Place all soup ingredients except cream into a large pot over medium-high heat until it boils.
Once it boils, reduce heat and simmer, uncovered for about 15-20 min, stirring every few min to prevent burning of tomatoes.
Add cream, then use a submersion hand blender to blend ingredients into a creamy texture.
Let come to a simmer again, being careful not to boil cream. Just reheat all ingredients together, about another 5 minutes, while wisking cream into soup.
While soup comes to temperature, place a large skillet on med-low heat.
Assemble grilled cheese sandwiches with about 1 1/2 sliced of cheese per sandwich. Butter side of bread facing you, then place in pan buttered side down.
Cook each side about 2 to 3 minutes until golden.
Remove from pan and let cool for a few minutes.
On a cutting board, cut each sandwich into bite size pieces.
Return pieces to pan. Drizzle olive oil and sprinkle Italian seasoning. Stir to coat sandwich pieces.
Coat all pieces and cook on low just a few minutes or so until olive oil is absorbed, bread is golden but not burnt.
Cheese will be gooey and fried onto some pieces!
Serve each bowl of soup with a sandwich-worth of croutons, or serve in a bowl and let everyone take what they want.