Roasted Tomato Soup with Grilled Cheese

This is by far one of my favorite soups. I especially love to make it and eat it in that transitional period between summer and fall, in late August/early September when the last of the heirloom tomatoes are still lingering around. Roasting the tomatoes gives this soup its depth of flavor and umami, throwing your mouth into pure ecstasy. I’ve tried a few different recipes and prefer mine without cream. Partially because I don’t eat dairy, but also because I don’t think that this soup needs it; it is ridiculously delicious all on its own, again, due to the flavors released by the roasted tomatoes, onions, and garlic.

I did make a grilled cheese sandwich for this post because I felt that a good tomato soup is never complete without a grilled cheese. I normally would abstain, since I can’t have cheese (sadly), but I felt that this pairing had to happen for this recipe.

Without further ado,

Roasted Tomato Soup with Grilled Cheese

Ingredients for the Soup

2 lbs tomatoes (any variety, in fact I prefer a variety since their varying levels of acidity/sweetness contribute to the flavor of the soup) cut in half or quartered, depending on the size.
4 tbsp. extra virgin olive oil
1 tbsp. salt
1 tsp. freshly-ground black pepper
2 large onions, quartered
6 whole garlic cloves, peeled
1/4 tsp. crushed red pepper flakes
1/2 tsp. paprika
1 tsp. oregano
1 tsp. thyme
1 to 1 1/2 quarts vegetable stock
A healthy bunch of basil leaves, chopped

Ingredients for the Grilled Cheese

Slices of your favorite bread, however many you are serving. I would recommend a hearty bread.
Slices of your favorite cheese, like cheddar, manchego, provolone, or mozzarella.
A drizzle of extra virgin olive oil

Directions for the Soup

  • Preheat the oven to 375 degrees F. In a large bowl, toss together the tomatoes, onions, garlic, extra virgin olive oil, salt, and pepper. Spread the vegetables on a baking sheet lined with foil and roast for about 30-45 minutes, until they are well browned and squishy-looking.
  • Check on them after the 30-minute mark. All ovens are different. When the vegetables finish roasting, transfer them with all of the juices on the sheet to an 7-quart crock pot/dutch oven. I love my Le Creuset Round Dutch Oven. Add the paprika, oregano, thyme and vegetable stock, taste for salt and pepper. Depending on the consistency you’re trying to achieve, add less or more stock. Bring to a boil and simmer uncovered for 40 minutes. The soup will reduce and thicken.
  • After the soup has been reduced, take it out of the dutch oven and transfer to a blender. Puree until you achieve a smooth consistency. If you like your soup to have more texture, do not puree it, but pulse a few times until you have a chunky consistency. It’s best to do this in batches.
  • Put it back into the dutch oven, taste for seasonings one more time, simmer for another 5-10 minutes. Serve immediately, topped with chopped basil and the grilled cheese.

Directions for the Grilled Cheese

  • I recommend starting the grilled cheese when your soup is simmering for the last 5 minutes of cooking.
  • Heat up a medium-sized pan over medium-high heat. Add a drizzle of olive oil to coat the pan and add the bread slices. Turn the heat down to medium-low. Toast on one side until a rich golden brown, flip, top with the cheese and cover with the toasted side down. Toast until all sides are golden brown and the cheese is melty and gooey. Serve immediately with the soup.
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