Grilled Cheese & Roasted Tomato Soup

Name: Grilled Cheese & Roasted Tomato Soup
Prep time: 15 min
Cook time: 45 min
Total time: 60 min
Ingredients: 8 large roma tomatoes, halved (about 2 pounds); 2 medium yellow onions, peeled and halved; a medium bulb of garlic, top removed; 1/4 cup of olive oil; salt and black pepper; 2 tablespoons of brown sugar; several sprigs of fresh thyme and oregano (or a teaspoon of dried italian herbs); 2 tablespoons of butter; 2-3 cups of stock (chicken or vegetable); 1/4 cup of heavy cream; fresh basil leaves (optional); a pinch of crushed red pepper flakes; 1/2 cup of parmesan, grated or shredded; 2 slices of your favorite bread; 2 tablespoons of mayonnaise; 2 slices of your favorite cheese; 2 ounces of your favorite shredded cheese

March 14, 2025
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When a discussion about comfort food is in full swing there is a good chance that grilled cheese and tomato soup will be mentioned.

It is a classic loved by people of all ages and whether you are sad, sick or lonely, grilled cheese and tomato soup will make you feel all better.

When making something as popular as this delicious duo, if you don’t have a family recipe in your repertoire then it will probably only take you about 30 seconds to find one online.

With a short list of common ingredients and super basic instructions, making a great grilled cheese and tomato soup doesn’t require a strict recipe, but this is what I do when I start craving those super comforting vibes.

Let’s get started…

Roasting your tomatoes, onions and garlic for the soup not only brings out their very best flavors, but it also lets the oven do all of the work. No stirring and baby sitting required.

Simply place 8 large roma tomatoes, 2 medium yellow onions and a bulb of garlic with the top sliced off into an oven safe pot, baking dish or rimmed baking sheet. Drizzle about 1/4 cup of olive oil over everything and season with 2 tablespoons of brown sugar, salt and black pepper.

Give everything a good mix and add a few sprigs of fresh thyme and oregano (or sprinkle a teaspoon of dried Italian herbs over everything).

Roast everything in a 400 degree oven until tender and slightly charred. This should take about 45 minutes, which is plenty of time to get your blender ready and make a fabulous grilled cheese…

Place a skillet over medium heat and while it is getting warm, spread a tablespoon of mayonnaise over 2 slices of your favorite kind of bread.

Place a piece of bread onto the skillet mayonnaise side down and add 2 slices of your favorite cheese and about 2 ounces of your favorite shredded cheese. I am using sliced provolone and shredded gruyere on todays grilled cheese, but so many cheeses work on a grilled cheese. American, cheddar, mozzarella, fontina… whatever you love or have in the fridge.

Place the other slice of bread mayonnaise side up over the cheese and cook the sandwich until the underside is crisp and golden brown.

Carefully flip the sandwich and cook on the other side until both sides are golden brown and the cheese is all melty and perfect.

As soon as the tomatoes, onion and garlic are tender, transfer all of the tomatoes and onion into a blender. Squeeze the roasted garlic cloves out of the bulb and add them into the blender too.

Discard the herbs and add 2 tablespoons of butter, 2 cups of broth (chicken or vegetable), 1/4 cup of heavy cream, 1/2 cup of grated parmesan, a pinch of salt and a pinch of crushed red pepper flakes and some fresh basil, if you have any on hand. Blend until smooth and add more stock if you want to thin the soup out.

If you add the ingredients right out of the oven, your soup will be nicely warm straight out of the blender, but if you waited a bit or prefer your soup piping hot then transfer it back into the pot and rewarm it on the stove for a minute.

The only thing left to do is to slice your sandwich in half and dunk it directly into your tomato soup.

No spoons necessary. Just warm, comforting, cozy vibes.

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