Bring a large pot of water to a boil. Prepare a large ice bath in a separate bowl. Cut an "x" into the stem end of each tomato and boil the tomatoes for one minute. Carefully remove and place in the prepared ice bath.
When tomatoes are cool, remove the skins from the tomatoes and discard (this should be quite simple to do because of the boiling process).
Heat olive oil in a dutch oven or large pot over medium heat. Add in the onion and cook, stirring occasionally, until onion begins to soften - 4-5 minutes. Season with salt.
Add garlic to the pot and cook for another 1-2 minutes until it's fragrant.
Mix in Calabrian chilies or crushed red pepper and cook for another 1-2 minutes.
Turn the heat up to medium high, add in in the peeled tomatoes, pour in the vegetable stock and bring the mixture to a boil. Reduce the heat to medium low and simmer for 40 minutes. Season with a few more pinches of salt.
Blend the mixture with an immersion blender or carefully add the soup contents to a high powered blender like a Vitamix to puree and return to the pot.
Stir in the heavy cream and heat the soup over medium low for 15 more minutes. Season with more salt as needed.
Ladle soup into bowls, top with basil cream and basil and serve with sourdough dippers along side.