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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 |

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 |

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 |

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 |

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 |

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 |

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

Prep Time 15 minutes
Cook Time 45 minutes
Total Time 1 hour
Servings: 2 grilled cheese
Calories Per Serving: 781 kcal

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



  • 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!
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    1. Thanks Jaimie!! You will add a little bit with the tomatoes and cheese so the basil is layered on each sandwich. I hope you love the recipe! xT

  1. 5 stars
    I rarely get Saturdays off, but when I do, I go to the local farmers market. I saw this recipe the other day and couldn’t wait for the weekend! This morning, I picked up bread, garlic, tomatoes, basil, and pesto. I made it for lunch!

    This sandwich is delicious and I can’t wait to make it again!

  2. My husband and I made this tonight and this is one of the best things we’ve eaten in a long time! The fig preserves added such a nice, sweet balance to the pesto that I don’t think I’d do without it! This is a keeper recipe for sure!!

    1. Hey Chelsi,
      Awesome!! I am so glad to hear that this recipe was a winner, thanks for making it! Hope you’re off to a great Saturday! xT

    1. Hi Amy,
      Thanks so much for making this recipe, I love to hear that it was enjoyed! Honey would also work well in place of the fig preserves. Please let me know if you have any other questions! xx

  3. 5 stars
    This is possibly one of the most amazing things I’ve ever eaten!! The roasted garlic was next level on the grilled cheese and I didn’t even mix it in with the pesto.
    Thank you so much for making these delicious recipes! I have yet to make something that I didn’t like.

    1. Hi Liz,
      Happy Friday!! Thanks a lot for trying this recipe out, I am so glad to hear it was enjoyed! Have a great weekend:)

    1. Hi Jan,
      Happy Friday!! Thanks a lot for trying this recipe out, I am so glad to hear it was enjoyed! Honey is great to use in place of fig preserves. Have a great weekend:)

    1. Hey Alyssa,
      Amazing!! I love to hear that this recipe was tasty, thanks so much for making it and sharing your review:) xTieghan

  4. So delicious! I used an onion jam on one of the sandwiches for a more savory flavor – good, but recommend fig preserves more.

    Also, had to do one sandwich at a time. First one was perfectly browned, then I burned the other 2…do I need to let the pan cool between sandwiches?

    1. Hi Stephanie,
      I am so glad this recipe was enjoyed, thanks for making it! Sorry to hear your second sandwiches burned. I would say to turn the heat down between sandwiches since the pan is already hot. I hope this helps for next time! xTieghan

  5. 5 stars
    Made these last night and my only regret was that I didn’t think to double the recipe ahead of time! These were SO good. SO full of flavor and easy to make. I have also apparently been not living at I’ve never roasted and then smashed full garlic cloves before…. Oh my goodness, is there a better smell or flavor in the world!? Make these. You won’t regret it!!

    1. Hey Ali,
      Happy Wednesday! I love to hear that this recipe was tasty, thanks for making it! Thanks for your kind message? xxT

  6. 5 stars
    The roasted garlic capers grilled cheese sandwiches were delicious. This recipe is a keeper. Thank you.

  7. 5 stars
    I made this last night but used brie instead because it’s all I had. Fig and brie just make sense. So so good and pretty simple. I will definitely be making again.

    1. Hi Jenelle,
      Happy Tuesday!! Thanks a bunch for trying this recipe and sharing your feedback! I am so glad it was enjoyed:)

  8. 5 stars
    Made this for dinner last night – super yummy! My husband said this is definitely a keeper recipe. I did not add the fresh basil leaves (not in the recipe) and honestly, because of the basil pesto – didn’t miss them. I’m not already imaging these with a nice tomato soup this fall / winter!

    1. Hi Dee,
      Happy Tuesday!! Thanks a bunch for trying this recipe and sharing your feedback! I am so glad it was enjoyed:)

  9. The recipe sounds delicious.

    Ingredients call for 1C. Basil leaves. But they’re not mentioned in the instructions. Where/how are they meant to be used?

    1. I noticed that too. This seems to happen a lot with her recipes. Maybe we can scatter them on the hot tomato/garlic out of the oven to wilt them? If so I would not use pesto…..

      1. Hi Candace,
        You can layer in step 4 with the cheese and tomatoes:) Please let me know if you have any other questions! xx

    2. On her instagram video she layered the basil leaves between the cheese and tomatoes when assembling the sandwich! Separate from the pesto.

    3. Hi Stacy,
      Thanks so much! You can layer the fresh basil after the cheese. I hope you love the recipe, please let me know if you give it a try! xTieghan