Tomato Soup & Grilled Cheese

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Growing up, I was never much of a soup person. I actually used to argue that it wasn’t even food, but a drink with food in it. Something about being in my early 20s changed this. It may have been influenced by my love of a bloody Mary.

One chilly fall day, something flipped in me and I felt the utmost need to have tomato soup and grilled cheese. What’s so great about this, is buying from a farmers market at this time is so easy and provides more nutrient dense produce while supporting the local agriculture. I’ve made this a couple times, mostly for my roommates, and it’s the perfect type of meal that truly warms you from the inside out.

First things first: tomatoes. I enjoy getting a variety of tomatoes for more depth in flavor. I’m not completely sure if it really does anything, but I like to tell myself it does. I mostly focus on Roma and Beefsteak while also throwing in some tomatoes on the vine as well as cherry tomatoes. The Roma tomatoes are quartered, and everything else is cut to the same size, besides the smaller tomatoes which are just thrown in.

Line a baking dish with in foil and add the tomatoes as you chop. Make sure there’s still some room in the pan before adding all the tomatoes. Chop your onion into equal sizes as the other tomatoes and add to the dish. You’ll also need to peel some garlic cloves and add them in whole. Drizzle with olive oil, sprinkle with salt and pepper, and toss some fresh basil on top. I frequently forget to get fresh basil, so I season with a heavy hand of dry basil and oregano. If you forget to season now, you can season before blending as well.

Roasting low and slow will result in sweeter, less acidic tomatoes while roasting on a higher temp will intensify the flavors and result in a more smoky taste. The goal is to balance these two possibilities. I heat my oven to 425 and bake for about 35 - 45 minutes, checking in between for the right result. I like to make sure everything looks like it’s sizzling. It should look like it’s cooked down or juiced have pooled in the bottom of the pan. The onion should look like it’s caramelized a bit (may be burnt on the edges) and the garlic won’t be completely tender but will have sweetened.

Next steps are based on what you have at home. If you have an immersion blender, you’re all set to add the tomatoes to a pot, add chicken broth to nearly cover, and start blending. If you don’t, you’ll need to use a blender. The reason this is a little more time consuming is because the tomatoes need to cool before you can blend them, otherwise the heat will cause a problem and you’ll have half-blended tomatoes exploded all over your kitchen. Once the tomatoes are cool, add to your blender. Add the juices from the pan first and use chicken broth to cover remaining veggies. Blend until smooth then add to a pot.

Once everything’s been blended and in the pot, bring the soup to a simmer. Simmering for longer will result in a thicker consistency while simmering for a shorter period will keep the soup thinner. Once the soup is near the consistency you would like, add your heavy cream. This helps cut the acidity of the tomatoes while making something rustic feel a little more luxurious. The seasonings should be fine but earlier but if you feel you need to add some more, there's no wrong time to do so. once it's all warm, it's ready to serve. With the amount of tomatoes I use, it makes a ton. It's a great thing to freeze and have on hand.

This is, of course, best served with a grilled cheese. Although I haven't always been a fan of tomato soup, I'm no stranger to a grilled cheese. It's the perfect lazy, drunk, sick, hungover, or just because sandwich. Delicious, not in the least nutritious. Which is why I enjoy it with tomato soup, so I can tell myself I'm getting a good fill of veggies as well.

I start with homemade sourdough and try to slice it thinly. We didn't have a serrated knife at the time of the picture above, so the bread ended up being thicker than I originally intended. Butter both sides and add it to a pan on low-medium heat. Once the start to warm on those sides, flip them and add the cheese to one piece on the previously toasted side. I find that Havarti is a great mild, stretchy cheese that really compliments gruyere. Add the other slice to the slice with cheese and wait for it to get crispy on the pan-side-down slice, then flip.

If it's getting crispy before the cheese is having enough time to melt, turn the heat down and/or add a bit of water and a lid to the pan. This will create steam that helps melt the cheese. If you're feeling crazy, you can also add some cheese directly to the pan, let it bubble, and put the grilled cheese directly down in it. This will give it a nice, crispy, cheesy outer crust.

Serve together for a hearty meal that will warm you up from the inside out.

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Ingredients For Soup:

• 4 Beefsteak tomatoes, cut to size of the Roma tomatoes

• 6 Roma tomatoes, quartered

• 1 container Grape tomatoes, whole

• 8 Cocktail tomatoes, whole

• 2 white onions, cut to size of the Roma tomatoes

• 1 head of garlic, peeled

• Seasonings: basil, oregano, s&p

• Chicken broth

• Heavy cream

Directions For Soup:

• Preheat oven to 400º

• Chop Roma and Beefsteak tomatoes then white onion. Peel garlic cloves of a head of garlic.

• Add the ingredients in a baking dish. Drizzle with olive oil and season (with a heavy hand for the herbs). Bake for around 30 min. Everything should be sizzling when you remove.

• There are two ways to move forward:

  • Immersion blender: add roasted veggies and juices to a large pot. Once all veggies have been roasted, add chicken broth. Leave the top layer uncovered since you can always add more, but can’t take it away. Then blend away!

  • Regular blender: works almost the exact same, but takes a little longer. With a regular blender, you have to wait for the veggies to cool a bit, otherwise hot tomatoes would explode all over your kitchen. Add tomatoes and juices into the blender and mostly cover with chicken broth. Blend away

• Once the veggies have reached your ideal smoothness and are in the pot, warm on medium-low heat. Add more chicken broth and seasonings as needed.

• Stir in some heavy cream to round out the acidity. This will also make it smoother.

• Let everything simmer for around 5 – 10 minutes to meld all flavors before serving.

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Ingredients For Grilled Cheese:

• Sourdough

• Havarti

• Gruyere

• Provolone

• Butter

Directions For Grilled Cheese:

• Slice your bread and butter both sides. Add two slices to a pan on medium–low heat.

• Once the bread is warm, flip and add cheese to the toasted side. I add Havarti first, then gruyere. Adding provolone can help with the cheese pull.

• When bread is golden brown, flip to toast the other side.