Roasted Tomato-Basil Soup with Grilled Cheese Croutons

I went to the Union Square farmers market expecting to be inspired by the first signs of fall-butternut squash, figs, etc.  But instead, I saw cases and cases of local tomatoes, having their last hurrah of the summer.  So, to salute the end of summer and to make sure those tomatoes didn't feel abandoned, I made a roasted tomato-basil soup with grilled cheese croutons.

There are plenty of recipes out there that use canned tomatoes, but I wanted to make one that used fresh plum tomatoes, roasted to give them and intense sweet flavor.  

abcd

It wasn't even that high maintenance.  I simply laid out the halved tomatoes, onion wedges, and whole garlic cloves on a baking sheet, drizzled with olive oil, salt, and pepper and roasted them.  Then I pureed all of that, and simmered the mixture along with some red wine, balsamic vinegar, and chicken stock.  For the grilled cheese croutons, I just made some good old grilled cheese sandwiches and cut them into bit sized chunks.  Might sound simple, but there's just something so good about tomato soup and grilled cheese.  Something that shouldn't be messed with.

Nutritional Highlights:  This soup is incredibly healthy.  While a lot of vegetables and fruits lose nutrients when cooked, tomatoes actually have higher levels of heart-healthy and cancer-preventing phytochemicals.  The problem with tomato soup at restaurants is that they use tons of heavy cream and salt, making it incredibly high in fat and sodium.  My version was cream free (although I added a little bit of half and half to Jeff's bowl because he insisted on a creamy soup) but I thought it was flavorful and creamy enough without it.  I made my grilled cheese with high-fiber whole wheat bread and low fat cheese.  This is a great, healthy way to use up all those summer tomatoes.  You can even freeze some for the winter!

Roasted Tomato Basil Soup

Serves 4

• 3-4 lbs plum tomatoes
• 1 yellow onion, large dice
• 6 cloves of garlic, peeled (4 left whole for roasting and 2 minced for sauteeing)
• 4 tbs olive oil, divided
• 1/3 cup dry red wine
• 2 cups chicken stock
• 1 tbs balsamic vinegar
• 6oz can tomato paste
• 1/4 cup fresh basil, finely chopped (and some extra set aside for garnish)
• 1 teaspoon sugar (optional)
• 1/2 tsp red pepper flakes
• 1 tsp kosher salt
• 1/2 tsp freshly ground black pepper
• Optional: 1/4-1/2 cup regular or fat free half-and-half if you want it to be a little creamier

Preheat oven to 375.  Cut plum tomatoes lengthwise and cut the onion into large chunks.  Lay the tomatoes, onions, and 4 garlic cloves onto a large baking sheet lined with parchment or foil.  Drizzle with 3 tablespoons of olive oil and season generously with salt and pepper.  Roast for 50 min to 1 hour and allow to cool.

Once the roasted tomato/onion/garlic mixture has cooled a bit, transfer it to a blender and puree until smooth.  

In a medium-sized pot over medium heat, add 1 T olive oil, 2 cloves minced garlic, red pepper flakes, salt, and pepper. Cook about 1-2 minutes until garlic is fragrant. 

Pour in the pureed tomato mixture and cook about 5 minutes. Then add the tomato paste, sugar, chopped basil, red wine, chicken stock and balsamic vinegar and stir to combine.  Allow the mixture to come to a boil and then reduce to low and allow it to simmer for 30 minutes to an hour.  

If you feel the soup is still not smooth enough, you can run through the blender again or use and immersion blender.  Taste and season with additional salt and pepper as needed.

For the Grilled Cheese Croutons:

• 4 pieces whole wheat bread
• Cheese of you choice: I mixed low fat mozzarella, low fat cheddar, and full fat asiago cheese because that's what I had in my fridge.
• Butter or I can't believe it's not butter (or olive oil spray)

Spread a very thin layer of butter or butter substitute on both sides of bread.  You could also just use olive oil spray but I'm a grilled cheese purist.  

Heat a large skillet over medium heat.  Place the bread in the pan so it can get crispy on one side.  Once brown and slightly crisp on that side, flip the bread and add the cheese to the crispy side.  Allow the cheese to melt while the other side of the bread gets cripsy.  Once cheese is melted, put the slices together to make two sandwiches.  Continue to cook, flipping as needed until the cheese is completely melted and bread is desired amount of crispness.  

Remove sandwiches from pan and allow to cool for a few minutes.  Cut the sandwiches into crouton sized pieces and serve along with the hot tomato soup.  Enjoy!