Place halved tomatoes on sheet pan with garlic. Sprinkle with 1 tsp salt, maple syrup, and olive oil. Gently mix and then roast in a 375 degree oven for 30 minutes. Remove from oven and let cool. Gently remove the skins from the tomatoes.
Transfer tomatoes and garlic to a large soup pot adding basil and vinegar. Using an immersion blender, blend until smooth. If you don’t have an immersion blender, strain the soup through a sieve to create the smooth texture. Over medium heat, bring the soup to a hot temperature to serve. Salt and pepper to taste. Serve with parmesan crostini or croutons, a drizzle of olive oil or an herb pesto, if desired. Serves 6-8.