~ 5 pounds of fresh tomatoes from the farmers market (or grocery store - the trick is fresh firm tomatoes that smell like tomatoes), cored and cut into chunks
2 shallots (about 4 tbsp total)
2 tbsp fresh oregano
2 tbsp fresh basil
2 tbsp fresh chives
2 tbsp fresh chopped garlic
2-3 tbsp olive oil
4 tbsp pesto (I like classico if I'm not making it fresh)
1 tbsp fresh ground pepper
1 tbsp salt
1 tbsp paprika
1/2 tsp ancho chili
1/2 cup white wine
1 tsp sugar
4 cups chicken stock (can also be vegetable stock, this was what I had on hand)
1 cup heavy cream
1/2 cup fresh grated romano (or parmesan or asiago) cheese to top
Slice the herbs and fresh spices into small pieces.
In a large, heavy bottom stock pot heat olive oil (enough to thoroughly cover bottom), then brown spices and pesto slowly until golden, about 10 minutes. While these brown add salt, pepper, chili and paprika.
Deglaze with white wine, then add tomatoes, sugar and chicken stock. Simmer for about 45 minutes until the tomatoes start to break down and the liquid drops by about 1/3.
Blend with immersion blender until smooth (or if you don't have an immersion blender, a counter top one will work, but you'll need to split the pot of soup up into a few batches for blending) then return to low heat. Adjust spice and sugar level as needed (if it's too acidic you can also add a bit of baking soda - the point is that too acidic and the cream will curdle).
Stir in cream and continue stirring until heated through and nice and thick; do not boil, but a low simmer is OK if the soup is thin.
Serve in shallow bowls topped with grated cheese. And in our case with grilled cheese sandwiches with or without bacon or ham.
Leftovers can be frozen in small containers for future use; grilled cheese and tomato soup is a favorite dinner when I'm feeling crappy and/or have no energy. From the freezer, simply put it into a microwave safe bowl and thaw on low heat, then turn the heat up to high for 30 seconds to a minute and serve.
Notes: as with many of my recipes this tends toward mild spices and Mediterranean seasoning; you can add fresh chili or swap spices to fit your chosen level of heat or taste profile.
It's started to reduce, but still has a long way to go. In case you're curious, the tomatoes here are a mix of red Japanese and yellow/orange heirlooms.