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Grilled Cheese Sandwiches with Sun-Dried Tomato Pesto

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By Jenn Segal
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What do you get when you combine a classic American grilled cheese with Italian sun-dried tomato pesto? A deliciously crispy and gooey sandwich that delivers bold and tangy “pizza” flavor.

Halved grilled cheese sandwich stacked on a plate.

Grilled cheese is my favorite guilty pleasure, and I’ll happily eat light all day so I can indulge in seconds to my heart’s content at dinner. That’s especially true with these Italian-style grilled cheese sandwiches jazzed up with sun-dried tomato pesto. My kids call them “pizza paninis” since they taste like hot, crispy pizza sandwiches. I like to serve them with an arugula salad or vegetable soup for a quick weeknight meal.

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“Thank you for the best grilled cheese sandwich we have ever eaten! Fontina cheese melts so easily and the sun-dried tomato pesto adds incredible flavor!”

Elaine

What You’ll Need To Make Grilled Cheese with Sun-Dried Tomato Pesto

Sandwich ingredients including basil, crushed red pepper, and butter.

Step-by-Step Instructions

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.

Food processor of sun-dried pesto ingredients including pine nuts, crushed red pepper, and sugar.

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.

Food processor of sun-dried tomato pesto.

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

Knife buttering a piece of bread.

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

Knife spreading sun-dried tomato pesto on bread.

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.

Cheese and sun-dried tomato pesto sandwich in a skillet.

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.

Grilled cheese and sun-dried tomato pesto sandwich in a skillet.

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

Halved grilled cheese sandwich with sun-dried tomato pesto stacked on a plate.

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Grilled Cheese Sandwiches with Sun-Dried Tomato Pesto

Metric Cup Measures
By Jenn Segal

What do you get when you combine a classic American grilled cheese with Italian sun-dried tomato pesto? A deliciously crispy and gooey sandwich that delivers bold and tangy “pizza” flavor.

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
  • ½ teaspoon salt
  • ¼ teaspoon crushed red pepper flakes
  • ½ teaspoon sugar
  • 1 cup packed fresh basil leaves
  • ¼ cup + 2 tablespoons pine nuts
  • ⅓ 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
  • ½ 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.

Pair with

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
Nutritional Data Disclaimer

This website is written and produced for informational purposes only. I am not a certified nutritionist and the nutritional data on this site has not been evaluated or approved by a nutritionist or the Food and Drug Administration. Nutritional information is offered as a courtesy and should not be construed as a guarantee. The data is calculated through an online nutritional calculator, Edamam.com. Although I do my best to provide accurate nutritional information, these figures should be considered estimates only. Varying factors such as product types or brands purchased, natural fluctuations in fresh produce, and the way ingredients are processed change the effective nutritional information in any given recipe. Furthermore, different online calculators provide different results depending on their own nutrition fact sources and algorithms. To obtain the most accurate nutritional information in a given recipe, you should calculate the nutritional information with the actual ingredients used in your recipe, using your preferred nutrition calculator.

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Comments

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  • 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?

    • 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!

  • 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
    • Reply

    • ? So glad you’re enjoying the recipes, Sandra!

  • 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!!!!

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

  • 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.

  • 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!

  • 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.

  • What’s the calorie count . I hate to ask, kind of like if you have to ask you can’t afford to eat it.

    • 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 :).

  • Have you ever subbed the pine nuts for walnuts? Would it work with this recipe?

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

    • I use pistachios instead of pine nuts when I make pesto (sicilian version)

  • 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.

    • Sure, Celeste, but I would add 1/4 cup more cheese.

    • 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!

    • Thank you for the suggestions will try both!

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