Roasted Tomato Basil Soup with Grilled Cheese Croutons | Sip and Spice

Roasted Tomato Basil Soup with Grilled Cheese Croutons

Prep Time 20 minutes
Cook Time 1 hour 40 minutes
Total Time 2 hours
Servings 4


  • 8 Roma Tomatoes
  • 3 1/2 tablespoons olive oil
  • salt and pepper
  • 6 garlic cloves separated
  • 1 medium yellow onion diced
  • 1 28 oz. can plum tomatoes
  • 2 cups chicken broth
  • 1 cup basil leaves
  • 1/4 cup parmesan cheese shredded
  • 1/4 cup heavy cream optional
  • 8 slices white or wheat bread
  • 8 slices american or provolone cheese
  • 2 tablespoons butter


  1. Preheat the oven to 400 F.

  2. Slice the tomatoes length-wise and place on sheet pan. Drizzle with 1 1/2 tablespoons olive oil and a sprinkle of salt and pepper and toss. Spread out cut side down and roast for 20 minutes. Add 3 garlic cloves to the pan and roast for another 40 minutes.

  3. In a stock pot, add the remaining 2 tablespoons olive oil and heat to medium heat. Add in the diced onion and the other 3 garlic cloves, minced. Cook for about 6 minutes until translucent and aromatic, stirring frequently. Add in the tomatoes, garlic and any juices from the sheet pan, the canned tomatoes with all the juices, chicken broth, basil leaves and salt and pepper. Stir well and bring to a boil. Lower to a simmer and let cook for about an hour.

  4. With about 20 minutes left in the soup cooking, preheat the oven to 300 F. Prepare a sheet pan with a rack on top and place in the oven. We'll use this to keep our grilled cheeses crispy until ready to serve. Preheat a skillet over medium heat and butter one side of all slices of bread. Place 2 slices on skillet butter side down. If 2 don't fit on your skillet, cook them 1 at a time. Top the slices with 2 slices of American Cheese each, then top with another slice of bread, butter side up. Cook for about 5 minutes or until browned on the bottom, flip and cook for another 5 minutes to brown on other side and melt the cheese. Place cooked grilled cheeses on the rack in the oven, then repeat with the 3rd and 4th grilled cheeses.

  5. When the soup has finished simmering, blend together with an immersion blender or using a high speed blender. Stir in the shredded parmesan cheese and heavy cream, if using. Taste and season with more salt and pepper if needed.

  6. Remove the grilled cheeses from the oven and dice into croutons. Serve the soup in bowls topped with croutons.