Prep the Skewers: Soak wooden skewers for at least 30 minutes.
Prep the Tomatoes. In a bowl, toss the cherry tomatoes with olive oil, salt, and pepper and thread 4–5 tomatoes onto each skewer.
Make the Herb Vinaigrette. In a blender or small food processor, combine the parsley, mint, shallot, olive oil, red wine vinegar, honey, salt, and pepper. Blend until smooth and bright green.
Grill the Skewers. Heat a grill to medium-high. Grill the skewers for 6–8 minutes, turning occasionally, until the tomatoes are lightly charred and blistered but still holding their shape.
Assemble. Spread the herb vinaigrette onto the bottom of a serving platter.
Arrange the grilled tomato skewers on top, sprinkle with crumbled feta and fresh mint leaves, then finish with flaky salt and a drizzle of olive oil.