Italian Stuffed Flank Steak

Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese… flavorful steak medallions that are tasty as they are good looking!

Where’s the beef?  I’ve been all about posting the chicken recipes here lately, so I though it was time for some red meat!  This Italian stuffed flank steak may look fancy, but it’s not all that difficult to make.  Actually it’s kind of fun!  Plus, as a bonus, you’ll look like a rockstar to whomever you serve these to!!

Italian Stuffed Flank Steak | Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking! |

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 steak recipe.  It’s a great twist on a regular grilled steak.


It may look complicated, but trust me, it’s not 🙂  It uses flank steak, which I’ve used before in my Asian Beef with Snap Peas, and my Mongolian Beef… I love it for it’s versitality and good price tag.

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.

Now you’re going to need some wax paper and either a hammer or a meat tenderizer tool.  I don’t have a fancy tool like that, so my husband let me borrow this… it got the job done lol.


Be careful when pounding the steak, you don’t want to break holes in the steak… just make it thin

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.

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.


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



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.  Grab some kitchen twine and tie up the steak in one inch intervals until your steak looks something like this…


Look at those layers in there... pure deliciousness!

Look at those layers in there… pure deliciousness!

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.


I’m not one for eating raw meat… but seriously… that looks super yummy!!!

If it was warmer, I’d probably send these outside with my husband to be grilled to perfection, but since it’s winter in Ohio, there’s noooooo way we’re grilling.  So instead, I seared them in my cast iron pan, and then slid the pan into the oven to finish cooking.  It worked really well!!

Now these babies 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.  It’s the same glaze I used in my Chicken Caprese, and seriously… wow you guys… it’s heaven in a bottle!!

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

I’m telling you… these wow’ed my family!  Even my kids scarfed these down… it’s not every day I can get my picky 5 year old to eat steak, so I was pretty excited 🙂

Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking!

Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking!

I love to serve these with a big bowl of my 3 ingredient slow cooker ranch mushrooms and some super crispy baked parmesan and garlic potato wedges!

Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking!

Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking!

Recipe adapted from Kathrynannew

Italian Stuffed Flank Steak | Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking! |
5 from 7 votes
4 servings
Italian Stuffed Flank Steak
Prep Time
20 mins
Cook Time
15 mins
Total Time
35 mins
Tender flank steak rolled up with garlic, herbs, prosciutto ham, provolone cheese... flavorful steak medallions that are tasty as they are good looking!
Calories: 602 kcal
Author: The Chunky Chef
  • 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
  1. Combine garlic, shallot, parsley, basil, sage, and olive oil in small bowl.
  2. 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.
  3. Lay prosciutto evenly over steak, leaving 1-inch border along top edge.
  4. Cover prosciutto with even layer of cheese, leaving 1-inch border along top edge.
  5. 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.
  6. 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.
  7. Using a sharp knife, slice roll between pieces of twine into 1-inch-thick pinwheels. Season pinwheels lightly with salt and black pepper.
  8. Skewer each pinwheel with a toothpick.
  9. Preheat oven to 350.
  10. 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.
  11. Slide skillet into preheated oven and cook for about 8-10 minutes or until steak reaches desired doneness.
  12. Remove from oven, tent with aluminum foil and let rest for 5 minutes.
  13. Remove twine and toothpicks and enjoy!

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79 comments on “Italian Stuffed Flank Steak”

  1. Ohhhhhhhhhh man. Another amazing recipe. I LOVE the balsamic drizzled on top- it makes it look so gourmet 😉 I’ve always wanted to make this… I agree, it would be awesome on the grill in the summertime too! MMMM. I’ll let you know how it comes out when I try it, yum!

  2. These look amazing! Would be a great to treat your Valentine!

    • Thank you!!! You’re right, this would definitely make a great Valentine’s Day dinner 🙂 Add some wine, candles and a yummy dessert and you’ve got yourself a perfect night in 😀

  3. Looks amazing! Love how this turned out and the the flavorful layers! This just made my dinner list! 🙂

  4. Wow! That looks amazing and you make it look simple to make. I need to try making this stuffed Flank Steak! Yummy . I’m pinning it. Also, following all your social medias. I have to keep up with your delicious recipes!!!

    • Thank you!! I’m always worried that I make things look more complicated than they actually are, so I’m glad I didn’t do that here 🙂 The follows and pins are so appreciated!! Following back 🙂 🙂

  5. This looks so good right now, and we just had dinner! 🙂

  6. Oh, that looks delicious! My kind of dinner. I’m pinning this! (found you on Thursday Favorite Things). Hugs

  7. What a lovely dinner party worthy dish!! Perfect for our fiesta today too. I LOVE all of that garlic-herb-shallot goodness spread all over the meat- delicious!! I know the feeling about trying to wow the picky eaters in the family…. My 8 year old is super picky too- it so exciting for me when something new, tasty, and gourmet is approved by her palate!! Congrats on winning your 5 year old over! 😉 Happy Fiesta Friday!

    • Thank you so very much!!! Yeah that garlic, herb, and shallot spread is my favorite part too… I want it on everything 😀 I feel for you on the picky eater thing… it’s so funny how they can be so stubborn and picky one minute, then absolutely devour something new the next 😉 Happy FF!

  8. …..I think I know what’s going on the V Day menu!!!!! AMAZING!

  9. Wowee Amanda!! this looks phenomenal!! I wish I had some flanksteak in my fridge to make this tonight!
    This is going on my lists to make soon. i know it will be a HUGE hit! 🙂

  10. Oh, wow! This looks delicious!

  11. YUM! It looks so fancy too, but seems so simple to make!


  12. wow! I don’t eat steak very much, or really at all, but I think I’m gonna have to try these – they’re literally making my mouth water!

  13. Beautiful recipe. The idea is very good. Thanks for sharing

  14. I don’t know which looks better, the Spanish chicken or this! Both! I had to laugh because most people I know are perfectly happy the littles don’t want their steak! 🙂

  15. Thank you for joining us on #PureBlogLove last Thursday, we are pinning and sharing on our social media! Please join us Tonight at 8 PM EST- Monday Morning to celebrate!

  16. Congratulations!! Your recipe has been featured at Tickle My Tastebuds on my blog, Lori’s Culinary Creations. Hop on over and grab a feature button and link up your latest culinary creations. Congrats again.


  17. Dang girl! I just found this! Wow and yum! I can’t wait to try this. Pure genius!!

  18. I have a question about your recipe. Can this be done in the oven, without using a cast iron skillet? I don’t own one, but really want to try this recipe.


    • Hi Jennine! Sure, I think it could be adapted. Here’s what I would do… place a baking sheet (one with a rim) in your oven and preheat it to 350, so it gets nice and hot. While it’s preheating, go ahead and sear your steaks on both sides in a regular skillet. Then once the oven and baking sheet is preheated, place the steak pinwheels on the baking sheet and bake for 8-10 minutes (or however “done” you like your steak). Pull the baking sheet out and loosely cover the steaks with aluminum foil for 5 minutes. That should do the trick 🙂

  19. OMG this looks so delicious! I love flank steak but have never made it this way.

  20. YUM – These look so good. Cannot wait to give them a try! Prosciutto, balsamic and beef – Pined!

  21. What is the sauce in the picture? Balsamic glaze? Can you share recipe please?
    Looks sooo good!

    • Thank you Nicole! It’s a balsamic glaze that I bought from my grocery store… that way I always have it on hand. If you wanted to make your own, just heat about 2 cups of balsamic vinegar and 3/4 cup brown sugar in a small sauce pan over medium heat. Whisk until the sugar is dissolved, bring to a boil, then reduce heat to low and simmer for about 20 minutes (until the mixture is reduced by half). Add 1 Tbsp butter and let it dissolve, stir into the sauce. It will thicken up and should be a consistency that will coat the back of a spoon. You can either use it right away, or let it cool, pour into a jar with a lid, and refrigerate it. 🙂

  22. what did you serve with this??

  23. Made this tonight! It was easier than it looked and a definite keeper! Will make it again so One~maybe Valentines Day!

  24. Made this tonight almost exactly as recipe calls *changes: sautéed in real butter and leftover bacon grease, sub fresh sage for a bit of powder, added a pinch of onion powder for the spread* made balsamic glaze for topping. Cooked after brown for 7 minutes but meat came out at 120 degrees so went for 1 more minute…when served it was med-well. I don’t eat meat, so husband was tester, although he loved it (and he’s very particular) he said it may have been a bit bland without the balsamic. Next time I will marinate the meat before rolling for a bit more flavor. (either Kahlbi or Italian) This was super easy and beautiful, I will absolutely make this for guests! Thank you for a great recipe…I’m visiting your site regularly for new, beautiful, tasty foods to serve 🙂

    • Hi Shoni! 🙂 I’m SO happy to hear your husband loved the steak!! I love your changes, especially the cooking it in butter and leftover bacon grease… and your idea to marinate the meat ahead of time is a great one as well 🙂 Thanks for taking the time to comment 🙂

  25. Greatest ever dam good put on the grill even tho its winter turned out great!!!!!!

  26. Help please! When you slice the flank into 2 pieces, do you prep both pieces or or just 1? Making this for dinner and can’t wait!

  27. Amanda,
    I had to try this today, and because I have no patience I made a few substitutions but I must say it was amazing the way I made it and makes me want to try your original recipe even more. My son is super picky too (even more at 31) so I had to leave the spread off for him but he liked them a lot too, said I could make them again. My husband not so hard to please but very vocal when he does like something.

    • Hi Christine 🙂 I’m SO happy to hear that you loved these!! I’m sure your substitutions were awesome… sometimes the changeups are a real treat 🙂 Glad to hear I’m not the only one dealing with picky children lol. Thanks so much for stopping by to comment 🙂

  28. I loved it

    It was easy and it taste delicious !!

  29. Hi ? These looks super delicious!! i want to make them tomorrow. could you please tell me at what temperature would you grill them and for how long? i prefer my steak medium my husband likes his rare, look moo rare lol. do you think these would be good rare? or since they are stuffed should it be a little more done? thank you so much!!

    • Hi Dorothy 🙂 I think these are good, no matter what level of done-ness you prefer… so if you wanted to cook your husband’s to rare and yours to medium, that would work well. I would start the steaks over direct medium-high heat until they’ve seared on both sides, then move them to a cooler section of your grill to continue cooking slowly. I can’t really give exact times, as every grill is different, so I highly recommend using a meat thermometer to tell when the steaks are done. For rare, go for 115 degrees F for rare, and 130 degrees F for medium. Be sure to let them rest for 5-10 minutes before digging in to ensure they’re nice and juicy 🙂 Good luck!

  30. I made this for dinner last night. It was delightful! I felt like I was eating at a fancy restaurant. It is definitely going in my rotation! My 8yo says its her favorite meal ever (we made it with the oven fries). I cooked it in the oven, but I can see how the grill would take it to a whole new level! Not to mention I can’t sear anything with out smoking the family out of the house. I wish I’d have had the fore thought to do mushrooms too! Sigh. I did not have the balsamic glaze. I think what I liked most was the herbed oil and I think it would be delightful as a marinade for steak bites and mushrooms – so I think I might try that next time. But this was fantastic! Thanks!

    • Hi Heather 🙂 I’m SO very happy to hear that you all loved these steaks!! And I really love that your 8 year old gave it high praises… such a wonderful thing 🙂

  31. Just made this last night. Delicious! Shared pics and recipe with friends who now want to try this. I’ve tried many stuffed flank steak recipes and this one is both delicious and easy to make. Cutting it up into medallions makes the cooking quick and easy. I deglazed the pan with some water and red wine for a delicious au jus. Thank u for the recipe!

  32. Do you think I could make these in advance? Browning them in a skillet the day before then putting them in the fridge until I am ready to cook them the next day?

  33. Do you think I can substitute Ham for the prosciutto?

  34. Great recipe, I did tweak it to make it work for what I had on hand; and I was too lazy to grill individually so I roasted the whole thing and then broiled it for a few…definite keeper! I even made the balsamic reduction!

  35. We made this last night and it was delicious. One thing – we sauteed it for the 3 minutes and then 2 minutes, but baked it at 250 degrees for 5 minutes and it was definitely done. Maybe I flattened the steak too thin, but 350 for 15 minutes it would have been way over cooked. Thoughts?

  36. This was so good. I don’t normally leave a comment but I had to on this one. Thank you for a great recipe. I will definitely be making this again. We loved it. 🙂

  37. I beat the heck out the flank steak and have this all rolled up and waiting for dinner tonight. I cant wait to try it the balsamic drizzle!

  38. Thank you, thank you, thank you for this wonderful recipe! Made this for a special birthday yesterday. Started with a 4lb flank steak to feed 7 people and ended up with nothing left except 7 very happy party goers! So easy to make and you can even make it ahead of time. Thanks again!

  39. That was an amazing dish. I love my steak rare, so it was perfect. Thank you!!! Sharing!

  40. This was absolutely amazing! My boyfriend loved it!!!

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