Preheat oven to 350°F
Rinse, dry and cut tomatoes in half lengthwise. Peel garlic and halve larger cloves.
Transfer tomatoes / garlic to a large baking sheet, drizzle with olive oil and sprinkle generously with salt and pepper.
Use your hands (or a spoon if preferred) to stir tomatoes and garlic until well coated.
Place sheet in the oven and roast for 60 minutes.
Spoon tomatoes and garlic into a large pot on the stove top. Turn heat to medium high.
Add vegetable broth, red wine, white wine vinegar, bay leaf, fresh basil and Italian seasonings. Bring ingredients to a boil.
Reduce heat down to low, cover and simmer 15-20 minutes, stirring occasionally.
Remove bay leaf and use an immersion blender to puree soup until smooth! If desired, blend in a splash of heavy cream or your non-dairy milk of choice. (*Tip: you can also transfer soup to a regular blender to puree if you don't have an immersion blender).
Serve and enjoy!