Italian Stuffed Steak Pinwheels: An Elevated Entree

When I think of pinwheels of the edible variety, I tend to think of the cold pinwheel sandwiches that are made with deli meat and cheese, and wrapped up in a tortilla.

Vertical image of two slices of a rolled beef dish with a salad and potato sides on a plate, with text on the top and bottom of the image.

Those are more of a snack food, I know.

However, this kind of pinwheel recipe is a totally different story.

Flank steak is one of my favorite cuts. I love how it soaks up marinades so beautifully, and tastes like buttery perfection straight off the grill.

Thankfully, a flank steak is just the cut of beef to use for this magical Italian-themed recipe.

Perhaps at some point you have come across this type of beef-based pinwheel at the meat counter at your local butcher shop or grocery store.

They are so gorgeous that they do tend to draw the eye, especially if your belly is rumbling in anticipation of dinner.

Vertical image of a white plate with slices of a rolled beef dish filled with basil and melted cheese.

The truth is, these usually cost a lot of money at the store. And they are sometimes stuffed with ingredients that my husband and I aren’t super pumped about (mushrooms for him, and olives for me), so usually I opt out of buying them premade.

After all, why buy something that you can easily make at home yourself, less expensively and customized to your own tastes?

Yes, you read that right – when I say easily, I truly mean this recipe is easy to prepare.

Really, all you are doing is butterflying the steak, topping it with a few straightforward ingredients (no chopping required), and rolling it up. Then all you have to do is throw it on the grill to cook it up.

This entree has become a treasured favorite for grilling season and everyone who comes over is always impressed. The little wheels, oozing slightly with cheese and fresh green herbs, are quite eye-catching.

Vertical top-down image of two plates with pinwheels of steaks, arugula salad, and fries next to red and white towels, silverware, and a glass of red wine.

But it’s really the tasty aroma that wins everyone over. As soon as you cut into the grilled meat to make the pinwheels, you get a whiff of fresh basil and balsamic mingling with the wafting scent of freshly grilled steak that’s already on the air…

It tickles your nostrils and your mouth starts watering almost immediately.

You can also serve this decadent main dish with so many different side options. As you see here, I like to do a steak frites take on the dish, pairing it with homemade oven fries and a fresh salad of arugula dressed in a dijon vinaigrette.

These pinwheels are also wonderful with roasted or mashed potatoes, asparagus, green beans, or any grilled vegetables you can think of. I mean, you already have the grill on, so why not make the most of it, right?

Vertical close-up image of two rolled beef medallions filled with basil and cheese on a white plate next to arugula and seasoned fries.

The most valuable piece of advice that I can give you for this particular recipe is to make sure the meat rests for at least five to 10 minutes once it is off the grill.

If you cut into it too soon, all those lovely juices will seep right out. You’ll lose a lot of flavor, and the meat won’t be quite as tender as it would be if you waited.

Give it time to rest, then go ahead and slice into it. Serve the pinwheels on a platter and take in the oohs and aahs from appreciative guests. Go ahead, bask in the glory for a little bit.

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Horizontal image of a white plate with rolled beef medallions next to arugula and fries.

Italian Stuffed Steak Pinwheels


  • Author: Meghan Yager
  • Prep Time: 15 minutes
  • Cook Time: 20 minutes
  • Total Time: 35 minutes
  • Yield: 4 servings 1x

Description

Italian stuffed steak pinwheels are filled with the flavors of balsamic vinegar, provolone, and basil. Grilled to perfection, they’re sure to be a hit.


Scale

Ingredients

  • 1 1/2 lbs flank steak, butterflied
  • 1/2 teaspoon salt
  • 1/2 teaspoon freshly ground black pepper
  • 2 tablespoons balsamic vinegar
  • 34 slices deli-style provolone cheese
  • 15 fresh basil leaves
  • Toothpicks

Instructions

  1. Preheat grill to medium-high heat.
  2. Open steak and lay flat, with the grain running from left to right. Sprinkle both sides with the salt and pepper.
  3. Drizzle balsamic vinegar on top, distributing it evenly. Place cheese slices on top, then cover the cheese with basil leaves.
  4. Starting at one of the short ends, begin to roll the steak away from you, rolling it up very tightly. Secure with toothpicks.
  5. Place steak on grill, and reduce heat to medium. Cook for a total of 20 minutes, turning in 5-minute increments to cook on all sides. The internal temperature should read 130˚F for medium rare, or 140˚F for medium well.
  6. Let rest for 5 minutes, then slice into pinwheels and remove toothpicks. Serve immediately.

  • Category: Steak
  • Method: Grilling
  • Cuisine: Beef

Keywords: steak, Italian, balsamic vinegar, provolone cheese, basil, grill

Cooking By the Numbers…

Step 1 – Butterfly Steak, Preheat Grill, And Measure Remaining Ingredients

Butterfly the flank steak.

You can ask your butcher to butterfly the steak for you, or do it yourself at home.

Horizontal image of a butterflied flank on a cutting board next to sliced provolone cheese and dishes of seasonings.

To do this, lay the steak flat on a cutting board, and get out your boning knife or another thin, sharp knife.

About halfway through the thickness of the meat, cutting parallel to the cutting board, you’re going to slice from long end to long end, keeping a hinge on one side where the steak is still attached so the final result opens up like a book.

 

You can use your non-dominant hand as a guide while you slice, holding your palm flat on the surface of the meat to keep it in place when you start, and then opening up the “book” as you go.

Work slowly and carefully if you need to, to avoid cutting unevenly or accidentally poking any holes in the beef.

Preheat your grill to medium-high heat.

Measure out all of the remaining ingredients as listed on the ingredients list.

Step 2 – Season and Fill Steak

Season both sides of the steak with the salt and pepper.

Horizontal image of shingled provolone cheese slices on top of a thin slab of raw beef on a cutting board.

Lay the steak out flat, opened like a book.

Horizontal image of whole basil leaves on top of shingled slices of provolone on top of a thin slab of raw beef on a cutting board.

Drizzle balsamic vinegar over the steak.

Top the vinegar with the slices of cheese. Top the cheese with the basil leaves.

Horizontal image of a rolled log of raw beef held together by toothpicks on a cutting board.

Beginning at one of the short ends, roll the steak up tightly. Secure it with toothpicks.

Step 3 – Grill Steak

Place the steak on the grill, and reduce the heat to medium. Cook for about 20 minutes, turning every 5 minutes or so to cook on all sides.

Horizontal image of grilling a log of rolled beef held together by toothpicks.

The steak is done when the internal temperature is 130˚F for medium rare or 140˚F for medium well. Use a meat thermometer to check for doneness, and keep an eye on it while it cooks.

Step 4 – Slice and Serve

Remove the stuffed steak from the grill and let it rest on a cutting board for 5 minutes. Slice into pinwheels and serve.

Horizontal image of a white plate with slices of a rolled beef dish filled with basil and melted cheese next to a glass of wine.

Please, Oh Please, Remember the Toothpicks…

What’s one of the biggest mistakes you can make? It isn’t over or under cooking the meat. It’s forgetting to take out the toothpicks.

Horizontal image of a white plate with rolled beef medallions next to arugula and fries.

While it might seem obvious to most, sometimes the toothpicks can get buried into the steak a little more with all the turning on the grill. Take your time and make sure you have pulled every single one out before serving.

Personally, I like to count them as I insert them. That way I can make sure I have the same number that I started with, all removed at the end.

For more grilled dishes to get fired up about, check out these entrees from Foodal to try next:

What side dishes will you pair with these pinwheels? Tell us in the comments below. Once you try the recipe for yourself, be sure to come back and rate it!

Photos by Meghan Yager, © Ask the Experts, LLC. ALL RIGHTS RESERVED. See our TOS for more details. Originally published on July 15, 2012. Last updated: September 4, 2020 at 18:37 pm. With additional writing and editing by Allison Sidhu.

Nutritional information derived from a database of known generic and branded foods and ingredients and was not compiled by a registered dietitian or submitted for lab testing. It should be viewed as an approximation.

About Meghan Yager

Meghan Yager is a food addict turned food and travel writer with a love for creating uncomplicated, gourmet recipes and devouring anything the world serves up. As the author of the food and travel blog Cake 'n Knife, Meghan focuses on unique foodie experiences from around the world to right at home in your own kitchen.

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