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Prep: Preheat oven to 425°F (220°C). Line a baking sheet with parchment paper or grease lightly.
Roast Tomatoes: Toss the halved cherry tomatoes with the olive oil, sea salt, and black pepper. Spread them on the baking sheet and roast for 10–12 minutes until soft and bursting, then remove from the oven.
Assemble: Arrange the flatbreads on the baking sheet. Spread a thin layer of basil pesto over the crusts, then distribute the crumbled goat cheese and roasted tomatoes evenly on top.
Bake: Bake for 8–10 minutes until the edges of the flatbread are golden brown and crisp, and the cheese is thoroughly warmed.
Finish: Remove from the oven, immediately pile the fresh arugula over the hot flatbreads, and sprinkle with optional red pepper flakes before slicing.