Begin by preparing your pastry dough: combine flour with a pinch of salt in a bowl, then cut in the cold butter using a pastry cutter or your fingers until the mixture resembles coarse crumbs. Add a splash of vinegar and cold water, mixing just until the dough comes together. Wrap in plastic and chill in the fridge for at least 30 minutes.
While the dough chills, slice the heirloom tomatoes thinly and lay them out on paper towels to absorb excess moisture. Pat them gently to remove surface water, which helps prevent sogginess.
Preheat your oven to 375°F (190°C). Roll out the chilled dough on a floured surface into a rustic circle, about 12 inches in diameter. Transfer it to a parchment-lined baking sheet or tart pan, and trim any uneven edges.
Spread a thin layer of crumbled cheese over the base of the pastry, leaving a 1-2 inch border around the edges. Drizzle with a little olive oil over the cheese.
Arrange the sliced tomatoes over the cheese, overlapping slightly and covering most of the surface for a colorful, layered look. Sprinkle chopped herbs over the top, and season lightly with salt and pepper.
Fold the edges of the pastry border over the tomatoes, pinching gently to create a rustic, crimped edge. Brush the crust with a little olive oil for extra golden color.
Bake the tart in the preheated oven for about 30 minutes, or until the crust is golden and flaky, and the tomatoes are bubbly and slightly caramelized around the edges. The aroma of baked herbs and roasted tomatoes will fill your kitchen.
Remove the tart from the oven and let it rest for a few minutes. Drizzle with a little extra virgin olive oil, and sprinkle with fresh herbs or a pinch of flaky sea salt for flavor enhancement.
Slice the tart into wedges and serve at room temperature or slightly warm. Enjoy the crispy crust paired with juicy, smoky tomatoes and the rich, melty cheese for a delightful, rustic flavor.