Stuffed Rolled Flank Steak

Super thin, well-marinated flank steak slices are rolled up around a mix of cheeses, garlicky spinach, and little bits of sun-dried tomatoes for a meal that looks gorgeous and tastes even better. These steak pinwheels make a plain piece of beef look fancy enough for a party, but they're easy enough for any Saturday night at home. When you cut into them, you'll see those pretty swirls of filling—soft cheese, tender beef, and pops of Mediterranean flavor in every bite.

Mouthwatering Flip

• You can prep these rolls the night before, so entertaining is a breeze and you still get to wow everyone with something special
• Slice pinwheels thinner for killer starters, or keep them bigger for a main dish that’ll catch everyone’s eye
• Cheesy, juicy, beefy bites just hit that crave-able, umami spot meat fans dream about
• Make a simple flank steak feel like a five-star meal—it looks super impressive, even picky eaters will gush

First time I made these, it was for my husband’s birthday after spotting something similar in a fancy steakhouse. The way he lit up when I served them was the best part! It started as a one-time experiment but now we make them for every big family event. Even my father-in-law, who never says much, called them “the best meal he’s had in forever” and asks for them every time we get together.

Top-Notch Elements

• Sun-dried tomatoes: add bursts of sweet-tangy flavor throughout. Use the oil-packed kind—they mix in best
• Spinach: brightens things up with color, nutrients, and a little earthy taste to even out the cheesy beefiness
• Swiss cheese: melts into gooey, nutty pockets—Gruyère is a great alternative
• Dijon mustard: gives a little heat and helps everything stick together for a good coating on the steak
• Worcestershire sauce: brings tangy, savory depth that bumps up marinade flavor with just a splash
• Red wine: tenderizes the steak and adds loads of flavor—choose one you’d actually drink
• Soy sauce: delivers that deep umami punch and softens the meat fibers. Go for low-sodium if possible
• Olive oil: makes the marinade rich and helps the steak cook up tender—extra virgin for the biggest taste
• Flank steak: when sliced right, it’s both tasty and just tender enough for rolling—look for even thickness and good marbling

Uncomplicated Method

Rest & Slice:

Once you pull the steak from the oven, cover it loosely with foil and walk away for 10 minutes to let those juices settle back in. Carefully snip off all twine or grab out the toothpicks (don’t miss any!). With a sharp knife, slice into thick pinwheels so everyone gets that beautiful swirl in every bite.

Bake It Up:

Drop the steak in your hot oven (350°F, middle rack) and roast without any cover for about an hour or so, depending how thick your roll is and how you want your steak done. Check the thickest part with a meat thermometer—look for 145°F for pink and juicy, or 160°F if you want it cooked through. The outside gets all browned and the inside stays tender.

Rolling Time:

Put the steak with a short end toward you. Roll it up nice and snug, sort of like a jelly roll, pressing just firmly enough so the filling stays put. Tuck in any filling that tries to escape. Tie it tightly every inch with soaked twine or use toothpicks (soak first so they don’t burn). Flip the roll so the seam side is down in your greased pan to lock it all together.

Layer Your Fillings:

Sprinkle on two cups spinach leaves, a cup of shredded Swiss, a handful of grated Parmesan, chopped sun-dried tomatoes, plus some breadcrumbs and diced onion—layer everything gently so it covers the meat. Use your hands to gently press the cheese and toppings so they don’t slide out while rolling.

Garlic Smash:

Mash garlic with coarse salt (about four cloves and half a teaspoon) into a squishy paste right on your cutting board. Smear this mellow, juicy garlic mix all over the top of your pounded steak, edge to edge, so there’s lots of flavor in every slice.

Baking Prep:

Set your cold steak out about half an hour before cooking so it won’t cook unevenly. Put a little cooking spray in your roasting pan. Pat the meat totally dry (helps it brown better) and toss out any leftover marinade before you put the steak in the pan.

Soak & Marinade:

Drop your trimmed steak into a zip bag or a glass dish. Pour the marinade on top so the meat’s covered. Push out extra air and seal it up. Stash in the fridge at least 8 hours or overnight, turning it when you remember. This makes it super flavorful and extra tender by morning.

Pound and Score:

Put steak between plastic wrap or parchment. Smack it with a meat mallet (or use a heavy pan if you don’t have one) until it's about half an inch thick and even all the way. Score the surface with shallow crisscross cuts so flavors soak in deep, but don’t cut all the way through.

Marinade Mix:

Pour together a good amount of olive oil, soy sauce, red wine, Worcestershire, Dijon, lemon juice, minced garlic, Italian seasoning, and ground black pepper in a bowl. Whisk like crazy so it turns creamy-looking. This helps the steak soak up all the flavor into every bite.

Must-Know Details

• Let the steak warm up a bit out of the fridge before baking so the cooking’s even
• Totally dry your steak after it’s done marinating or it won’t brown up nicely
• A good rest after cooking stops all the juices from gushing out when you cut it
• Scoring the steak before marinating helps the flavors really get in there—and rolling it is way easier
• Twine beats toothpicks for holding everything together, so your pinwheels stay nice and tight

Pin it

The first batch I ever made, I decided to brush a little extra olive oil over the top. Did it help? You bet—it gave it the most amazing golden crust! Even my super picky daughter loved them so much she asked for more and wants these for her birthday now. Watching the cheese melt into creamy pockets along the roll is the best part—there’s just nothing like it.

Showstopping Finish

Fan your steak pinwheels out over super creamy mashed potatoes, let the juices run wild. That swirl design makes everyone at the table stop and stare. For a fancier dinner, pair with roasted asparagus and a zigzag of balsamic glaze to take it up a notch. Or, slice ’em thinner and pop pieces on a pile of polenta for crowd-pleasing appetizers you can eat in two bites.

Fun Twists

Try swapping out the cheeses and herbs—feta, basil, and Kalamata olives for some Greek flair. Go for a southwestern vibe and use pepper jack, taco seasoning, and roasted poblano peppers inside. If you want a steakhouse classic, pack it with blue cheese, crispy bacon, and some sautéed mushrooms for big flavor. Breakfast version? Tuck in scrambled eggs, cheddar, and crispy hash browns for a brunch everyone will remember.

Smart Storage

Keep leftovers in a container with a lid in the fridge within a couple hours—three days later, they’ll still taste great. Best way to warm them up: pop them in a 300°F oven, cover with foil so they don’t dry out, and reheat about 15-20 minutes till nice and hot. Skip the microwave—makes the beef tough. Got plans? Roll and fill the uncooked steak the night before, wrap it up, and bake fresh the next day for an easy head start.

Pro Tips

• Soak your butcher’s twine so it won’t burn while the steak bakes
• If the steak has thick spots, pound ’em flat before adding marinade to get a smooth, easy roll
• Sear the outside of the steak roll in a hot pan before baking to pump up the flavor
• Slice perfectly: let the roll cool, then chill it a half hour before slicing for neat, no-mess pieces
• Feeling fancy? Pour a splash of red wine and a pat of butter into your pan after baking to make a rich, tasty sauce for drizzling over the pinwheels

Pin it

I started with these pinwheels just to copy a good meal from a restaurant, but now they mean so much more to my family. Anytime we pull these out, even regular nights feel kind of special. There’s something satisfying about turning an ordinary steak into something super elegant with just a few steps. When you slice it open and see that mix of cheese, beef, and colorful filling, it somehow feels both fancy and like home cooking all at once. Whether you want to impress a dinner guest or just want a really good meal, these steak pinwheels totally nail the ‘looks great, tastes better’ vibe without any weird tricks or stress.

Frequently Asked Questions

→ Can I cook these steak pinwheels on the grill instead of in the oven?

Definitely! Fire up your grill to medium (near 350°F) and cook the pinwheel steak for 20-25 minutes, giving it a turn every now and then. Shoot for 145°F inside if you want them medium. Let things rest before you slice it up.

→ What's the best kind of beef for making steak pinwheels?

Grab flank steak if you can—it’s easy to roll and tender once cooked. Skirt steak is a solid backup. Top round can work too, just remember to pound it out pretty thin so it doesn’t get chewy.

→ Can I make steak pinwheels ahead of time?

For sure! Leave your steak in the marinade overnight, then roll it up the next morning. Keep it wrapped up tight in the fridge and let it chill out until about half an hour before it's time to bake. Take it out so it isn't super cold going in the oven.

→ What sides go well with steak pinwheels?

Try roasted taters, greens, or steamed veggies alongside. Garlic mashed potatoes or rice pilaf are great too and soak up those tasty steak juices.

→ Can I swap out the fillings inside the steak pinwheels?

Oh, totally! Go wild—try roasted red peppers, cooked mushrooms, new cheeses like blue cheese or provolone, or even spread some pesto on before rolling.