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Grilled Cheese Sandwiches with Sun-Dried Tomato Pesto

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These grilled cheese sandwiches with sun-dried tomato pesto taste like hot, crispy pizza paninis.

Halved grilled cheese sandwich stacked on a plate.

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.’

What you’ll need to make Grilled Cheese Sandwiches

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

How to make grilled cheese sandwiches

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

These grilled cheese sandwiches with sun-dried tomato pesto taste like hot, crispy pizza paninis.

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


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


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

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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  • What cast iron skillet do you use or recommend Jen? I have your book but we just moved (immigrated actutally) and it’s still in one of the boxes. Do you have an article with tips for what brands to use? I love your website so much! I’m going to be teaching my kids cooking lessons and we will be using your recipes and ideas. Have a wonderful Christmas! xxx

    • — Samantha on December 2, 2023
    • Reply
    • Hi Samantha, I hope you’re very happy with your new home/country! I have a Lodge cast iron pan and love it. And, yes, I do have several posts with info about my favorite brands. Here’s here’s one on pots and pans, this focuses on knives, and this one’s for baking pans. Hope you find them helpful! 😊

      • — Jenn on December 4, 2023
      • Reply
  • I have to say that out of all of the recipes I use daily from your site, this is my work horse, quick and nutritious go – to recipe that I prepare for my son’s family. I make the sandwiches and wrap them in plastic wrap and all they have to do is grill them up on their George Forman grill.
    I’ve made several variations with cheeses and breads and my favorite is Italian pane de casa whole wheat with fontina. The fontina is just as good as gruyere and not as expensive. I do buy bottled tomato pesto which makes it even easier.
    Always great recipes for real kitchens and real cooks and always has that extra special spin on a dish that makes it gourmet.
    Thanks, Jenn.

    • — Marilyn S on December 1, 2023
    • Reply
  • Hi! Is there someway to covert dried tomatoes into oil packed ones? Just soak in oil, or maybe water first then oil? Every recipe of yours that I have tried has been a huge hit with my family and friends. Thanks so much.

    • — Kathleen on August 10, 2023
    • Reply
    • So glad you like the recipes! I’ve never tried anything like what you’re suggested, so I don’t have much wisdom to share — sorry!

      • — Jenn on August 11, 2023
      • Reply
  • Sooo Delicious! I used a mixture of swiss and gruyere on sourdough with a swipe of the pesto. Can’t wait to make this when my daughter visits. I have a lot of pesto leftover so I froze it in ice cube trays and plan on using it on homemade pasta.

    • — Kim on August 6, 2023
    • Reply
  • 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! Kudos to the “Chef”!

    • — Elaine on May 13, 2023
    • Reply
  • Made these “boujie” (as my daughter calls them) grilled cheeses last night…served with tomato soup…SOOO good!!! Any suggestions on how to use the leftover pesto? Thinking about making homemade pizza tonight and using, but always up for other ideas!

    • — Kristie (Senoia, GA) on August 7, 2022
    • Reply
    • Glad you enjoyed, Kristie! Pizza is a great idea; it’s delicious good tossed with pasta, too.

      • — Jenn on August 7, 2022
      • Reply
  • is there a way to make a batch of these in the oven for a bridge group? I need to make 8 sandwiches and my cast iron skillet will only hold 2 at a time.

    • — Joni on June 26, 2022
    • Reply
    • Sure Joni, I think you could get away with it. I’m not sure about the timing, but I’d flip them halfway through. Please LMK how they turn out!

      • — Jenn on June 28, 2022
      • Reply
  • Next month, I’m helping a local organization with an outdoor party and need to bring a large quantity of finger appetizers. Do you think this would taste good if I put this delicious spread and cheese onto flour tortillas to make sheet pan quesadillas? Theses would be baked, not fried. I’m concerned that part of the “yumminess” of grilled cheese is the butter. Thoughts?

    • Hi Karen, I’m concerned that the whole grilled cheese concept would get a little bit lost in translation if you baked fees. I have lots of finger foods in my appetizer section that I think might work better. You can browse through them here, but a couple that come to mind are:
      Candied Pecans
      Crab Cakes (You can make smaller versions of these so they can be finger foods.)
      Cheddar and Herb Cheese Straws
      Cheese Ball

      Hope you find some options that work for you!

  • This was so good! I added a teensy amount of balsamic vinegar to add a bit of acidity and harissa for extra heat. Highly recommended, delish. Thank you. Your recipes never fail 🙂

  • Made these for a cozy dinner night and these grilled cheese sandwiches with the sun-dried tomato pesto were amazing! My husband just RAVED about these “adult grilled cheeses.” Thank you Jen!!

  • Just got delivered Sun-dried tomato pesto by mistake in my @tescoirl shop, so this is a sure sign as I love toasties..

  • I love grilled cheese sandwiches and this one added a new spin. Loved this and can’t wait to serve it at the next game night for my sister and niece. Thanks for another winner.

  • This was a pandemic comfort food winner! Easy to fix on a weeknight, paired with tomato basil soup. I didn’t have enough basil, so did half basil and half kale and it was delicious! Expect to use the leftover pesto on pasta later this week.

  • I love this sandwich! I am a sucker for a good grilled cheese and pesto! Unfortunately, I am allergic to nuts so pesto is hard to come by so I love making it at home. Although different, I’m sure, I added sunflower seeds instead and still turned out lovely!

  • This sandwich is delicious and a huge hit in our family. It is lovely with soup(s). Thank you Jen!

    • — Damienne Dunham
    • Reply
  • Delicious! I love and trust your recipes. Thank you for doing what you do! Side note, not about this recipe – I received your cookbook just a day or two before my mom was hospitalized last year. Before heading to the hospital to spend the day with her, I put it in my bag. Mom perked right up when I took it out and handed it to her, and we spent hours looking at it and making plans to try various things in it.

    • Glad you liked these! And happy to hear that the cookbook provided a nice distraction while your mom was in the hospital. Hope she’s fine now!

  • According to my 18-y-o son, “These are the best grilled cheese sandwiches ever!” High praise from a serious sandwich eater. I went a little light on my application of the pesto, but I’ll go all out next time–the entire family asked for more pesto. Everyone loved them! Thanks for another great twist on a classic!

  • So delicious!! And the gruyère cheese is the perfect complement! Perfect lunch

  • Hi Jenn,
    Do you spread the pesto on both sides of the sandwich? My daughter is planning to make these as part of a mini-meal 4-H cooking contest. She has already made them a couple of times and they are delicious, but getting the right proportion of cheese to pesto is tricky. How much pesto do you use? Also, any other cheeses you recommend?

    • Hi Amanda, Yes on both sides — and you’ll need about a tablespoon for each slice. As for cheese options, you could try mozzarella or smoked mozzarella/provolone. I have a wonderful pesto and smoked gouda grilled cheese sandwich in my cookbook if you wanted to serve another variation. If you don’t have the book, I’m happy to send you the recipe. Just email me at jennifer@onceuponachef.com. 🙂

  • So good!! The pesto is delicious on spaghetti later in the week!

  • Delicious with tomato basil soup!

    • — Connie Hoffman
    • Reply
  • Can I use sundried tomatoes that are dry (not packed in oil)?

    • Hi Cam, That should work — you’ll need to add oil to the mix too. I’d add the oil directly to the food processor little by little until the pesto looks like the right consistency. I’d estimate you’ll need about 1/2 cup. Hope you enjoy!

  • Hi Jenn,

    I would like to try to make this for a crowd. Do you think several sandwiches could be toasted in the oven instead of cooked individually on the stovetop?

    Thank you!

    • Hi Nooshin, I think these are probably best when pan-fried, but would be doable in the oven. (I’d stick them under the broiler for a minute or two at the end to crisp up the outside of the bread. I’d love to hear how they turn out!

  • Delicious. I love the added flavor the pesto gives to the grilled cheese, and it does taste like pizza.

  • I have sun dried tomatoes but they are not packed in oil. Can I just put them in oil? If so, what would be the ratio of tomato to oil? Thanks

    • Hi Myra, That should work; I’d just add the oil directly to the food processor. You’ll have to add it little by little until the pesto looks like the right consistency. I’m guessing you’ll need about 1/2 cup.

  • I love the use of sundried tomatoes in the recipe. I think I will try this also with basil pesto as an alternative. And because I have some on hand.Yum!

  • Have been looking for a fresh spin on a cold weather favorite! Can not wait to try!

  • This takes grilled cheese to a whole new level! We used fresh mozzarella and dipped in tomato soup! Loved, loved, loved it!

  • I made this grilled cheese sandwich and it was an instant hit. I would try the same with other spreads such as basil pesto and tahini sauce.

  • Made these tonight for my husband and 2 year old. I have been looking for super fast recipes on nights when I am pressed for time and this fit the bill. Could not have been easier to zip out to my garden and pick basil and throw this together in about 5 minutes. I used canola oil instead of butter and cooked on med-low. They turned out great, crispy and delicious with a perfect tang from the pesto. I served it with a green salad and Jenn’s buttermik ranch dressing. I will be using the rest of the pesto for pasta with chicken sausage later in the week.

    • This was literally the best grilled cheese I’ve ever had! I bought Gruyere cheese to cook with, even though it was a bit expensive. I also added two pickles inside the grilled cheese, and cooked tomato soup to dip the grilled cheese in! Will definitely be making again!

  • 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
    • 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?

    • 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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