When I lived in New York, my friend Sara invited me to lunch at her house, and while we chatted she made grilled cheese sandwiches and warmed up a yummy box of tomato soup from Trader Joes. I adore this meal. It’s on my list of comfort meals for sure. But until Sara served it to me, I had considered it too plebian or boring for guests.
I had a lovely shift in thinking that day. Why wouldn’t I serve this comforting, beloved meal? And why stress out about a fancy meal, when I can be relaxed and enjoy my company — and serve a known crowd-pleaser at the same time? All of sudden, I could invite people over for lunch and it didn’t have to be a big deal. Which means I was more likely to invite someone over in the first place!
I hope it’s safe to say, most people love tomato soup and grilled cheese sandwiches. It’s definitely a favorite around our house. I can tell you I am fully on board with boxed soup, but for today’s recipe in my Crockpot & Slow Cooker Series, it’s all about Homemade Tomato Soup. It’s pretty much one of those put everything into the slow cooker kinds of recipes, set it and forget it. There are also stovetop instuctions if you want to skip the crockpot. Oh! And there’s a recipe for Pesto Grilled Cheese Sandwiches below too.
I’m always feeding a crowd, so I included a recipe to feed 10-12. If you have a smaller family, don’t worry, just halve all of the ingredients. However, I will say the leftovers don’t go to waste! They are great to send in a lunch box or pull out for a quick meal the next day.



Tomato Basil Soup Recipe for Crockpot or Stovetop
Makes 10-12 servings
Ingredients:
3 large carrots, peeled and roughly chopped
2 celery stalks, diced
2 medium sweet onions, roughly chopped
4 cloves garlic, peeled and left whole
2-3 teaspoons salt (start with less and add to taste)
1/4 teaspoon fresh ground black pepper
4 (28-ounce) cans whole peeled tomatoes
1 quart low-sodium organic free-range chicken broth
1/4 to 1/2 cup fresh basil leaves, roughly chopped, plus more for garnish
half and half or heavy cream (optional)
Freshly grated Parmesan (for garnish, optional)
Slow Cooker Version:
Place all of the ingredients, except for half and half and Parmesan into a very large slow cooker. Top with the lid and cook on high for 4 hours or low for 5-7 hours. The vegetables should be very soft at that point. If not, cook for another hour or so.
Use an immersion blender to puree the soup. Alternatively, work in batches and puree soup in traditional blender. Be extra careful and don’t fill the blender too full, or it will splatter and escape from the lid.
To the pureed soup, add the half and half. Taste and add more salt and pepper, if needed. Ladle into bowl and sprinkle with freshly grated Parmesan and extra basil.
Serve with biscuits, hot rolls, grilled cheese sandwiches, or breadsticks and a large green salad.
Stove-top Version:
Combine all ingredients in a heavy lidded pot or Dutch oven over medium-high heat. Bring to a boil, then turn heat down to low, and simmer, covered, for about 2 hours, until flavors are blended and vegetables are soft. Allow the soup to cool slightly. Then puree in batches in a blender until very smooth. If you like a thinner consistency, add a little bit more stock or water. Serve immediately, or transfer the soup back to the pot and keep on low until your guests arrive.
Garnish with more fresh basil and some grated Parmesan cheese.

Pesto Grilled Cheese Sandwich Recipe
To make about 6-8 sandwiches
Note — this pesto has much less oil than traditional recipes so it doesn’t saturate through the bread and make it soggy. Add just enough to make it spreadable.
Ingredients:
1 large loaf sourdough or another kind of bread, sliced
1 lb. mozzarella, sliced
Butter, for cooking
4 cups fresh basil leaves
1/4 cup pine nuts
1/4 cup grated Parmigiano-Reggiano
1-2 garlic cloves
2-4 Tablespoons extra virgin olive oil
Instructions:
1. Have a large skillet or griddle ready.
2. Prepare pesto — place basil, pine nuts, Parmigiano-Reggiano, and garlic in a food processor. Pulse until finely chopped. Add the olive oil a little at a time through the feed hole while pulsing. Scrape down sides as needed.
3. Lay all the bread slices open and place the sliced mozzarella on half of the bread slices. On the other half, spread a little of the pesto. Close the sandwiches and spread butter on the outside of every sandwich.
4. Heat the skillet or griddle to medium-high heat and cook the sandwiches until golden on each side, lowering the heat if necessary so they don’t burn. Serve immediately.
P.S. — Find all the recipes in this series here.
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