Preheat your oven to 375F.
Place the tomatoes, the whole garlic cloves and the shallots in a large baking dish (I used a 9x13 casserole pan). Drizzle over 2 tablespoons of olive oil and 1 tablespoon of maple syrup. Sprinkle over 1 teaspoon of sea salt and give everything a quick mix. I like to use my hands since the pan will be pretty full.
Bake the tomatoes, garlic and shallots for an hour to an hour and 15 minutes. You are looking for the tomatoes to have cooked down quite a bit.
Remove from oven and let cool for about 15 minutes.
In a blender, place half of the tomato mixture and 1 ¼ cups of vegetable broth. Blend until perfectly smooth (about a minute). Repeat this step once more. Make sure to pour in all the juices from the pan as well. You don’t want to waste all that amazing flavour from the pan.
Transfer the puréed tomatoes, garlic and shallot to a large saucepan. Add in the dill, coconut milk, maple syrup, sea salt, pepper, and chili flakes. Turn the heat up to medium-high and stir until combined. Taste the soup for seasoning.*see note
Let simmer for 15 minutes.
Serve and enjoy!
This recipe will require a bit of taste testing since two flavours can vary immensely based on the ingredients you are using. I would recommend you taste the soup in the process to ensure the soup has just the right amount of sweet and salty. If your tomatoes are in season, you may be able to cut out a tablespoon or so of maple syrup. Mine were not in season so I added that tablespoon to balance out the acidity of the tomatoes. When picking your tomatoes, try to pick ones that are ripe and varieties that are sweeter such as cherry tomatoes and tomatoes on the vine. I like to mix the varieties of tomatoes when I make tomato based dishes. I like to steer clear of pale red tomatoes as they are more than likely going to lack natural sweetness. Although roasting them will bring out that natural sweetness, it’s always best to start with the best quality ingredient you can find. That goes for any recipe for that matter. Saltiness is another factor that can vary in this soup depending on the vegetable broth you are using. I think a good rule is to start with a little more than half of the amount of salt called for in a recipe and adjust as you go. Remember, you can always add but you can’t take away when cooking.