Cuban Sammy Stuffed Pork Loin & Mustard Vinaigrette

The aroma alone transports me back to Calle Ocho in Miami, where the air hums with the sounds of salsa and the irresistible scent of Cuban sandwiches being pressed to golden perfection. I remember wandering the streets as a young culinary student, marveling at the simple genius of those sandwiches – the crispy bread, the layers of savory pork, ham, and cheese, all brought together by a tangy mustard. That memory sparked a desire to capture all those flavors in a new, exciting way, and that’s how this stuffed pork loin was born.

Recipe Overview

• Prep Time: 30 minutes
• Cook Time: 25 minutes
• Total Time: 55 minutes
• Servings: 8
• Dietary Type: Not Gluten-Free

Ingredients

• 2 pork tenderloins, butterflied and pounded thin (3/4 – 1 lb each)
• Salt
• Pepper
• 3 tablespoons olive oil (to sauté the pork)

Marinade

• 1 cup olive oil
• 4 tablespoons lemon juice
• 4 tablespoons orange juice
• 2 teaspoons dried oregano
• 2 tablespoons minced garlic
• 2 teaspoons cumin
• 1⁄2 teaspoon red pepper flakes

Filling

• 3 cups fresh Cuban bread cubes
• 1 cup milk
• 2 tablespoons fresh parsley
• 2 teaspoons minced garlic
• 1 1⁄2 cups grated Swiss cheese
• 16 thin dill pickle slices
• 8 slices provolone cheese
• 16 slices of baked ham
• 1⁄2 teaspoon salt
• 1⁄4 teaspoon black pepper

Mustard Vinaigrette

• 3⁄4 cup olive oil
• 1⁄4 cup white wine vinegar
• 1 tablespoon shallot, finely chopped
• 1 1⁄2 tablespoons Dijon mustard
• 3 tablespoons heavy cream
• 2 teaspoons lemon juice (fresh)
• 1⁄4 teaspoon dried oregano
• 1 pinch sugar
• Salt
• Pepper

Equipment Needed

• Cutting board
• Meat mallet or rolling pin
• Ziploc bags or non-metal pan
• Large oven-proof pan (cast iron recommended)
• Butcher’s twine
• Blender

Instructions

1. Prepare the Pork Tenderloins: If your butcher hasn’t already done it, butterfly the pork tenderloins by slicing them horizontally, almost all the way through, and then opening them like a book. Place the butterflied tenderloins between sheets of plastic wrap and pound them to about 1/2 to 3/4 inch thickness. Be careful not to pound too close to the center to avoid tearing the two halves apart. You want them to remain connected at the fold.
2. Make the Marinade: In a measuring cup or small bowl, whisk together the olive oil, lemon juice, orange juice, dried oregano, minced garlic, cumin, and red pepper flakes.
3. Marinate the Pork: Place each pork tenderloin in a separate ziplock bag. Pour half of the marinade into each bag, seal, and shake to coat the pork thoroughly. Refrigerate for at least 4 hours, but no more than 8. If you prefer, you can use a large, non-metal pan instead of bags, ensuring the pork is fully submerged in the marinade.
4. Prepare the Cuban Bread Stuffing: Soak the diced Cuban bread in the milk for a few seconds, then squeeze out the excess milk thoroughly. In a bowl, combine the soaked bread with the grated Swiss cheese, fresh parsley, minced garlic, salt, and pepper. Mix well until everything is evenly distributed.
5. Assemble the Stuffed Pork Loin: Remove the pork tenderloins from the marinade and pat them dry with paper towels. Lay each tenderloin flat. Spread half of the bread and cheese stuffing evenly over the inside of each tenderloin, leaving a 1-inch border along one of the long edges.
6. Layer the Fillings: For each tenderloin, top the bread and cheese stuffing with 1/4 of the ham slices, then half of the dill pickle slices, followed by another 1/4 of the ham slices, and finally, half of the provolone cheese slices.
7. Roll and Secure: Carefully roll up each pork tenderloin, starting from the end with the stuffing. Secure each roll tightly with butcher’s twine at 1-inch intervals.
8. Sear the Pork Loin: In a large oven-proof pan (cast iron is ideal), heat the olive oil over medium-high heat. Season the rolled pork loins with salt and pepper. Sear the pork on all sides until golden brown.
9. Bake the Pork Loin: Transfer the pan to a preheated oven at 400°F (200°C). Bake for approximately 10-15 minutes, or until the internal temperature reaches 145°F (63°C) when checked with a meat thermometer inserted into the center of the stuffing. Remember that the pork will continue to cook slightly as it rests. I remove mine from the oven at 140-145 and let rest.
10. Make the Mustard Vinaigrette: While the pork is resting, prepare the mustard vinaigrette. Add everything except the olive oil to the blender and pulse a few times until well combined. Then slowly drizzle in the olive oil while blending on low speed until the dressing becomes creamy and emulsified.
11. Serve: Slice the stuffed pork loin into 1/2-inch thick medallions. Drizzle the mustard vinaigrette generously over the slices.

Expert Tips & Tricks

• Pounding the pork: Use even pressure when pounding the pork tenderloins to ensure a uniform thickness. This will help them cook evenly.
• Marinating time: While 4-8 hours is ideal, even a shorter marinating time (at least 30 minutes) will impart flavor to the pork.
• Cheese selection: If you can’t find pre-grated Swiss cheese, grating it fresh will provide a better flavor and melting quality.
• Bread soaking: Don’t over-soak the Cuban bread, or it will become mushy. A quick dunk and squeeze is all you need.
• Resting the meat: Allowing the pork loin to rest after cooking is crucial for retaining its juices and tenderness. Tent it loosely with foil for 10 minutes before slicing.
• Vinaigrette consistency: Adjust the amount of olive oil in the vinaigrette to achieve your desired consistency. More oil will result in a thicker, creamier dressing.

Serving & Storage Suggestions

Serve the sliced Cuban Sammy Stuffed Pork Loin hot, drizzled generously with the mustard vinaigrette. It pairs beautifully with yellow rice, black beans, roasted vegetables, and a fresh cucumber, green olive, onion and tomato relish served over a chopped salad, creating a vibrant and flavorful Cuban-inspired feast.

Leftovers can be stored in an airtight container in the refrigerator for up to 3 days. For best results, reheat the pork gently in a skillet or oven to prevent it from drying out. The mustard vinaigrette can also be stored in the refrigerator for up to 5 days. Do not leave the pork out at room temperature for more than 2 hours.

Nutritional Information

Nutrient	Amount per Serving	% Daily Value
Calories	730.2 kcal	N/A
Calories from Fat	624 kcal	85%
Total Fat	69.3 g	106%
Saturated Fat	17.7 g	88%
Cholesterol	49.9 mg	16%
Sodium	750.3 mg	31%
Total Carbohydrate	14 g	4%
Dietary Fiber	0.9 g	3%
Sugars	2.5 g	N/A
Protein	15.4 g	30%

Note: Nutritional information is an estimate and may vary depending on specific ingredients and portion sizes.

Variations & Substitutions

• Gluten-Free: Substitute the Cuban bread with a gluten-free bread alternative, making sure it has a similar dense texture to hold up well as stuffing.
• Cheese Variations: Experiment with other cheese combinations like Gruyere and Emmental for a slightly different flavor profile.
• Spicy Kick: Add a pinch of cayenne pepper or a few dashes of hot sauce to the marinade or vinaigrette for extra heat.
• Herb Variations: Try adding fresh cilantro or mint to the stuffing or vinaigrette for a refreshing twist.
• Vegetarian Option: Substitute the pork tenderloin with large portobello mushrooms marinated and stuffed with a vegetable mixture.

FAQs (Frequently Asked Questions)

Q: Can I make the stuffed pork loin ahead of time?
A: Yes, you can assemble the stuffed pork loin up to a day in advance. Wrap it tightly in plastic wrap and refrigerate it until you’re ready to sear and bake. Add a few extra minutes to the baking time if cooking from cold.

Q: Can I freeze the leftover pork loin?
A: Yes, you can freeze leftover slices of the pork loin. Wrap them individually in plastic wrap and then place them in a freezer-safe bag. Thaw overnight in the refrigerator before reheating.

Q: What’s the best way to check if the pork is cooked through?
A: The most reliable way is to use a meat thermometer. Insert it into the thickest part of the pork loin, making sure it doesn’t touch the stuffing. The internal temperature should reach 145°F (63°C).

Q: Can I grill the pork loin instead of baking it?
A: Absolutely! Sear the pork loin over medium-high heat and then move it to a cooler part of the grill to finish cooking. Keep the lid closed and monitor the internal temperature.

Q: Can I use a different type of bread for the stuffing?
A: While Cuban bread provides the most authentic flavor, you can substitute it with other dense, crusty breads like French bread or Italian bread. Just make sure to adjust the amount of milk you use for soaking to prevent the stuffing from becoming too wet.

Final Thoughts

I hope this recipe inspires you to bring a taste of Miami into your own kitchen! The combination of savory pork, salty ham, tangy pickles, and creamy mustard vinaigrette is a flavor explosion that’s sure to impress. Don’t be afraid to experiment with different ingredients and make it your own. And please, share your culinary creations and feedback with me – I’d love to hear how it turns out! Consider serving this with a crisp Mojito for the full Cuban experience. ¡Buen provecho!