One of the most comforting and nostalgic childhood favourites is a grilled cheese sandwich paired with tomato soup. Nobody wants to eat soup in the summer, so my Tomato Grilled Cheese Sandwich is perfect! Summer fresh tomatoes and basil pesto are tucked into the sandwich to make the ultimate flavour combination!
Full disclosure time – I’m not a fan of grilled cheese sandwiches at all. In fact, I think they’re gross. At least that was my mindset before I learned that not all of them are created equally. My Tomato Grilled Cheese Sandwich just might change your mind too if you are once like I was!
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Both John.e and McKenna love grilled cheese sandwiches and tomato soup. I make it for them both often during the winter months. And, they both have no problem with canned tomato soup, so I go for it! It’s an easy dinner and I don’t have to spend much time preparing it. Sometimes, I’ll go the extra mile and make homemade tomato soup, but in most cases, they just want the canned stuff.
I’m all about the flavours of homemade soup and a really good grilled cheese sandwich, but if they want the canned stuff from the store, it’s less work for me! To really kick things up, I highly suggest you consider adding sliced tomatoes to your grilled cheese along with a smearing of basil pesto. It’s so good! I didn’t even have tomato soup with mine!
INGREDIENTS NEEDED TO PREPARE THIS RECIPE
Here is a list of the ingredients you will need to prepare this recipe. For exact amounts and measurements, refer to the printable recipe card located near the bottom of this post.
- Bread – You can use any bread you like, but sturdier bread like sourdough works best.
- Tomatoes – Use locally grown tomatoes if possible. It really does make a world of difference!
- Mayonnaise – This is one of my secrets. I don’t use butter on grilled cheese; I use mayo instead!
- Ground Black Pepper – I like a larger grind, and fresh ground is best.
- Basil Pesto – You can make your own pesto at home or you can use the store-bought type. I mentioned that I’m not a huge fan of basil pesto, but whenever I buy it, this is the only brand I get.
- Cheese – I used aged white cheddar, but you can use any good melting cheese. Also, you can use sliced cheese or shredded cheese here.
A few years ago, I shared my recipe for Peppery Double Parmesan Basil Pesto with you. Back then, John.e was still working as a graphic designer. A colleague of his – Adam – grew a large amount of basil on his deck right in the city. He gave a bunch to us. The leaves were so tender and fresh, and they had a very consistent green colour. I grow my own basil now and I find it to be quite finicky! But, this basil was perfect!
I used Adam’s basil in one of the best ways I know how – uncooked! I think a herb as delicate as basil, doesn’t need anything but a good wash in some cold water. That’s why pesto is my go-to dish for fresh basil. It’s pureed with some other ingredients, never losing its beautiful green colour, flavour, or scent. In my basil pesto recipe, I did just what the title of the recipe suggests – I increased the amount of ground black pepper and the amount of parmesan too.
I also added some dried red chili flakes. The ground black pepper provides heat and warmth, while the dried red chili flakes provide heat and spice. I balanced that heat with the saltiness and creaminess of the parmesan, as well as a little bit of lemon juice. Delicious! It’s the only basil pesto recipe I ever use!
HOW TO MAKE A TOMATO GRILLED CHEESE SANDWICH
Spread one slice of bread with half of the mayonnaise and place it, mayonnaise side down, in your skillet. Smear that same slice with the basil pesto. Layer on half of the cheese and top the cheese with sliced tomatoes. At this point, season the tomatoes with ground black pepper. Next, add the remaining cheese and finally, the remaining slice of bread. Smear the top of that last slice of bread with the remaining mayonnaise.
Over medium heat, toast the sandwich for 3-4 minutes. Flip the sandwich over and toast for another 3-4 minutes.
Remove the sandwich from the skillet and transfer to a cutting board. Slice and serve with kettle chips.
Lord Byron’s Notes
Flipping a grilled cheese – especially one with tomatoes in the center! – can be challenging. To avoid any mishaps, you can lift the sandwich completely out of the skillet and place it onto a dinner plate. Place a second dinner plate on top and with one hand on the bottom and one hand on top, in one quick movement, flip the plates. Set aside the top plate and slide the sandwich back into the skillet, toasted side up. Easy peasy!
SUMMER FRESH TOMATOES
If you’re thinking about making a Tomato Grilled Cheese Sandwich, you must have some summer fresh tomatoes on hand, right? The whole concept of a simple recipe like this is about combining fresh tomatoes with a few basic ingredients. I have used both roma and beefsteak tomatoes, however, any tomato will do, but I think the best tomatoes are the ones with more meatiness.
When a tomato is described as being meatier, it simply means that the ratio of tomato flesh to the seeds and pulp mixture is higher. A good example of this is the beefsteak tomato. They are quite large and the walls of the tomato are thick and sturdy. They’re most often found on sandwiches for this reason.
In terms of taste, I prefer the roma tomato. In my opinion, this variety has the best flavour, and most certainly, the best colour. A perfectly ripe roma tomato has a deep red colour and just pops in contrast to other recipe ingredients. I use the roma tomato almost exclusively in my recipes. Tomatoes on the vine are perfect for this recipe too! This year my romas didn’t grow well at all, so I had to pair them with heirloom tomatoes.
HOW TO SERVE A SANDWICH
I dearly love sandwiches; I really do! I’m that one person who loves to bake and cook, but can be easily satisfied with a sandwich. In fact, before I started to work from home, a few times a week, I would bring a sandwich to work for lunch. My favourite quick lunch is ham and cheese on good grainy bread with a hot cup of coffee. I love sandwiches with hot coffee!
But, on the occasion that I make sandwiches for dinner, I go all out. I love to serve sandwiches with kettle chips and a pickle on the side. Sometimes, I serve them with coleslaw and potato salad. A good, well-made sandwich can be quite impressive. Look at my White Bean Salad Sandwich and my Smashed Lentil Salad Sandwich. I would totally serve one of these to any guest! Wouldn’t you?
Do You Like This Recipe?
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Tomato Grilled Cheese Sandwich
- 2 slices sourdough bread
- 2 tablespoons mayonnaise
- 2 tablespoons basil pesto
- 1 sliced tomato, roma or heirloom
- 1/4 teaspoon ground black pepper
- 1 cup shredded aged cheddar cheese
- Spread one slice of bread with half of the mayonnaise and place it, mayonnaise side down, in your skillet.
- Smear that same slice with the basil pesto.
- Layer on half of the cheese and top the cheese with sliced tomatoes. At this point, season the tomatoes with ground black pepper.
- Next, add the remaining cheese and finally, the remaining slice of bread.
- Smear the top of that last slice of bread with the remaining mayonnaise.
- Over medium heat, toast the sandwich for 3-4 minutes.
- Flip the sandwich over and toast for another 3-4 minutes.
- Remove the sandwich from the skillet and transfer to a cutting board. Slice and serve with kettle chips.
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