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Grilled Cheese Sandwiches with Sun-Dried Tomato Pesto

5 stars based on 8 votes

Grilled cheese is my favorite guilty pleasure, and I’m happy to skip lunch so that I can consume an indecent amount of grilled cheese for dinner. That’s especially true with these Italian-style grilled cheese sandwiches zhushed up with sun-dried tomato pesto. My 13-year-old son, Zach, calls them “pizza paninis” since they taste like hot, crispy pizza sandwiches. I serve them with a green salad for a quick weeknight meal; they also make a comforting after school snack for growing teenage boys who suddenly require a pre-dinner ‘dinner.’

ingredients

To make the pesto, combine the sun-dried tomatoes with their oil, garlic, salt, red pepper flakes, sugar, basil, pine nuts, Parmesan and 2 tablespoons of water in the bowl of a food processor fitted with the steel blade.

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Pulse, scraping down the sides as necessary, until the mixture is finely puréed. Note that you’ll have way more than you’ll need; leftover pesto can be frozen or tossed with pasta.

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To make the sandwiches, spread one side of each slice of bread with butter.

buttering-bread

Then flip over and spread the pesto evenly over the other side of each slice.

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Heat a large nonstick or cast iron pan over medium heat. Place the bread, butter-side-down, in the pan. Divide the cheese evenly over the bread, then top the sandwich with the remaining bread.

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Cook until the first side is golden brown, a few minutes. Then, carefully flip the sandwich and cook, covered, until the cheese is fully melted and the bread is golden brown, a few minutes more.

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Let cool slightly, then slice the sandwiches in half and serve. Enjoy!

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Grilled Cheese Sandwiches with Sun-Dried Tomato Pesto

Servings: 4
Prep Time: 10 Minutes
Cook Time: 10 Minutes
Total Time: 20 Minutes

Ingredients

For the Sun-Dried Tomato Pesto (makes 1-1/2 cups)

  • 1 (8.5-ounce) jar sun-dried tomatoes packed in olive oil
  • 2 cloves garlic
  • 1/2 teaspoon salt
  • 1/4 teaspoon crushed red pepper flakes
  • 1/2 teaspoon sugar
  • 1 cup packed fresh basil leaves
  • 1/4 cup + 2 tablespoons pine nuts
  • 1/3 cup freshly grated Parmigiano-Reggiano
  • 2 tablespoons water

For the Grilled Cheese Sandwiches

  • 8 slices Italian bread
  • 4 tablespoons softened butter
  • 8 oz Fontina or Gruyere (or any good melting cheese), sliced or grated
  • 1/2 cup sun-dried tomato pesto

Instructions

For the Sun-Dried Tomato Pesto

  1. In the bowl of a food processor fitted with the steel blade, combine the sun-dried tomatoes with their oil, garlic, salt, red pepper flakes, sugar, basil, pine nuts, Parmigiano-Reggiano and 2 tablespoons of water. Pulse, scraping down the sides as necessary, until the mixture is finely puréed.

For the Grilled Cheese Sandwiches

  1. Spread one side of each slice of bread with butter, then flip over and spread the pesto evenly over the other side of each slice. Heat a large nonstick or cast iron pan over medium heat. Place 4 slices of bread, butter-side-down, in the pan. Divide the cheese evenly over the bread, then top the sandwiches with the remaining bread. Cook until the first side is golden brown, a few minutes. Carefully flip the sandwiches and cook until the cheese is fully melted and the bread is golden brown, a few minutes more. Let cool slightly, then slice the sandwiches in half and serve.
  2. Note: You'll have plenty of leftover sun-dried tomato pesto. It keeps well in the refrigerator for up to 4 days and can be frozen for up to 2 months. You can also try tossing the pesto with pasta; just keep in mind that the pesto is thick so you'll need to thin it with some of the pasta cooking water and a little olive oil when tossing it with the pasta.

Nutrition Information

Powered by Edamam

  • Serving size: 1 sandwich
  • Calories: 646
  • Fat: 54 g
  • Saturated fat: 22 g
  • Carbohydrates: 21 g
  • Sugar: 2 g
  • Fiber: 1 g
  • Protein: 20 g
  • Sodium: 733 mg
  • Cholesterol: 98 mg

Reviews & Comments

  • 5 stars

    Pronounced the BEST grilled cheese EVA…according to my 15 and 13 year olds! I wasn’t sure if they would like this version but WOW…both kids asked for it two nights in a row. Super easy to make and tasty. My 56 year old enjoyed it just as much and he is a picky foodie! This will be our fast food on nights where we are pressed for time. Thanks so much Jen!

    - Christine Chippindale on May 25, 2017 Reply
  • Hi Jenn, in an effort to save some time (with three little ones at home) if I were to use store bought pesto, how much would get mixed with the sun-dried tomato?

    - Jane on February 26, 2017 Reply
    • You could save yourself even more time and just by sundried tomato pesto! (They may have it in your grocery store, but if not, I know Whole Foods carries it.) You also could just use regular pesto here- it’ll still be delicious!

      - Jenn on February 28, 2017 Reply
  • 5 stars

    Wow! Wow! and Wow! Of course I oven grilled it on baking paper (no mess less fuss) and substituted the pine nuts for a combo of pumpkin seeds, sunflower seeds and popped quinoa, but that is seriously the best grilled cheese sandwich I have ever tasted! Taking the lead from other feedback back here I have frozen the additional pesto and will enjoy that later in the year with tomato soup. Like every other recipe of yours that I have tried and tasted – its a winner and a keeper :) Thank you so much for sharing your talent, from amazing soups and mains, to deserts and toasted sandwiches, your efforts are genuinely appreciated!

    - Sandra Quigley on February 23, 2017 Reply
    • 😊 So glad you’re enjoying the recipes, Sandra!

      - Jenn on March 8, 2017 Reply
  • 5 stars

    Just prepared this tonight as I purchased a food processor due to be inspired by your website and wanted to try it out. It was absolutely wonderful! Looking forward to making it for lunch tomorrow again!

    Thank you!!!!

    - Jesse on January 30, 2017 Reply
  • 5 stars

    Made these last night – absolutely scrumptious!! Another terrific recipe – thanks Jenn!!

    - Tamera on January 26, 2017 Reply
  • 5 stars

    Made this for dinner last night and paired it with the Classic Tomato Soup. It was delicious and the perfect comfort food on a cold and rainy January night.

    - Tracy on January 24, 2017 Reply
  • Thank you for yet one more absolutely delicious recipe! My family LOVED these sandwiches; and my son said that your son was spot on with his description of them! Thank you so much for bringing us all such wonderful cuisine!

    - DD on January 24, 2017 Reply
  • 5 stars

    This is another great recipe idea from Jenn! Satisfying, quick meal and the delicious home made pesto turns it into more than a plain grilled cheese sandwich. One mod I tried was putting in a slice of cooked bacon with the cheese. Pretty tasty. Served them with spears of crunchy dill pickles on the side. I used a 8 inch iron skillet on medium for the first one, but medium on my electric range was too hot. The bread toasted dark before the cheese melted all the way, even with a cover. So now I cook on medium low with much better results.

    - Duffy on January 23, 2017 Reply
  • What’s the calorie count . I hate to ask, kind of like if you have to ask you can’t afford to eat it.

    - Lee Ann on January 23, 2017 Reply
    • Hi Lee Ann, Nutritional data is below the recipe now – sorry it was missing! For what it’s worth, I think it’s worth the splurge :).

      - Jenn on January 23, 2017 Reply
  • Have you ever subbed the pine nuts for walnuts? Would it work with this recipe?

    - Kristen on January 23, 2017 Reply
    • Hi Kristen, I definitely think walnuts would work here. Please let me know how it turns out if you try it :).

      - Jenn on January 23, 2017 Reply
    • I use pistachios instead of pine nuts when I make pesto (sicilian version)

      - Janet on January 23, 2017 Reply
  • 5 stars

    Is it possible to just omit the nuts in the pesto? I have a family member who is allergic to all nuts. The sandwich is great without it but would love to be able to try a non-nut version if possible.

    - Celeste on January 22, 2017 Reply
    • Sure, Celeste, but I would add 1/4 cup more cheese.

      - Jenn on January 22, 2017 Reply
    • I have a son that has nut allergies. When I make pesto, I substitute roasted sunflower seed kernels for nuts. It’s just as delicious!

      - Leah on January 23, 2017 Reply
    • 5 stars

      Thank you for the suggestions will try both!

      - Celeste on January 23, 2017 Reply

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