🍽️

Roasted Tomato Soup with Grilled Cheese Sandwich

Course
Dinner
Servings

4

Tips & Tricks:

  • 🔪 Skip steps with knife if you completed Prep Day!
  • 🔪 Soup can be made ahead 5 days refrigerated and up to 3 months if frozen.
  • ❌ Use gluten free bread for GF grilled cheese sandwiches.
  • 🧄 Definitely consider roasting several heads of garlic. Squeeze the roasted garlic onto a plate and spread out so they aren’t touching, place the plate in the freezer for about an hour, then place frozen garlic into a plastic baggie for storage in the freezer. Can be frozen for up to 3 months. Thaw individual cloves when needed.
  • For the grilled cheese, I like to use mayonnaise in place of butter! Gets super crispy and the flavor is *chefs kiss*

Ingredients:

  • Soup:
    • 3 pounds roma tomatoes, cut in half
    • 1 head of garlic
    • 3 tablespoons olive oil
    • Freshly ground salt and pepper
  • Caramelized onions:
    • ½ tablespoon olive oil
    • 2 yellow onions, thinly sliced
  • Additions to the soup:
    • ½ cup packed basil leaves
    • ½ teaspoon dried oregano
    • 1-2 cups water or vegetable broth, depending on how thick you want the soup
    • Freshly ground salt and pepper, to taste
    • 2 tablespoon of butter
  • Soup garnish:
    • 2 oz parmesan, finely grated
  • Grilled Cheese
    • 8 slices of bread, such as Texas toast, sourdough, or white bread
    • 4 Tbsp unsalted butter, softened or mayonnaise
    • 12 slices of cheese, such as cheddar, gouda, and/or Havarti

Directions:

  1. 🔪 Soup Prep - Tomatoes & Garlic
    1. Preheat oven to 400 degrees F.
    2. Cut the garlic head top off. Place the bottom half (cut side up) in a piece of tin-foil (large enough to wrap the garlic) and drizzle with olive oil and sprinkle with salt. Wrap the garlic so it is completely closed in the tinfoil.
    3. Line a large baking sheet with tin foil for easy cleanup.
    4. Place halved tomatoes (skin side up) and wrapped garlic on the baking sheet and drizzle tomatoes with 3 tablespoons of olive oil. Generously season the tomatoes with salt and pepper.
    5. Roast in the oven for 40-45 minutes, or until tomatoes are fully browned. The garlic should be roasted in the same amount of time.
    6. Once tomatoes and garlic are done roasting, allow them to cool for 10 minutes.
    7. While they are cooling I prefer to remove the tomato skins using a paper towel (just lightly pinch the skins off), but that's optional.
  2. 🔪 Soup Prep Onions
    1. While the tomatoes are roasting, you can make the caramelized onions.
    2. Add 1/2 tablespoon olive oil to a large pot or dutch oven and place over medium heat.
    3. Add the onion slices and stir to coat the onions with olive oil.
    4. Cook, stirring occasionally, and adjust the heat if they start to brown too much.
    5. Check onions every 5-10 minutes until they have completely caramelized and turned golden in color. This usually takes 30 minutes.
  3. 🔪 Soup
    1. Add tomatoes, garlic, and basil to the pot with the caramelized onions (the garlic should just squeeze out of the skins).
    2. Blend using an immersion blender until smooth. Alternatively, you can add all of these ingredients to a blender and blend until smooth. You may have to do this in batches depending on the size of your blender.
    3. After blending, transfer back to the large pot (if it's not already in there), turn to medium low heat and add in dried oregano, 1 cup of vegetable broth or water and salt and pepper to taste.
    4. Allow tomato soup to simmer for 10 minutes, adding more vegetable broth or water depending on how thick you want your soup.
    5. If freezing: Let the soup cool for about an hour on the counter. Place in freezer friendly containers (I use these), and refrigerate overnight to fully cool. Wipe away any condensation on the cover, and freeze for up to 3 months.
  4. Grilled Cheese (2 at a time)
    1. Spread 1/2 Tbsp of butter (or mayonnaise) on one side of 4 slices of bread.
    2. Set a large skillet over medium heat and place 2 slices of bread in the skillet with the butter-side-down.
    3. Stack 3 slices of cheese on the bread then the 2nd slice of bread, butter side up.
    4. Once the bottoms are golden brown, flip and brown the other sides.
    5. Once the other side is starting to brown, cover the pan for the last minute or two to get the cheese nice and melty.
  5. Serve
    1. Soup - Stir in butter and garnish with parmesan cheese.
    2. Grilled Cheese - Once you see the cheese has melted and breads are browned, remove to a plate and cut in half diagonally to serve.

Reheating Instructions

  1. Soup - Defrost in the refrigerator overnight if frozen. Reheat in a pot, simmering for about 10 minutes or until hot.
  2. No one wants reheated grilled cheese! Make this step just before serving dinner.