Pro Tips Before You Start

Pound the pork chops evenly—too thick and they won’t roll well.

Use toothpicks to hold the roll together if needed while wrapping in bacon.

Don’t skip the resting time—it lets the juices redistribute for the juiciest result.

Preheat the grill and maintain consistent heat for even cooking.

How to Make Cuban Pork Roll-Ups

Step 1. Prep the Pork

Preheat your grill or smoker to 275°F.

Using a meat mallet, pound each pork chop to about 1/8” thickness.

Be gentle—you want them thin but intact.

Step 2. Build the Filling

Spread a thin layer of mustard on one side of each pork chop.

Add a slice of deli ham, Swiss cheese, and a few thin-cut pickles on top.

Step 3. Roll and Wrap

Roll the pork chop up tightly like a pinwheel.

Wrap each roll with 1–2 slices of bacon until completely covered.

Sprinkle generously with Cubano Rub for flavor.

Step 4. Grill to Perfection

Place the rolls on the grill.

Cook for 30–45 minutes or until internal temperature hits 135°F.

Step 5. Glaze and Finish

Brush each roll with Southbound Sauce and continue cooking for 10–15 minutes more, or until the internal temp reaches at least 145°F.

Step 6. Rest and Serve

Let the pork rolls rest for 5–10 minutes.

Serve warm with extra Southbound Sauce or mustard for dipping.

What to Serve It With

These pork roll-ups pair beautifully with:

Garlic butter corn on the cob

Grilled sweet potatoes

Creamy coleslaw or potato salad

Pickled red onions or jalapeños for a zingy bite

Variations & Substitutions

Try provolone or pepper jack instead of Swiss for a twist.

Use turkey or chicken breast if you want a leaner version.

No Cubano Rub? Mix garlic powder, smoked paprika, salt, and cumin.

Sub BBQ sauce for Southbound Sauce for a smokier finish.

Storage & Leftovers

Store leftovers in an airtight container in the fridge for up to 4 days.

Reheat in the oven at 300°F until warm.

You can freeze unglazed rolls for up to 2 months and cook them later.

FAQs

Can I make these ahead of time?
Yes! You can prep and roll them up to 24 hours in advance.

Keep refrigerated until ready to grill.

What’s a good substitute for Southbound Sauce?
Use your favorite BBQ sauce, or mix ketchup, brown sugar, and mustard for a quick glaze.

Can I cook these in the oven instead?
Absolutely. Bake at 375°F until they reach 145°F inside.

Broil the top for crispiness.

Do I have to pound the pork chops?
It’s highly recommended so you can roll them easily without tearing.

Can I make them spicy?
Yes! Add jalapeños inside or use spicy mustard for a kick.

What if I don’t have Cubano Rub?
You can mix garlic powder, cumin, oregano, and a pinch of cayenne for a quick DIY version.

Can I use turkey bacon?
Yes, but keep in mind it won’t crisp the same way as regular bacon.

Final Thoughts

These Cuban Pork Roll-Ups with Bacon and Cheese are the kind of dish that turns heads and disappears fast.

They’re a smoky, cheesy, pickle-packed party on your plate—and honestly, one of the most fun ways to level up pork chops.

Serve them up hot, slice into bite-sized rounds, and watch your guests devour them. You’ll want to make a double batch next time—trust me.

The Boat Shed Kitchen