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Roasted Garlic Caprese Grilled Cheese. Slow roasted summer tomatoes and sweet roasted garlic, sandwiched between slices of sourdough bread with fresh basil pesto and mozzarella cheese. Then pan-fried until the cheese is melty and the bread is crisp. Tis’ a true end-of-summer delight. 

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com

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Is there anything better than a really good grilled cheese? To me, it’s just feel-good classic comfort food. As a kid, my grilled cheese sandwiches consisted of whatever bread we had laying around the kitchen, cheese, and butter. My dad kept it simple, but they’d never disappoint. 

It’s truly hard to beat a melted cheddar sandwiched between 2 slices of buttered bread. 

However, as much as I love the classic simple grilled cheese, I’m also all about making grilled cheese the “fancy” way. Though I don’t really consider this recipe fancy – just totally delicious. 

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com

Here are the details

Aside from the time needed to roast the tomatoes, this is almost as easy as the 3-ingredient grilled cheese my dad would make. Almost. 

First things first, the tomatoes. Find some really good ones with really nice color. Mine were on their last leg, which was honestly perfect for roasting. 

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com

Then grab a head of garlic and smash it down. Toss the cloves onto a baking sheet with the tomato slices and season everything generously with salt and pepper. Next, roast away until the tomatoes start to char and become even sweeter than before. 

At the same time, the garlic roasts and turns into a buttery golden clove that can easily be smashed further down into a paste. 

When the tomatoes are finished, I further mash the cloves of garlic. Then I mix the tomatoes and garlic with basil pesto. 

Now all that’s left to do is assemble. 

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com

My secret 

Fig preserves, which are certainly not traditional in a Caprese. But the jam adds a sweetness that really balances out the richness of the melted cheese and the savory flavors from the basil. 

It’s the layers of flavor that really make this Caprese grilled cheese stand out.

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com

Layer the jam with mozzarella cheese, roasted tomato slices, garlic pesto, and then more cheese. Pan-fry the sandwiches with butter until golden and crisp. The cheese on the inside becomes that melty goodness we love so much. 

Five minutes later you’ll have the best summery grilled cheese, so so delicious! A wonderful way to use up the end-of-summer tomatoes and herbs and celebrate these precious last few weeks of summer. 

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com

Looking for other grilled cheese recipes? Here are a few ideas: 

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese

Everything Cheddar Tomato Bacon Grilled Cheese

French Onion and Apple Grilled Cheese

Breakfast Grilled Cheese

Lastly, if you make this, Roasted Garlic Caprese Grilled Cheese be sure to leave a comment and/or give this recipe a rating! Above all, I love to hear from you guys and always do my best to respond to each and every comment. And of course, if you do make this recipe, don’t forget to tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!

Roasted Garlic Caprese Grilled Cheese

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com
4.93 from 57 votes
2 grilled cheese
calories 781kcal
Prep15 minutes
Cook45 minutes
Total1 hour
A wonderful way to use up garden tomatoes and herbs and celebrate these last few weeks of summer!
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Ingredients 

Instructions 

  • 1. Preheat oven to 425° F.
    2. Arrange the tomato slices on a parchment-lined baking sheet. Scatter the smashed garlic cloves around the tomatoes. Drizzle everything with olive oil and season with salt pepper, and chili flakes. Bake 20-25 minutes, until tomatoes are deeply roasted.
    3. Remove the garlic from the pan and pop the cloves out of the skin. Mash the cloves with a fork into a paste. Mix the roasted garlic with the basil pesto.
    4. Brush the outside of each slice of bread with butter. On the inside of half of the slices of bread, spread with fig preserves. Evenly layer the cheeses, the tomatoes, pesto, and the remaining cheese. Add the top piece of bread.
    5. Melt 1-2 tablespoons butter in a large skillet over medium heat. Place the sandwiches in the skillet and cook until golden on each side, about 3-5 minutes per side. EAT and ENJOY!

Nutrition

Calories: 781kcal

Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.

Did you make this recipe? Please rate & comment below.

Roasted Garlic Caprese Grilled Cheese | halfbakedharvest.com

Meet Tieghan Gerard

I'm Tieghan, the recipes you'll find here are inspired by the people and places I love most. I try to live simply, eat seasonally, and cook with whole foods. My hope is to inspire a love for amazing food, as well as the courage to try something new!

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4.93 from 57 votes (20 ratings without comment)

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118 Comments

  1. Mary Taylor says:

    Sounds wonderful

    1. Tieghan Gerard says:

      Thanks so much, Mary!

  2. Melanie says:

    Very perplexed as to when I add the basil? Is it made into a pesto first? Seems I’m not the only one confused. Instructions and ingredients don’t match.

    1. Tieghan Gerard says:

      Hi Melanie,
      So sorry for any confusion! You can add the fresh basil into the sandwich in step 4. I hope you love this recipe!

  3. Elyse says:

    5 stars
    Absolutely loved this flavor!!! Ours was falling apart while we were eating it. Some parts felt soggy. What would you recommend to do to fix that??

    1. Tieghan Gerard says:

      Hey Elyse,
      Thanks so much for making this recipe!! I might go a little lighter on the fillings next time:) I hope this helps!

  4. Helen says:

    3 stars
    I don’t normally like cooked tomatoes on sandwiches, but these were delicious roasted with the garlic, although Heirloom tomatoes are gigantic and we needed only one, if even that. However, neither of us liked the flavor combination of pesto and fig preserves, which I realize was optional (the preserves), but just very unappealing. If we ever make it again, I’d definitely leave them out.

    1. Tieghan says:

      Hi Helen,
      Thanks so much for trying this recipe and sharing your feedback! So sorry you didn’t love the flavor combos, let me know if you try again without the fig jam! xT

  5. Jas says:

    Hi! Just wondering when you add the basil leaves – before or after the pan?

    1. Tieghan says:

      Hey Jas,
      You will add the basil leaves with the tomatoes in step 4. I hope you love this recipe! xT

  6. Joey R says:

    5 stars
    WOW!!!! So good best grilled cheese we’ve had. And I’ve had a lot of grilled cheeses

    1. Tieghan says:

      Lol thanks so much Joey!! Love to hear that this recipe was such a winner! Thanks for making it! xT

  7. Nia says:

    5 stars
    Perfect Sunday evening dinner! I couldn’t find fig preserves in my small supermarket in the UK, but did find a fig & balsamic chutney which I subbed. It really added a nice bit of sweetness to the rest of the ingredients. Delicious!

    1. Tieghan says:

      Thanks so much for trying out the recipe! 🙂 xT

  8. Linda says:

    The instructions aren’t clear. What do you do with the basil leaves?

  9. marian says:

    So I’m assuming the one cup basil, parmesan and garlic is made into a pesto first?