Grilled Cheese and Tomato Soup is classic COMFORT FOOD! Fresh ingredients maximize flavor and the mini grilled cheese sandwiches are the cutest ever!
Grilled Cheese and Tomato Soup
Tomato soup for me, growing up was of the tinned variety. Salty with just a little sweetness from the tomatoes but so comforting. We would toast some bread, slather it in butter then dip it in the soup. Although I’m not a fan of soggy bread and that piece of toast moved at lighting speed from the soup to my mouth so I could devour it while still crunchy.
This Roasted Tomato Soup is all that, on steroids. Mini grilled cheese and tomato soup totally homemade with sun-dried tomato pesto is classic comfort food made better! Kids and adults alike will LOVE dipping the mini grilled cheese in the tomato soup!
Homemade Tomato Soup Recipe Tips
- Plump, ripe roma tomatoes and a few little sweet cherry tomatoes are roasted until they get a little caramelized and release their juices. Roasting the tomatoes intensifies their flavor but also adds some sweetness.
- Onion and garlic are roasted together with the tomatoes until soft and sweetened. If you haven’t tried roasting garlic, you really must. It mellows out the flavor but also makes it incredibly sweet and creamy.
- Sundried Tomato Pesto adds a real punch of flavour to this tomato soup. You can feel free to use store bought pesto or try your hand at making your own using this Easy Sundried Tomato Pesto recipe (spoiler alert – it takes just minutes)
To finish off, it all goes into a blender with the pan juices and some broth, then blended until as smooth as you like it. Cook it a little longer in a saucepan with some salt, pepper and dried herbs and you’re done.
Mini Grilled Cheese Recipe Tips
These Mini Grilled Cheese sandwiches are everything a classic grilled cheese should be. Full of flavor, but simple, warm and oozy. I use two cheeses in these to get a wonderful combination of flavor and melt. Just a little salt and pepper on the inside, the the outside is brushed with melted butter. That’s all you need but just make sure to choose a good full fat cheese, cheddar is best, and some mozzarella. This is the perfect grilled cheese and tomato soup combo! You’ll love serving this for a comforting lunch, weekday supper, or even gathering everyone around the table for a casual Sunday Supper.
Grill these grilled cheese sandwiches on a griddle while weighted down. I weigh them down for two reasons
- It keeps more heat around the little sandwiches helping to melt the cheese before the bread burns
- It helps to ensure you get those defined griddle marks that just look really cool
These are great for little hands too!
If you have a hankering for more grilled cheese, recipes check out Our BEST Grilled Cheese and Soup Pairings!
Now, can you just imagine dipping that amazing mini grilled cheese into a rich roasted tomato soup? The smell that fills the house is so satisfying and then devouring it on a cool afternoon or evening takes me right back to those fond childhood memories.
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Grilled Cheese and Tomato Soup
For the Roasted Tomato Soup
- 2 tablespoons olive oil
- 4.5 lbs roma tomatoes fresh ripe
- 3 red onions
- 8 cloves garlic whole
- 1.5 cups cherry tomatoes cut in half
- 1.25 L vegetable broth or chicken broth
- 1 cup sundried tomato pesto
- 2 teaspoons dried oregano
- 2 teaspoons dried parsley
- Salt and pepper to taste
- handful basil leaves
For the Mini Grilled Cheese
- 1 stick French bread
- 12 slices cheddar
- 12 slices mozzarella
- 3 tablespoons butter melted
- Salt and pepper to taste
For the soup
- Preheat the oven to 200C / 400F / 180C fan forced. Line 2 large baking trays with foil and drizzle over half of the oil.
- Cut the roma tomatoes in half and remove the core section at the top of each half. Peel the onions and chop them in half. Place the tomatoes and onions, cut side up in the baking trays then scatter the unpeeled garlic cloves among them. Drizzle over the remaining oil and sprinkle with salt.
- Bake for 50 minutes. Cut the cherry tomatoes in half and add them to one of the baking trays for the last 10 minutes. Remove everything from the oven as soon as the cherry tomatoes are just starting to blister.
- Transfer a few of the cherry tomatoes to a plate and set aside (these will be used for garnish)
- Squeeze the roasted garlic out of the skins. Discard the skins, then add the garlic, tomatoes, onions, the juice from the baking trays, pesto and stock to a blender (you may need to do this in 2 batches).
- Blend to the consistency you like. Then pour the soup into a large saucepan. Add the oregano, parsley, and salt and pepper to taste then heat for 5 minutes.
For the mini grilled cheese
- Cut 24 thinnish slices from the bread stick. Sit some cheddar and mozzarella on top of 12 slices (don’t be shy, make sure to cover the bread with the cheese). Sprinkle with a little salt and pepper, then top with the remaining slices of bread
- While the grill is heating over medium heat, brush both sides of the mini sandwiches with melted butter.
- Sit the sandwiches in a single layer on top of your grill, then place a large baking tray on top and weigh them down with some plates. Let them grill for 5 minutes on one side, then turn them over and grill them for 5 minutes on the other until they’re golden on the outside and the cheese has melted
- Pour the soup into serving bowls, and top with the remaining cherry tomatoes and some basil. Serve with the mini grilled cheese on the side.