Mini Classics: Tomato Soup with Grilled Cheese Bites

In times where we’re all looking for a little comfort- be it wearing pajamas while we work from home, splurging on some online shopping, or indulging in takeout a few times a week- I’ve turned to tasty recipes that remind me of home and my family- many of whom I haven’t seen in months since the pandemic began.

Grilled cheese and tomato soup are by no means anything new or innovative- but my mom has a way of making them a fun appetizer when we used to be able to have Sunday night “The Walking Dead” and “90 Day Fiancé” binge-watch-fests together. Her tomato soup, made from scratch and served in small glasses- can only be improved when I get to dunk a miniature double grilled cheese into it.

These are one of my favorite comfort foods to whip up when I’m feeling a little down- and I think the ongoing social distancing protocols have us all feeling a little glum, really.




  • 1 tablespoon extra-virgin olive oil
  • 1 sweet onion, diced
  • 2 garlic cloves, minced
  • One 28-ounce can plum tomatoes
  • 2 cups vegetable or chicken broth
  • 1 bay leaf
  • Kosher salt and freshly ground black pepper
  • ⅓ cup half-and-half


  • 3 tablespoons unsalted butter, at room temperature
  • 9 slices white bread
  • 12 slices American cheese
  • Skewers, for finishing (optional)


1. MAKE THE SOUP: In a large saucepan, heat the olive oil over medium heat. Add the onion and sauté until translucent, about 5 minutes. Add the garlic and sauté until fragrant, about 1 minute.

2. Stir in the tomatoes and use a wooden spoon to lightly crush them. Stir in the broth and bring to a simmer. Add the bay leaf; season with salt and pepper. Let the soup simmer until good flavor develops, 20 to 25 minutes.

3. Transfer the soup to a food processor or blender and blend until smooth. Stir in the half-and-half.

4. MAKE THE GRILLED CHEESE BITES: Butter one side of each piece of bread. Build three double-decker sandwiches with two pieces of cheese between each layer of bread, making sure the buttered sides of the bread are facing out.

5. Heat a large skillet over medium heat. Reduce the heat to low and place the sandwiches in the pan, working in batches if necessary. Cook until the bread is evenly golden brown, flipping once, about 5 minutes per side.

6. Cut the crusts off the sandwiches, and cut each sandwich into four triangles. Skewer each sandwich, if desired.

7. To serve, ladle the soup into single-serve cups and top each with a sandwich.


Wonderful, warm and cheesy taste aside- the presentation of these little soups and sandwiches are adorable and perfect for the next time we can have parties again. They’re good for any occasion- but I prefer making them when I have company on a rainy day.

But with Summer on the horizon- I don’t know how many more rainy Spring days we have left- so I’ll have to find some more BBQ/cookout-appropriate recipes to try out until the next seasonal thunderstorm rolls through New England.


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Hi! I'm Ashley. I'm a blogger and a radio personality with a makeup and shoe addiction based out of Boston and the Pioneer Valley. These are my (mis)adventures.

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