Preheat the oven to 375F°. Add the cherry tomatoes, sliced garlic, and fresh herbs to a large cast-iron skillet. Cover with the olive oil, season with a pinch of salt, and toss to combine. Roast for 35-40 minutes until the tomatoes are soft and caramelized.
Preheat the grill over high heat. Coat each slice of bread with a good amount of olive oil on both sides. Set aside.
In a food processor, combine the feta, olive oil, and water. Blend until smooth and creamy.
Grill the bread until slightly charred and crisp, just a minute or so per side. Transfer the bread to a cutting board and cut each piece in half.
Spoon the feta cheese into a bowl. Add the roasted tomatoes over top, along with a generous drizzle of the oil from the skillet. Top the tomatoes with a few thyme and oregano leaves, flaky sea salt, and freshly cracked black pepper. Serve the bread alongside.
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