Let’s be honest. There are some food combinations that just feel right. And today, we’re diving headfirst into one of the absolute best: Grilled Cheese & Tomato Basil Soup. It’s the epitome of comforting, a ridiculously easy weeknight dinner, and a fantastic way to use up leftover bread. Seriously, can you not love this?
Sauté the Aromatics: In a large pot or Dutch oven, heat the olive oil over medium heat. Add the chopped onion and cook until softened, about 5-7 minutes. Add the minced garlic and cook for another minute until fragrant. Don't let it burn!
Build the Flavor: Stir in the crushed tomatoes, diced tomatoes (with juice), vegetable broth, tomato paste, dried basil, dried oregano, red pepper flakes (if using), and bay leaf.
Simmer & Season: Bring the soup to a simmer, then reduce the heat to low, cover, and let it simmer for at least 20 minutes. This allows the flavors to meld beautifully. Season with sugar, salt, and pepper to taste.
Creamy Finish (Optional): If you’re using it, stir in the heavy cream during the last 5 minutes of simmering. Remove the bay leaf before serving.
Now, for the Grilled Cheese (About 10-15 minutes):
Butter the Bread: Spread the softened butter evenly on one side of each slice of bread.
Cheese It Up: Sprinkle a generous amount of shredded cheese (about 2 oz) evenly over the unbuttered side of two slices of bread.
Grill to Perfection: Heat a skillet (cast iron is fantastic!) over medium-low heat. Place the sandwich on the skillet, butter-side down.
Golden Brown & Gooey: Cook for 3-5 minutes per side, or until the bread is golden brown and the cheese is completely melted and gooey. Press down gently with a spatula to ensure even grilling.
Assembly & Serving:
Ladle & Serve: Ladle the hot tomato basil soup into bowls.
Top It Off: Place a grilled cheese sandwich on top of each bowl of soup.
Enjoy Immediately: This is best enjoyed warm, while the soup is steaming and the grilled cheese is perfectly melted.