Jolly Holiday Grilled Cheese and Tomato Soup

The weather took a chilly turn yesterday with 6-8 inches of wet, heavy snow. I also received a special delivery of veggies from a neighborhood friend which could only mean one thing. Tomato soup and grilled cheese! TS + GC is a perfect pair. A comforting childhood memory - usually with a can of Campbell's, Wonder Bread, Kraft singles, and margarine - grilled cheese and tomato soup was an exciting change from PB&J. Jolly Holiday at Disneyland services soup and sandwiches with quite the reputation.

Since I had fresh tomatoes, I wanted to take advantage of them instead of canned. It was very easy, not messy, and really not time consuming either. Chop aromatics like onion and garlic with tomatoes, drizzle with oil, season with dried herbs and salt and pepper, then roast at high heat in the oven. To get a little extra char you can broil them for a few minutes which deepens the flavor. Once all the veggies are roasted and starting to break down, simmer them with chicken stock and additional herbs occasionally using a wooden spoon to further break down the tomatoes. I love dill so my secret ingredient in this soup is adding dried dill to the soup pot while everything simmers. To blend the soup to a smooth consistency you can use a variety of kitchen tools. My mom used our counter top blender when I was a kid to make cream of broccoli soup - still works perfectly today. An immersion blender, food processor, and counter top blender will all work to achieve a smooth soup.

Although Wonder Bread and Kraft single can't really lead you wrong, there are some grown up grill cheese alternatives that I really love. The most important one to me is finding a sturdy bread with a crusty edge. My current favorite is izzio sourdough bread - it comes in a half loaf at King Sooper's which is perfect because I can use half a loaf before it expires. The second thing is your cheese choice. I like using colby jack cheese, slices or shredded. Lastly, I would go with butter over mayo (I know...) or margarine. It toasts better in a pan over medium-low heat and helps the bread be crispy and golden. You can also use a panni press or flat top grilled to get a treat toast on your bread. If you want to avoid the butter all together you can make a "toasted" cheese sandwich in a toaster oven.

Grill cheese is endlessly customizable. People add all sorts of things - meat, fruit, seasoning, extra cheese - to sandwiches. I personally loved the bacon, tomato and cheddar grilled cheese I had at a local restaurant recently. Try a new spin on your grilled cheese next time like substituting provolone with garlic, herbs, or roasted veggies like broccoli and red peppers!

Fresh Tomato Dill Soup

Servings 6


  • 8 medium tomatoes
  • 1 red pepper
  • 1 white onion
  • 6 cloves of garlic
  • 2 tbs oil oil
  • Italian herb seasoning (basil, oregano, and thyme) to taste
  • salt and pepper to taste
  • 2 cups chicken or vegetable stock
  • 1 tsp dried dill
  • fresh basil


  1. Preheat oven to 450 degrees F. 
  2. Chop tomatoes in quarters or eights. Chop onion into medium sized pieces. Trim off ends of garlic and remove skins. Place tomatoes and aromatics on sheet tray covered with parchment paper or foil. Drizzle with olive oil and season with salt, pepper, and Italian herb seasoning. Roast for 25 minutes, stirring after 15 minutes. Turn up heat to broil on high for 5 minutes.
  3. Add stock to a soup pot. Bring to boil. Add roasted vegetables. Use a spoon to break down largest chunks. Add dill. Simmer for 30-45 minutes.
  4. Carefully using a ladle, transfer all contents of the pot to counter top blender or food processor. Alternatively blend directly in the pot with immersion blender. Blend on medium until smooth. Taste and season as needed. 
  5. Ladle into bowls. Garnish with thinly sliced basil. Enjoy!


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