I really thought we were in the clear with the winter storms. It has been a cold but fairly snowless winter here in the Tri-State Area. It was 60 degrees here last week, the groundhog didn’t see his shadow…bring on early spring! Well, Mother Nature isn’t done yet.
With a snow storm on the horizon for tomorrow, Tyler Florence’s tomato soup with my easy grilled cheese dippers is the perfect warm you up meal. Not only is it creamy and hearty, but dipping grilled cheese in your soup? It’s fun for the whole family!

Start with the key ingredient – tomatoes. Part of what gives this soup its rich tomato flavor is the combination of multiple varieties of tomatoes. Pick up whatever looks good at the store that day – heirlooms, vine tomatoes, romas, plum or cherry. Go wild! The more varieties, the richer the flavor.

Next, add the sliced onion and garlic to the baking sheet and drizzle with olive oil, salt and pepper. Put the baking sheet in the oven and allow these ingredients to roast and caramelize. You want to get the brown color with the dark edges throughout. Roasting tomatoes and garlic brings out the natural sweetness and intensifies the flavor, and all the brown spots and charred edges add deep fire-roasted flavor to the soup.

Once roasted, add the tomatoes, garlic and onions to a large stock pot. Add the chicken stock, bay leaves, salt and pepper. Bring to a boil and allow to simmer for 20 minutes.

After 20 minutes, remove the bay leaves, add the chopped basil and get ready to use one of my favorite appliances – my Cuisinart Immersion Blender! This is the quickest and easiest way to turn simmer ingredients into a creamy delicious soup. Blend the soup until it is smooth.

Add the cream and stir to combine. This is going to sound redundant, but the cream really does make the soup creamy.
Now that you have a rich and creamy tomato soup, it would be sacrilege to not have grilled cheese to go with it. And just to make things fun, let’s make them easy to dip!

Three simple ingredients come together to make an ooey gooey grilled cheese – bread, cheese, and my secret ingredient…dijon mustard. Start by spreading a thin layer of mustard on one side of each slice of bread. The mustard adds a slight bite to the sandwich and cuts through the richness of the cheese. But keep the layer thin as mustard can easily overwhelm.

Next step is to add the most important part of a grilled cheese – the cheese. Any cheese goes here. Use what cheese you like, what you have on hand, what sounds good to you. I had sliced provolone and shredded cheddar in my refrigerator, both cheeses I love, so that’s what I went with. Layer on the cheese and don’t be shy. Grilled cheese is all about the cheese!
Put the two sides of the sandwich together and drizzle the outsides with olive oil. Now comes my second favorite appliance – the Air Fryer. This was my first attempt at making grilled cheese in an air fryer and I was not disappointed. Crunchy, cheesy and easy!

Air fry the sandwiches for 10 minutes on 350, flipping about 6 minutes in. Once browned, remove, cut into long strips and serve alongside the tomato soup. After a long snow day at home, make this soup to warm up and fill up your family’s stomachs, while having fun with dinner at the same time.
Roasted Tomato Soup with Grilled Cheese Dippers
Tyler Florence’s Roasted Tomato Soup is an easy and delicious way to warm up on a cold day.
Ingredients
- 2.5 lbs tomatoes various types
- 6 garlic cloves peeled
- 1 large yellow onion sliced
- tomatoes in the vine for garnish for garnish, optional
- 1/2 cup olive oil
- salt and pepper
- 3/4 quart chicken stock
- 2 bay leaves
- 4 tbsp butter
- 1/2 cup chopped basil plus more for garnish
- 2 tbsp heavy cream
Grilled Cheese Dippers
- 8 slices whole wheat bread
- 8 tsp dijon mustard
- 16 slices provolone cheese
- 16 slices sharp cheddar
- 2 tbsp olive oil
Instructions
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Preheat oven to 450.
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Core and halve the tomatoes, slice the onions, peel the garlic and place them all on a baking sheet. Add the vine tomatoes as well if you are using them.
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Drizzle with olive oil, salt and pepper. Roast for 30 minutes until caramelized.
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Remove roasted tomatoes, onions and garlic from the oven and place in a large stock pot. Set the vine tomatoes aside for garnish. Add the chicken stock, bay leaves, salt and pepper. Bring to a boil and simmer for 20 minutes.
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Remove bay leaves. Add in the basil and stir to combine.
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Use an immersion blender to puree the soup to a smoothy consistency.
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Add in the cream and stir to combine.
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Ladle the soup into bowls and garnish with basil and the vine tomatoes.
Grilled Cheese Dippers
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Spread out the bread and coat each piece with a thin layer of dijon mustard.
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Layer the cheese on one side and top with the second piece.
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Drizzle olive oil on the outside of both pieces of bread (top and bottom of the sandwich) and place in the air fryer basket.
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Air fry at 350 degrees for 10 minutes, flipping after 6 minutes.
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Remove the grilled cheese from the air fryer, cut into long rectangles and serve.
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