Did I catch your attention with Tomato Basil Soup and Grilled Cheese? This was a go-to comfort food for me as a kid and today, I’m sharing a couple secrets that kick this childhood classic into adult mode.

Roasted Tomato Soup with Grilled CheeseRoast the Ingredients

For this recipe, I roasted the tomatoes, onions and garlic. I recommend turning the oven to 425 degrees F. and roasting the onions and garlic for about 20 minutes.

At the same temp. the tomatoes will roast for 40-45 minutes. While this can be a bit of a waiting game, roasting ingredients first helps tame the acidity and enhances their flavors. I find this step to be a game changer with a lot of soup recipes.

Use a Vitamix or Immersion Blender

The best part about this soup is the velvety smooth texture. I recommend using a Vitamix or immersion blender to ensure the perfect consistency.

Roasted Tomato Soup with Grilled CheeseGive It A Day

I made my tomato basil soup a day early and let the flavors sit overnight. If you have the time, I recommend allowing the flavors to settle into themselves.

Use Three Cheeses

For the grilled cheese, you can use whatever cheeses you’d like, but I recommend choosing three for flavor variety. I used muenster, gouda and cheddar, which all melted beautifully.

Roasted Tomato Soup with Grilled CheeseGet Really Good Bread

I used a seeded sourdough bread in my recipe and I can’t emphasize enough how important it is to use really good bread for the grilled cheese.

Butter Sauce

The butter is melted with red pepper flakes and thyme and basted on the outside of the bread as you grill each side. It’s incredible. Do not skip this step.

Garnishing the Soup

Just before serving, add fresh, julienne cut basil leaves and a light drizzle of extra virgin olive oil. It makes for a very pretty presentation and is such a delicious enhancement of the basil that was blended with the soup.

You’ll have to let me know what you think!



For the Grilled Cheese

  • 4 slices of good quality bread from the bakery section of your grocery store (I used a seeded sourdough)
  • 2 slices of muenster cheese
  • 2 slices of gouda cheese
  • 2 slices of cheddar cheese
  • 2 teaspoons of Dijon mustard
  • 2 tablespoons of butter
  • 1 clove of garlic, minced
  • 1 pinch red pepper flakes
  • 1 pinch of thyme

For the Tomato Basil Soup

  • 2-1/4 lbs Roma tomatoes, halved lengthwise
  • 1-1/4 lbs cherry tomatoes, halved
  • 4-1/2 tablespoons olive oil
  • Salt and fresh ground pepper
  • 8 garlic cloves, left whole
  • 2 small yellow onions, sliced
  • 2 cups lightly packed fresh basil leaves
  • 4-6 cups vegetable broth


For the Grilled Cheese

  1. Melt your butter in a sauce pan with your garlic, red pepper flakes, and thyme.
  2. Lightly simmer, careful not to burn the garlic, while you prepare your sandwiches.
  3. Lay your slices of bread out and spread ½ teaspoon of Dijon mustard onto each slice
  4. On two of the slices of bread, add one slice of cheddar cheese, one slice of muenster cheese, and one slice of gouda cheese.
  5. Place the other slice of bread on top of the cheese. The sides with the Dijon mustard should be touching the cheese.
  6. Using a pastry brush, brush the butter onto the top and bottom of both sandwiches until all the butter is gone.
  7. Heat a grill pan over medium heat.
  8. Cook your sandwiches until both sides are golden brown and the cheese is melted.

For the Tomato Basil Soup

  1. Preheat oven to 425 degrees Fahrenheit.
  2. Place tomatoes on a rimmed baking sheet with 3 tablespoons olive oil and salt and pepper.
  3. Place onion slices and garlic cloves on a rimmed baking sheet and mix with the remaining 1 1/2 tablespoons olive oil and sprinkle with salt and pepper.
  4. Place baking sheets in the oven and roast the onion and garlic for 20 minutes.
  5. Roast the tomatoes for 40 minutes.
  6. Remove from oven and pull the peel from the tomatoes.
  7. Pour the onions, garlic and peeled tomatoes into a dutch oven pot.
  8. Add 4 cups of vegetable broth and the basil.
  9. Bring to a boil and then simmer for about 20 minutes.
  10. Add additional vegetable broth, if needed.
  11. Using a Vitamix or immersion blender, blend until smooth.
  12. Garnish with additional basil and a drizzle of olive oil, if desired.


1. You can use whatever cheeses you’d like for the grilled cheese.

2. I made the soup one day early and let it chill overnight in the fridge. The flavors were amazing the next day.

All images © Regan Baroni 2016.

  1. Kik says:

    I love your note that the flavors are even better the next day. The best kind of soups!

    • Regan says:

      Yes! This recipe is SO good. If you have the patience, next day is best for full flavor. xo

  2. […] can go wrong with tomato soup and grilled cheese? This recipe from Up Close and Tasty which includes muenster, gouda, and cheddar cheese…yes please. Her […]

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