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4.8 from 51 votes

Italian Stuffed Flank Steak

Any steak lover will give this Italian Stuffed Flank Steak a big thumbs up! The steak is marinated to tenderize and lock in the amazing flavors, and then it's rolled in an unbelievably delicious walnut pesto filling with prosciutto, roasted bell peppers and provolone cheese.

Prep Time
20 mins
Cook Time
20 mins
Marinating Time
2 hrs
Total Time
3 hrs 5 mins
Servings: 6
Calories: 564 kcal
Course: Main Course , Dinner
Cuisine: Italian , American

Ingredients

Marinade
  • ¼ cup olive oil
  • ¼ cup red wine vinegar
  • 3 cloves garlic minced
  • ½ teaspoon salt
  • ½ teaspoon pepper freshly ground
  • ¼ cup fresh parsley chopped
Walnut Pesto
  • ½ cup walnuts
  • 2 cloves garlic smashed
  • ½ cup Parmesan Cheese grated
  • 2 ounces fresh basil
  • ¼ cup olive oil
  • ¼ teaspoon salt
  • ¼ teaspoon pepper
Flank Steak
  • 1½ pounds flank steak
  • 6 lices prosciutto
  • 2 roasted red peppers
  • 6 lices Provolone cheese
  • salt and pepper to taste
  • 2 tablespoons olive oil

Instructions

    Cup of Yum
  1. Prep the steak. Using a boning knife, slice the meat horizontally on the long side of the steak, but do not cut all the way through, leave about ½ inch uncut. You want the steak to open like a book. Make sure the top half is the same thickness as the bottom half. Open up the steak so that it's flat. Use a meat mallet to pound down the steak to a uniform thickness about ½ inch in thickness or thinner.
  2. Make the marinade and marinate the steak. Add all the marinade ingredients to a large bowl and whisk to combine. Add the butterflied steak to the bowl and toss it around in the marinade to coat it all around. Cover the bowl with plastic wrap and refrigerated for 2 hours.
  3. Prep the oven. Preheat the oven to 350°F.
  4. Make the walnut pesto. In a food processor add all the pesto ingredients and pulse a few times, don’t over process as you don’t want a smooth consistency. Taste for salt and pepper and add more if needed.
  5. Assemble the steak. Remove the steak from the marinade; reserve marinade. Place the steak flat on a cutting board. Spread the pesto evenly over the steak, leaving about ½ inch free on all sides of the meat. Layer the steak with prosciutto slices, followed by roasted peppers, then provolone cheese slices. Sprinkle with salt and pepper. Roll up the steak jellyroll style. The grain of the steak should run on the length of the roll. Tie the roll with kitchen twine or string, every 2 inches. Brush with remaining marinade.
  6. Sear the steak. Add the olive oil to an oven safe skillet and heat over medium-high heat. Add the steak roll and sear quickly on all sides until brown.
  7. Roast the roll. Transfer the skillet to the preheated oven and roast for 30 to 40 minutes or until the interior of the meat registers at 130°F when tested with an instant read meat thermometer.
  8. Rest the meat and slice. Remove the skillet from the oven and let the steak rest for 10 minutes. Remove the string from the roll and cut into slices.

Notes

  • Make sure your knife is sharp to get a good clean even cut in your steak.
  • When you flatten the steak, don't make it too thin, it may rip. Only pound it if it's not thin enough, mine was already about ½ inch in thickness so there was no need to pound it.
  • Use your favorite cheese, other cheeses that would be great would be Swiss cheese or Havarti.
  • Don't skip the searing part for that delicious brown crust. A cast iron skillet is best for a good sear.
  • Best and safest way to determine when your roll is cooked is to use a meat thermometer.

Nutrition Information

Serving 1serving Calories 564kcal (28%) Carbohydrates 4g (1%) Protein 35g (70%) Fat 45g (69%) Saturated Fat 12g (60%) Polyunsaturated Fat 8g Monounsaturated Fat 23g Trans Fat 1g Cholesterol 92mg (31%) Sodium 876mg (37%) Potassium 557mg (16%) Fiber 1g (4%) Sugar 1g (2%) Vitamin A 1012IU (20%) Vitamin C 12mg (13%) Calcium 308mg (31%) Iron 3mg (17%)

Nutrition Facts

Serving: 6Serving

Amount Per Serving

Calories 564

% Daily Value*

Serving 1serving
Calories 564kcal 28%
Carbohydrates 4g 1%
Protein 35g 70%
Fat 45g 69%
Saturated Fat 12g 60%
Polyunsaturated Fat 8g 47%
Monounsaturated Fat 23g 115%
Trans Fat 1g 50%
Cholesterol 92mg 31%
Sodium 876mg 37%
Potassium 557mg 12%
Fiber 1g 4%
Sugar 1g 2%
Vitamin A 1012IU 20%
Vitamin C 12mg 13%
Calcium 308mg 31%
Iron 3mg 17%

* Percent Daily Values are based on a 2,000 calorie diet.