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Home / Main Dishes / Beef

Italian Stuffed Flank Steak

4.60
/5
35 minutes minutes
155 Comments
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By: The Chunky Chefpublished: 05/20/2018

This post may contain affiliate links. Please read my disclosure policy.

Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese… flavorful steak pinwheels that are every bit tasty as they are fancy-looking!

If you’re ready for a gourmet steak meal with a twist, this is the flank steak recipe for you!

Impress anyone with this easy flank steak that's rolled with garlic, herbs, prosciutto ham and provolone cheese

 

Looking for a fancy schmancy meal to serve up for a dinner party?  Or maybe your boss is coming over for dinner?  Or you know what, maybe you just want to treat yourself to a fancy looking meal… you deserve it! 🙂  Look no further than this stuffed flank steak recipe.  It’s a great twist on a regular grilled steak.

It may look incredibly complicated, but trust me, it’s not!  It uses flank steak, which I’ve used before in my garlic beef stir fry, and my slow cooker Mongolian beef… I love it for it’s versitality and relatively good price tag.

HOW TO MAKE STUFFED FLANK STEAK

This is one of those total fake-out meals, because it looks super impressive… yet is actually fairly easy to make!

You’ll make this steak go a little further by butterflying it open and pounding it thin.  While the steak is resting on your cutting board, take your knife and slice it horizontally across the steak, so you end up with 2 halves of the steak.

Butterflied flank steak on cutting board

Now you’re going to need some wax paper and either a small heavy skillet, rolling pin, or a meat tenderizer tool.  Place wax paper on top of your cutting board, put your steak on top of that, then add another layer of wax paper on top of the steak.  Get to work pounding it pretty thin.  You can pound it as thin as you’d like, but keep in mind that you’ll need to roll it up, so don’t make it so thin that there are holes.

Combine your minced garlic, shallots, parsley, sage, basil and olive oil in a small bowl.  After the steak is thin, spread an even layer of the garlic mixture over the surface.

Butterflied flank steak with garlic herb mixture

Then lay the prosciutto slices on top of that, followed by the slices of provolone cheese.

Butterflied flank steak with layers of prosciutto ham

Now comes the fun part!  Start with the end of the steak closest to you and roll it up towards the top into a tight log, and place the seam side down on the cutting board.

Italian flank steak rolled up in log

Grab some kitchen twine and tie up the steak in one to one and a half inch intervals all down the log.  Take your knife (make sure it’s sharp!) and slice in between the twine so the steaks are little pinwheels.  Take a toothpick and skewer the pinwheel so it’s secure.

Steak medallions rolled up on cutting board

 

In the summer I send these outside with my husband to be grilled to perfection, but when it’s raining or off-season, I sear them in my cast iron pan, and slide the pan into the oven to finish cooking.  It works really well!!

Stuffed flank steak pinwheels in cast iron pan

HOW LONG DO YOU COOK STUFFED FLANK STEAK

You may have seen a few stuffed flank steak recipes where the entire “log” is cooked, then it’s sliced right before eating.  That type of recipe will cook longer, about 30-40 minutes in a 350 degree oven.  Since this recipe calls for slicing the meat into pinwheels BEFORE cooking, the cook time is shorter, about 13-15 minutes, or until your steak reaches your desired temperature.

HOW DO I KNOW IF MY STEAK IS COOKED TO THE DESIRED TEMPERATURE

It’s hard to judge this type of steak recipe by feel as it cooks, so a meat thermometer will really be your best bet.  They’re pretty inexpensive these days, and are crucial to making sure your steak is perfectly cooked.  Since all meat continues to cook after you remove it from the oven or grill, you’ll want to pull your stuffed flank steak at the following temperatures, and let it rest 5-10 minutes (tented with aluminum foil), which will bring it up to the perfect temperature.

Rare: 120 F degrees (will come up to 125 F degrees)

Medium Rare: 130 F degrees (will come up to 135 F degrees)

Medium: 140 F degrees (will come up to 145 F degrees)

Medium Well: 145 F degrees (will come up to 150 F degrees)

Well Done: 155 F degrees (will come up to 160 F degrees)

Cooked Italian stuffed flank steak on white plate with parsley

I’m telling you… these wow’ed my family!  Even my kids scarfed these down… for real!

These flank steak pinwheels don’t really need any sauce, they’re flavorful enough as is… but I felt like being a little decadent and drizzled some balsamic glaze over the top.

But if you’d rather go for something else, your favorite steak sauce could also be used.

Italian stuffed flank steak medallions on plate with drizzle of balsamic glaze

IS THIS FLANK STEAK RECIPE HEALTHY

I would say traditionally, no.  Even though flank steak is a lean cut of meat, it’s still red meat, and it’s stuffed with cheese and salty ham.  However, if you’re following a low-carb or keto way of eating, it’s a fabulous healthy recipe!  At only 2 grams of carbs per serving (without the optional balsamic glaze), you can enjoy without the guilt.  It’s also a great source of protein and fat, as well as giving you over 22% of your daily iron!

Recipe originally posted in 2015, and has been updated in 2018.

HELPFUL TOOLS

  • Cast Iron Skillet – crucial for the BEST sear!
  • Meat Thermometer – I have this thermometer and love it, but I love my new tool too…
  • In-Oven Meat Thermometer – the probe stays in the meat while it’s in the oven, so you don’t need to keep opening the oven or grill to check the temperature over and over!
  • Meat Mallet – my all-time favorite tool for pounding steak or chicken… I love the wide surface!

Want to try this Stuffed Flank Steak?

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Did you make this? Be sure to leave a review below and tag me @the_chunky_chef on Facebook and Instagram!

Impress anyone with this easy flank steak that's rolled with garlic, herbs, prosciutto ham and provolone cheese.  Perfect on the stove/oven, or on the grill, these are the ultimate Italian steak pinwheels! #steak #flanksteak #stuffed #pinwheels #grilled #baked #Italian #steakpinwheels #steakmedallions

Italian Stuffed Flank Steak

4.60 from 44 votes
Author: The Chunky Chef
Prep Time: 20 minutes minutes
Cook Time: 15 minutes minutes
Total Time: 35 minutes minutes
Calories: 599
Servings: 4 servings
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Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking!

Ingredients

  • 3 - 4 cloves garlic minced or pressed through garlic press
  • 1 small shallot minced
  • 2 Tbsp fresh parsley finely minced
  • 1 tsp sage leaves finely minced
  • 1 tsp basil minced
  • 2 Tbsp olive oil
  • 2 - 2 1/2 pounds flank steak
  • 4 ounces thinly sliced prosciutto
  • 4 ounces thinly sliced provolone cheese
  • toothpicks soaked water for 10 minutes
  • Salt and pepper to taste

Instructions

  • Combine garlic, shallot, parsley, basil, sage, and olive oil in small bowl.
  • Slicing horizontally across the steak, butterfly and pound flank steak into 2 thin rectangles. Position steak so that the grain runs parallel to the edge of the counter, spread herb mixture evenly over surface of steak.
  • Lay prosciutto evenly over steak, leaving 1-inch border along top edge.
  • Cover prosciutto with even layer of cheese, leaving 1-inch border along top edge.
  • Starting from bottom edge and rolling up away from you, towards the top, roll steak into tight log and place on cutting board seam-side down.
  • Starting in the middle of the steak roll, tie a piece of kitchen twine to secure the steak. Working outward from the center, place more ties of kitchen twine, in one inch intervals, until the whole steak roll is tied up.
  • Using a sharp knife, slice roll between pieces of twine into 1-inch-thick pinwheels. Season pinwheels lightly with salt and black pepper.
  • Skewer each pinwheel with a toothpick.
  • Preheat oven to 350.
  • Heat a cast iron skillet over medium high heat. Place pinwheels in pan and brown for 3 minutes or so. Flip over and brown on the other side for 2 minutes.
  • Slide skillet into preheated oven and cook for about 8-10 minutes or until steak reaches desired doneness.
  • Remove from oven, tent with aluminum foil and let rest for 5 minutes.
  • Remove twine and toothpicks and enjoy!

Want to save this recipe for later? Click the heart in the bottom right corner to save to your own recipe box!

Chef Tips

Recipe adapted from Kathrynannew

Nutrition Disclaimer

The Chunky Chef is not a dietician or nutritionist, and any nutritional information shared is an estimate. If calorie count and other nutritional values are important to you, we recommend running the ingredients through whichever online nutritional calculator you prefer. Calories can vary quite a bit depending on which brands were used.

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Calories: 599 | Carbohydrates: 2g | Protein: 59g | Fat: 37g | Saturated Fat: 14g | Cholesterol: 174mg | Sodium: 558mg | Potassium: 909mg | Sugar: 0g | Fiber: 0g | Vitamin A: 8.2% | Vitamin C: 4.5% | Calcium: 27.2% | Iron: 22.2%

I’m not a nutritionist, and nutritional values here on my recipes should be used for general information purposes only.  This information is not a substitute for medical advice or treatment for specific medical conditions. You should seek prompt medical care for any specific health issues and consult your physician before starting a new diet and fitness regimen.

 

 

 

Impress anyone with this easy flank steak that's rolled with garlic, herbs, prosciutto ham and provolone cheese.  Perfect on the stove/oven, or on the grill, these are the ultimate Italian steak pinwheels! #steak #flanksteak #stuffed #pinwheels #grilled #baked #Italian #steakpinwheels #steakmedallions

Impress anyone with this easy flank steak that's rolled with garlic, herbs, prosciutto ham and provolone cheese.  Perfect on the stove/oven, or on the grill, these are the ultimate Italian steak pinwheels! #steak #flanksteak #stuffed #pinwheels #grilled #baked #Italian #steakpinwheels #steakmedallions

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Meet The Chunky Chef

Hey there! I'm Amanda. Wife, mother, photography nerd, and bacon lover! I believe that delicious meals should be easy to make. Now that you’re here, stay a bit, browse a few recipes, and let’s get cookin’!

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4.60 from 44 votes (13 ratings without comment)

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Recipe Rating




  1. Sarah says

    Posted on 7/22 at 2:03 pm

    Very well written recipe! I only had half the amount of steak, so I cut most measurements in half. I didn’t cut the herb measurements however, and it worked really well for me. We had about 4 pieces per person with a side salad. I forgot to pound my steak, but the meat wasn’t tough at all – it was perfectly juicy and chewy. That cast iron skillet works wonders!!

    Reply
  2. Wesley says

    Posted on 4/2 at 12:14 pm

    When I put these into the oven after searing on both sides, how should they be positioned? Cut side up or down or standing vertically on the steak?

    Reply
    • The Chunky Chef says

      Posted on 4/3 at 9:25 am

      I prefer cut side up, but you can do either one 🙂

      Reply
  3. Kim says

    Posted on 3/15 at 8:45 pm

    Soooooooo Good. I followed the recipe exactly and it was delicious, so much flavor. Definitely keeping this one on my list to make again.

    Reply
  4. Jim says

    Posted on 1/29 at 4:10 pm

    I didn’t see a recipe for the balsamic glaze is it just a reduction or is there more to it

    Reply
    • The Chunky Chef says

      Posted on 1/29 at 8:15 pm

      You can make your own by reducing balsamic vinegar until it’s thick and syrupy, or you can use store-bought glaze (which is what I did).

      Reply
  5. Mariah says

    Posted on 11/11 at 2:38 pm

    Hi! I was just wondering if you place the pinwheels cut side down or brown all of the steak around the pinwheel? Thanks!

    Reply
    • The Chunky Chef says

      Posted on 11/11 at 3:27 pm

      I normally brown the pinwheels cut side down (on both sides) because I love the caramelized cheese, but you can do either one, or even both… whichever way you’d like 🙂

      Reply
      • Mariah says

        Posted on 11/11 at 4:01 pm

        Thank you! I’m almost through prep and am SO excited for dinner tonight!

        Reply
  6. David M Bentley says

    Posted on 9/18 at 5:36 pm

    Fantastic ! Recipe if you love flavors that complement your meat this is the one your going to love,prep is minimal.And what you receive is fantastic,a must do. Thanks.

    Reply
    • Starlene says

      Posted on 1/15 at 5:48 am

      I don’t have a cast iron pan. Can i sear the pinwheels in a regular pan and transfer to a cookie sheet for in the oven?

      Reply
      • The Chunky Chef says

        Posted on 1/15 at 10:21 am

        Yes 🙂

        Reply
  7. Steve waite says

    Posted on 6/26 at 2:27 am

    Hi This looks fantastic.
    I’m going to try this on Saturday. I was just wondering how many adults this recipe would serve?
    I’d like to get about 7 servings. I’d appreciate any help or advice. Thanks
    Steve

    Reply
    • The Chunky Chef says

      Posted on 6/26 at 8:09 am

      Hi Steve 🙂 It depends on how hungry your guests are, but I would say for 7 servings, as a main dish, you’d want to double the recipe.

      Reply
      • Steven Waite says

        Posted on 6/26 at 12:47 pm

        Hi, Thanks for getting back to me so soon. Really looking forward to trying this and impressing the wife 🙂 I’ll let you know how it goes. Thanks again

        Reply
  8. Stacie says

    Posted on 6/14 at 9:42 am

    This looks great. I think it will be Father’s Day dinner at our house. Can you post the grilling directions because in our family on Father’s Day, Dad grills out! 😎

    Reply
    • The Chunky Chef says

      Posted on 6/14 at 7:57 pm

      Hi Stacie 🙂 Here’s what another reader has done… Grill pinwheels directly over hot side of grill until well browned, 3 to 6 minutes. Using tongs, flip pinwheels; grill until second side is well browned, 3 to 5 minutes longer. Transfer pinwheels to cooler side of grill, cover, and continue to cook 1 to 4 minutes (slightly thinner pinwheels may not need time on cooler side of grill). Transfer pinwheels to large plate, tent loosely with foil, and let rest 5 minutes. Remove and discard skewers and twine and serve immediately.

      Reply
  9. Jack Smith | BBQRecipez.com says

    Posted on 6/8 at 9:33 pm

    This is another genius recipe! The flavors, the aroma, the colors, well just everything about this dish is perfection.

    Reply
  10. Rick says

    Posted on 5/28 at 6:57 pm

    We tried this recipe tonight for the first time and loved it! Followed the recipe pretty much as provided, except added a just a dash of Italian Seasoning just prior to placing on the grill. Using the gill may have caused a loss on some of the cheese but not enough to ruin the dish.. We also went with the balsamic glaze which definitely was a plus. We will put this one in our rotation!

    Reply
  11. Amy @ Little Dairy on the Prairie says

    Posted on 5/22 at 1:08 pm

    This steak looks amazing! I know a few boys who are going to love it!

    Reply
  12. Krista says

    Posted on 5/22 at 9:50 am

    My hubby will go crazy over this! I have to make it for dinner soon!

    Reply
  13. Karlynn says

    Posted on 5/22 at 9:46 am

    This looks like an epic date night dinner recipe. Saving this for later.

    Reply
  14. Lee says

    Posted on 5/21 at 10:18 pm

    Do you think this would work in a crockpot?

    Reply
    • The Chunky Chef says

      Posted on 5/21 at 10:45 pm

      I probably wouldn’t recommend it, as flank steak is pretty easy to overcook and I think the crockpot would do just that.

      Reply
  15. Dorothy at Shockingly Delicious says

    Posted on 5/21 at 9:10 pm

    There are so many great ways to use flank steak! Anytime I can have prosciutto
    I am a happy girl! This looks amazing!

    Reply
  16. Dee says

    Posted on 5/21 at 8:37 pm

    What an amazing dish! Pretty sure my family will love it!

    Reply
  17. Anna says

    Posted on 5/21 at 6:36 pm

    I’ve been looking for a new recipe for a flank steak! This looks incredible!

    Reply
  18. April says

    Posted on 5/21 at 11:16 am

    This is such a delicious way to cook flank steak!

    Reply
  19. Madi says

    Posted on 5/21 at 9:14 am

    Everything about this recipe sounds so good! I love flank steak!

    Reply
  20. Kathryn Godin says

    Posted on 3/6 at 6:13 pm

    Looks amazing. I’m assuming because if the short  cooking time, the prosciutto does not get dried out or hard?

    Reply
    • The Chunky Chef says

      Posted on 3/6 at 8:11 pm

      Thank you 🙂 No it stays nice and tender.

      Reply
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