Heat olive oil in a large pot. Add onion and garlic and cook until onions are translucent and begin to caramelize. Add tomatoes, butternut squash, and vegetable broth and bring to a simmer.
Add thyme, oregano, salt, pepper, and red pepper flakes. Simmer for 15-20 minutes until the squash is tender.
Use an immersion blender or transfer to a high-speed blender and blend until smooth. Transfer the pureed soup back to the pot and add cream (or coconut milk). Taste and add more seasoning if needed.
Serve with grilled cheese or crusty bread. Enjoy!
Recipe by For the Love of Gourmet at https://fortheloveofgourmet.com/butternut-squash-tomato-soup/