Roasted tomato soup with grilled cheese croutons: a simple, flavorful, and incredibly delicious spin on classic tomato soup and grilled cheese!
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I've been on a soup and sandwich kick lately. So let's smack 'em together into one recipe!
If you've been around for a while, you might notice my 'kick's. There was the pasta kick, the beef kick, the Hispanic food kick, I mean, I go on food type binges all the time. And this past month has been no different with soups and sandwiches. My poor husband (he hates soup. Except chicken and gnocchi soup, he loves that. Go figure).
This really came around because we had some serious cold snaps here in South Florida (talking 20s in the AM!) for the last month and I love cozy soups and sandwiches when it's cold. I especially love tomato soup. Mostly because Brian makes me his classic tomato soup when I'm sick, and I craved it the entire time I was preggo with Greyson, so it holds a good hearty part of the food section of my heart.
In this recipe, I decided to go past plain ole tomato soup and give it a good, well-loved, homemade touch by roasting some tomatoes (and roasting garlic with it! Roasted garlic is pure magic, people!) and putting grilled cheese sandwich 'croutons' to eat with it. Total comfort food, and actually this would be perfect to use up all your summer tomatoes at the beginning of autumn.
And, the best part? While this is comfort food, it's also HEALTHY.
OMG, the lady with the whiskey bacon macaroni and cheese recipe is talking about healthy?!
Yeahhh...I guess. It wasn't intentional or anything. And the grilled cheese ain't the healthiest thing, but still. This stuff will help your comfort food cravings and not hurt your waistline, if you're into that.
My tip for the best roasted tomato soup is to get those good, ripe tomatoes. Like I said, this will be great for your summer tomatoes at the end of summer's season, or if you live in a perpetually (mostly) hot area like I do. They'll be sweeter and give off great flavor.
I used my awesome panini maker (I've been OBSESSED!) to get those lines on the grilled cheese croutons, but make them however you want; you could cut your sandwiches into shapes or strips --dunking grilled cheese sticks sounds fun-- or even just eat them the good old fashioned way. As a sandwich.
Sandwiches that are eaten as sandwiches are the new retro chic y'all. #foodtrends
For more bowls of pure comfort cravings check out:
chicken and gnocchi soup
french onion soup
chicken and dumplings
beef stew
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📖 Recipe

Roasted Tomato Soup with Grilled Cheese Croutons
Roasted tomato soup with grilled cheese croutons: a simple, flavorful, and incredibly delicious spin on classic tomato soup and grilled cheese!
Ingredients
Tomato soup
- 4-5 plum tomatoes, cut in half length-wise
- ½ head garlic, about 6-7 cloves, skin on
- ¼ cup olive oil
- 2 medium sized carrots, peeled and roughly chopped
- 1 small onion, large dice
- 2 tablespoon tomato paste
- 1 28 oz can San Marzano tomatoes, crushed
- 4 cups low sodium chicken broth
- 2 sprigs fresh thyme
- 8 fresh basil leaves
- 1 bay leaf
- 2 tablespoon sugar, to taste
- kosher salt and freshly cracked black pepper, to taste
- cream or half and half
Grilled cheese croutons
- 4 slices sourdough bread
- 4 slices cheddar cheese
- softened butter
Instructions
- Preheat oven to 400 degrees F.
- Place tomatoes cut side up with the onion, carrots and garlic on a rimmed baking sheet or oven safe dish. Drizzle with oil and sprinkle salt and pepper over the top.
- Roast for 40-50 minutes, until tomatoes are slumped looking, turning golden brown, and other veggies are roasted and browned.
- In a heavy bottomed pot or dutch oven, add the roasted vegetables, San Marzano crushed tomatoes (juice and all), chicken stock, and fresh herbs. Bring to a low simmer over medium-low heat, then add bay leaf. Cook for 20-25 minutes.
- While tomato soup is cooking, make grilled cheese croutons by spreading butter on outer sides of the bread and placing two slices of cheese in the middle. Press sandwich between a panini press, or cook on a pan over medium heat, flipping when bread is browned.
- Cut the sandwiches into 1 or 2 inch squares. To make them crunchier, like a crouton, put sandwich squares onto an oven safe baking sheet or dish and set oven to 200 degrees until soup is complete OR until the croutons have come to your preferred crunchiness.
- Once soup has cooked for 20-25 minutes, taste and season with sugar (tomato soup can be acidic) and salt and pepper to taste. Carefully transfer soup to a blender, removing thyme stems and bay leaf, and puree soup until there are no large chunks left, then strain through a fine mesh sieve into a bowl or pot so ensure smooth soup.
- Serve with grilled cheese croutons immediately. Add a drizzle of cream to each bowl as desired.
- Store soup in an airtight container in the fridge for up to 5 days or in the freezer for up to 3 months.
Nutrition Information:
Amount Per Serving: Calories: 215
Don't forget to PIN this roasted tomato soup recipe!

Eden Westbrook is the recipe developer, writer, and photographer behind Sweet Tea and Thyme. A classically trained chef, Eden has inspired home cooks into the kitchen with cultural comfort foods, easy family-friendly eats and sweets, and glorious spreads for date night and entertaining since 2015.
Rebecca | Let's Eat Cake says
That tomato soup looks seriously amazing! And I love the grilled croutons!
Jill says
One of my favorite comfort food combos - grilled cheese and tomato soup. Love the drizzle of cream on top of the soup too!
Maggie @ Mama Maggie's Kitchen says
Such a classic and always a favorite. Never tried making the grilled cheese croutons though. Pinning for later!
Beth says
As you say, roasted garlic is absolutely magic! I'm not sure if I like that better or the grilled cheese croutons!! Genius!
Emma says
There is nothing about this soup I don't love! It's so comforting and nostalgic but properly finessed!