Grilled Cheese with Tomato & Basil

This grilled cheese with tomato is one of the best grilled cheese recipes out there, featuring roasted tomatoes, tomato mayo, basil, and melty mozzarella.

Grilled cheese with tomato | Best grilled cheese

I was reading a book for work and came across this quote by Michael D. Krause: “The only thing that stands between a person and what they want in life is the will to try it and the faith to believe it is possible.” For Alex and me, that goal was to learn to cook. We started with little more than the will to try. At the beginning, I couldn’t even boil a pot of water for pasta. But over the years we learned, little by little, to have the faith to believe it was possible. Keep reading for how this best grilled cheese sandwich (aka grilled cheese with tomato and basil), was inspired by not knowing anything in the kitchen.

Related: 10 Amazing Vegetarian Sandwiches

Grilled cheese with tomato | Best grilled cheese | Roasted tomatoes

The inspiration: grilled cheese with tomatoes

People ask us how to get started cooking. Some of our best advice is: just try it. Believe that it is possible. Don’t expect yourself to be perfect first time. Give yourself grace. Try and try again. Take risks and gain the rewards, or learn from the failure. Be enthusiastic, and let your enthusiasm grow into passion. Start where you can, and take baby steps from there. Work within your means. It sounds really generic, but this is about 90% of what we know about cooking.

This grilled cheese with tomatoes recipe is one of those baby step recipes, because it’s “just grilled cheese”. But then again it’s not “just grilled cheese” because it’s one of the best grilled cheese recipes we know of. It’s a recipe that’s great for the beginning cook: it’s easy, but also a bit elevated since it involves roasting tomatoes and using fresh herbs.

Related: Summer Dinner Recipes to Eat Al Fresco | Italian Pizza with Pesto

Grilled cheese with tomato | Best grilled cheese | Sliced bread

How to make grilled cheese with tomatoes & basil

This grilled cheese with tomatoes & basil isn’t just any old grilled cheese. And it’s also a little more elevated than simply tucking tomatoes and basil into a grilled cheese recipe (which is also delicious, mind you). For this one, cherry tomatoes are roasted just long enough until they’re starting to burst. Then you’ll take them out of the oven and mash them to extract the juice. You’ll use that juice from the roasted tomatoes to mix in with a bit of mayo for a killer sauce. It becomes a sort of roasted tomato mayonnaise and totally makes the sandwich! Then of course, you’ll add to that the peppery bite of fresh basil.

The combination of the savory tomatoes, silky mayonnaise and fresh basil on crunchy grilled bread is a little bit of heaven. And it just might inspire you to more beautiful things you can create in the kitchen. If you try it, let us know in the comments below!

Related: Best Basil Recipes | Best Fresh Tomato Recipes

Looking for vegetarian sandwich recipes?

Outside of this best grilled cheese with tomato & basil, here are some other vegetarian sandwiches we love:

This recipe is…

This grilled cheese with tomato & basil is vegetarian. For gluten-free, use gluten-free bread.

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Grilled Cheese with Tomato & Basil

1 Star2 Stars3 Stars4 Stars5 Stars (8 votes, average: 4.63 out of 5)

  • Author: a Couple Cooks
  • Prep Time: 10 minutes
  • Cook Time: 20 minutes
  • Total Time: 30 minutes
  • Yield: 4 1x


This grilled cheese with tomato is one of the best grilled cheese recipes out there, featuring roasted tomatoes, tomato mayo, basil, and melty mozzarella.


  • 2 pints (4 cups) cherry tomatoes
  • 1/4 cup mayonnaise
  • 2 cups shredded mozzarella cheese
  • 8 basil leaves
  • 8 slices bread
  • Butter
  • Kosher salt


  1. Preheat the oven to 400°F.
  2. Line a baking sheet with parchment paper and place the tomatoes on the sheet. Roast for 15 minutes until the tomatoes are starting to burst.
  3. Place the tomatoes in a bowl and carefully mash with a potato masher to extract the juice. Strain the tomatoes completely and reserve the juice in a small bowl. Mix 1 tablespoon of the juice into ¼ cup mayonnaise until it has the consistency of a sauce (double the tomato juice and mayonnaise for extra sauce). Reserve the strained tomatoes and sprinkle them with kosher salt.
  4. Spread each slice of bread with tomato mayo. Top with 1/4 of the strained tomatoes, shredded mozzarella, and some torn pieces of basil. Sprinkle the toppings with a pinch of kosher salt and top with another slice of bread.
  5. Heat a grill pan to medium high and brush it with butter. Cook the sandwiches until toasty and the cheese is melted, about 3 minutes per side. Serve immediately.
  • Category: Main Dish
  • Method: Stovetop
  • Cuisine: American

Keywords: Grilled Cheese Recipe, Grilled cheese with tomato, Best grilled cheese, Tomato Basil, Tomato Basil Grilled Cheese,

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About the Authors

Sonja Overhiser

Cookbook Author and writer

Sonja Overhiser is author of Pretty Simple Cooking, named one of the best healthy cookbooks of 2018. She’s host of the food podcast Small Bites and founder of the food blog A Couple Cooks. Featured from the TODAY Show to Bon Appetit, Sonja seeks to inspire adventurous eating to make the world a better place one bite at a time.

Alex Overhiser

Cookbook Author and photographer

Alex Overhiser is an acclaimed food photographer and author based in Indianapolis. He’s host of the food podcast Small Bites and founder of the recipe website A Couple Cooks. Featured from the TODAY Show to Bon Appetit, Alex is author of Pretty Simple Cooking, named one of the best vegetarian cookbooks by Epicurious.


  • Reply
    Ordinary Blogger (Rivki Locker)
    September 1, 2014 at 3:17 pm

    What a lovely recipe. I never think of roasting tomatoes but it really brings out the sweetness. You’re so right about just trying it. When I got married I didn’t know how to cook anything but macaroni. A few cookbooks and pork later I was well on my way.

  • Reply
    Tina Muir
    September 1, 2014 at 4:24 pm

    Oh my, this looks amazing! PLEASE add this to my meatless monday recipe, people need to see this recipe! My other half LOVES grilled cheese, and this is just one step (if not more) even better :)

  • Reply
    Liz @ Floating Kitchen
    September 1, 2014 at 4:29 pm

    Dang this looks so good! Beginners and experts will love this. Can never have enough grilled cheese in my life!

  • Reply
    Chrystin @ A Mate & a Rottweiler
    September 1, 2014 at 6:08 pm

    What a simple & delicious sandwich! The photo is beautiful and I love the quote you posted at the beginning—it’s the perfect quote for my husband & I at this point in our lives where we are transitioning and starting a new adventure! :-)

    Kisses from Buenos Aires xx

  • Reply
    September 1, 2014 at 11:35 pm

    This is just too delicious! :)

  • Reply
    jenna @ just j.faye
    September 2, 2014 at 9:04 am

    You can never go wrong with grilled cheese! I love the addition of basil.

  • Reply
    Amy @ Parsley In My Teeth
    September 2, 2014 at 10:46 am

    Great advice! That’s certainly how I started out as well. And I think anyone who gives this gorgeous sandwich a try will be hooked for life!

  • Reply
    September 2, 2014 at 10:50 am

    YUM!!!!!!! I’m definitely going to try this sandwich.

    So glad you guys persisted with cooking. I can still remember learning to cook, even though it was more than 50 years ago. It was definitely trial and error, because my mother would not take the time to teach me to cook. However, if I was quiet, I could watch her, and that really paid off when it came to certain techniques (like making dumpling noodles), because I absorbed the technique from watching so it wasn’t too hard when I actually went to make them.

  • Reply
    Katie @ Whole Nourishment
    September 2, 2014 at 11:06 am

    Love the quote, your advice, and this recipe. I don’t make grilled cheese enough and this is a good reminder I should!

  • Reply
    September 2, 2014 at 12:05 pm

    “Give yourself grace” – I love that. It’s definitely something I need to get better at. I’m another one who is so glad that you continued cooking and you continue to share your recipes with us; this is pretty much the sandwich of my dreams.

  • Reply
    Natalie @ Paper & Birch
    September 2, 2014 at 1:08 pm

    This looks perfect for this rainy day we’re having!

  • Reply
    Laura (Blogging Over Thyme)
    September 2, 2014 at 2:23 pm

    Ohhhh! This grilled cheese looks glorious! Practically drooling on my keyboard as I type this.

  • Reply
    molly yeh
    September 2, 2014 at 3:12 pm

    this is a damn pretty grilled cheese.

  • Reply
    September 2, 2014 at 4:52 pm

    This looks absolutely delicious. I love roasted tomatoes and I have a grill pan! Making this, this week.

  • Reply
    Katrina @ Warm Vanilla Sugar
    September 2, 2014 at 7:38 pm

    Roasted tomatoes taste like candy! Love this idea!

  • Reply
    September 3, 2014 at 8:32 am

    These look and sound great. I love that the tomatoes are grilled. Like a Caprese salad sandwich!

  • Reply
    September 3, 2014 at 9:49 am

    You have just made my new favourite sandwich. I couldn’t think of something I want more right now… and I’m in bed writing this having just cleaning my teeth… mmm :)

  • Reply
    Nicole B.
    September 3, 2014 at 10:37 pm

    Just yesterday I was thinking how I wanted to find a recipe for grilled cheese with an extra delicious twist and this looks amazing! Thanks for sharing!

  • Reply
    September 5, 2014 at 11:57 am

    This sandwich looks EPIC! I cannot get enough roasted cherry tomatoes this time of year.

  • Reply
    Millie | Add A Little
    September 7, 2014 at 2:38 am

    I love roasting tomatoes! brings out the gorgeous sweetness!

  • Reply
    September 8, 2014 at 9:08 am

    Gorgeous! This looks super tasty. :)

  • Reply
    September 15, 2014 at 5:43 am

    Yep. Sold, this is my ideal sandwich.

  • Reply
    Phoebe Lapine
    September 22, 2014 at 5:24 am

    This looks easy and delicious! Love the idea of a Caprese salad grilled cheese.

  • Reply
    January 20, 2015 at 10:34 am

    This was the first of your recipes that I tried and it was to die for.. I loved it! I added in a little bit of pesto and I also used buffalo mozzarella since it has a little more “kick” than just plain old mozzarella. I regreted not stocking up on the mozzarella – would have loved having this again for lunch today

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