Pre-heat air fryer to 225ºF.

Toss the cherry tomatoes in a bowl with the olive, balsamic vinegar, salt and pepper. Air-fry the cherry tomatoes for 45 minutes, tossing them at least 3 times during the cooking time. The tomatoes should be soft and some of them will burst open. Let the tomatoes cool down a little and then stir in the fresh parsley.

Pre-heat your outdoor grill to medium-low heat. Brush both sides of the Brie wheel with olive oil and sprinkle with Italian seasoning, if using.

Slice the bread into ½ inch slices. If you are using baguette, slice it on the bias. Brush one side of the bread with olive oil. Grill the bread on both sides until lightly browned. Set the bread aside on your serving platter.

Place the Brie wheel directly on the grill grate. After 3 minutes or so, when the Brie has grill marks on the bottom, flip it over and mark the second side. Lower the flame on your grill and let the Brie heat through until it is soft and melted, another 5 to 10 minutes. The Brie will be soft to the touch and start to expand a little. Watch carefully and remove the Brie before the rind cracks and the cheese starts to leak out. Transfer the wheel to your serving platter.

Drizzle the Brie with balsamic glaze (if using) and sprinkle the basil on top. And serve immediately with the toasted bread slices and roasted tomatoes.