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Skirt Steak Sandwiches with Pesto
and pineapple spears

Active: 40 minTotal: 40 min

Thanks to leftover pesto made earlier in the week, this meal is a breeze to put together on a weeknight. This meal was first featured in 2017, but we've added an extra step to marinate the meat, which will make it even more tender and flavorful.
Smarts: If you're cooking the steak on the grill, leave it whole. If cooking on the stovetop, thinly slice it before cooking so that it cooks quickly.
Smarts: The pineapple spears served on the side of this meal can be served fresh, but for a different twist, they are also great grilled. Searing the fruit caramelizes its natural sugars.

Tags

Ingredients

Servings:
4
Metric
Grilled Pineapple Spears:
  • Pineapple, fresh - 2 lbs, sliced into spears
Basil Pesto:
  • Pine nuts - 2 Tbsp (sub walnuts or pecans)
  • Garlic - 1 clove, peeled
  • Cheese, parmesan (opt) - 1 oz, grated
  • Basil, fresh - 1 1/2 oz
  • Lemon juice - 2 tsp
  • Oil, olive - 3 Tbsp
Skirt Steak Sandwiches with Pesto:
  • Oil, cooking - 2 Tbsp
  • Soy sauce, low-sodium - 2 Tbsp
  • Vinegar, red or white wine - 1 Tbsp
  • Steak, skirt - 1 lb (sub flank, hanger, flat iron)
  • Onions, medium - 1, sliced
  • Bell peppers, yellow or orange - 2, sliced into 1" / 2.5 cm wide pieces
  • Rolls, like ciabatta or sandwich - 4 (sub baguette)
  • Pesto (ingredients listed separately) - ~1/4 cup

Nutrition Facts

Serving Size: 1 serving
Servings Per Recipe 4
Amount Per Serving
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% Daily Value
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Prep

  1. Marinate steak - (If prepping right before cooking and using a grill, get grill heating while steak marinates.) Combine cooking oil, soy sauce, and vinegar. Add steak and turn to coat in marinade. Tenderize with a fork. Marinate for 30 minutes and up to one day. (Can be done 1 day ahead)
  2. Make pesto - (Skip if made ahead for Monday.) Toast nuts in a dry skillet or frying pan until fragrant and golden, 3 to 4 minutes. Peel garlic cloves. Place nuts, garlic, parmesan cheese (if using), basil leaves, and lemon juice in a food processor. Pulse until all ingredients are well chopped. With food processor running, drizzle in olive oil until smooth. (Add some additional olive oil if needed to help everything blend.) Season to taste with some salt and pepper. (Can be done up to 5 days ahead)
  3. Onions / Bell peppers - Prep as directed and combine. (Note: If cooking on the grill, you'll want to use a grill basket or slice these large enough that they will sit on the slats of the grill.) (Can be done up to 5 days ahead)
  4. Pineapple - Slice into spears. Use this video to see how to peel pineapple. (Can be done up to 4 days ahead)

Make

  1. Remove steak from marinade (discard marinade). Season steak with some salt and pepper. If cooking on the stovetop, thinly slice steak against the grain.
  2. Slice rolls open. (If using baguette, slice open through the center lengthwise and divide into portions to make sandwiches.)
  3. If cooking on the stovetop: Heat a wok or skillet over medium-high heat. Add some cooking oil and then peppers and onions. Saute until nearly tender, ~5 minutes. Add steak and saute until steak is just cooked through, ~4 minutes more. Toast bread.
  4. If cooking on a grill: Heat grill to 500F / 260C degrees and clean grates. Brush peppers and onions with some olive oil and sprinkle with some salt. Arrange steak, peppers, onions, and pineapple on grill (use a grill basket for the peppers and onions if you have one or place them on a piece of foil on the grill to prevent them from falling through the cracks). Grill uncovered - steak for 2 to 4 minutes, peppers / onions for 4 to 6 minutes, and pineapple for 2 to 3 minutes - per side for all ingredients. Toast bread on the grill in the last 2 minutes of cooking.
  5. {grill}: Set steak aside, covered, and let rest for 10 minutes. Thinly slice against the grain.
  6. Assemble sandwiches by slathering on pesto and layering in sliced steak and peppers / onions. Enjoy with pineapple spears on the side!

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Reviews

This meal has 14 reviews

A little on the bland side. Could maybe use more spice with the veggies. Could be because I didn't make this on a grill.

By: Ryan
Posted: Aug 04, 2019
Diet: Vegetarian

The sandwich was a little messy but the flavor was good. I had leftover pesto from a previous Cooksmarts meal in my freezer, so this turned out to be a pretty quick meal.

By: Melissa
Posted: Aug 03, 2019
Diet: Original

It's fine but kind of boring. Some parmesan cheese melted over the veggies probably would have helped.

By: Chelsea
Posted: Aug 03, 2019
Diet: Vegetarian

We really enjoyed this! Made the “paleo” version which for us was just the original but without bread and more meat. Funny thing is, as we ate the steak and the veggies we kept thinking “wow, this would make a really good sandwich.” If you’re cooking on the stove you’ll probably need to split everything into two batches (with the steak and veggies combined for flavor, don’t cook just the veggies followed by just the steak!) unless you have a much larger pan than I do.

By: Summer
Posted: Jul 29, 2019
Diet: Paleo

Steak should probably be cooked separately from the onions and peppers if you are going to use a wok. Other than that, great recipe!

By: Brian
Posted: Jul 27, 2019
Diet: Paleo

Good, but a little time consuming. I should plan ahead and do the prep next time. Great way to show off the grill!

By: Julia
Posted: Jul 26, 2019
Diet: Gluten-free