Prepare the oven. Preheat the oven to 400°F (200°C). Place the cherry or grape tomatoes on a rimmed baking sheet or in a small baking dish.
Season the tomatoes. Drizzle the tomatoes with 2 tablespoons of olive oil. Sprinkle with Italian seasoning, salt, and black pepper, then toss gently until evenly coated.
Roast. Roast the tomatoes for about 20–25 minutes, or until softened, juicy, and beginning to burst. Remove them from the oven and allow them to cool slightly.
Blend the feta. Add the feta cheese, Greek yogurt, 2 tablespoons olive oil, lemon juice, and garlic to a food processor. Blend until smooth and creamy, stopping to scrape down the sides as necessary.
Plate the dip. Spread the Whipped Feta Dip with Roasted Tomatoes base onto a shallow serving plate or bowl, creating gentle swirls with the back of a spoon.
Add the tomatoes. Spoon the warm roasted tomatoes and some of their flavorful juices over the creamy feta mixture.
Finish and serve. Sprinkle with freshly chopped herbs and serve with vegetables, crostini, pita bread, or crackers.
Notes
Cherry and grape tomatoes both work beautifully. Choose ripe tomatoes with good color and firm skins for the best roasted flavor.