Combine the marinade ingredients in a bowl or blender and pour over the steak. Marinate overnight.: The smell of balsamic vinegar mingling with grated garlic and chopped herbs is the first sign the steak is on its way to greatness, a heady, slightly sweet aroma that will deepen as it soaks. Leave the flank steak covered in the fridge so the flavors penetrate; you will notice the meat darken slightly and feel tacky to the touch when the marinade has done its work. This slow infusion is why I insist on overnight time when possible, it tenderizes and concentrates flavor. A common mistake is using too much acid for too long which can make the surface mushy, so keep the balance and don’t marinate for multiple days. When you remove the steak, let it sit at room temperature for twenty to thirty minutes before grilling to ensure more even cooking and a better crust.
Combine the cherry tomatoes with salt. Stir in the vinegar, garlic and olive oil.: As you toss the halved cherry tomatoes with a pinch of salt, they begin to release bright juices, creating a lightly saucy base that clings to the arugula . Stirring in the extra splash of balsamic vinegar and the minced garlic wakes up the tomatoes and adds an aromatic lift, while the olive oil gives a glossy coating. The sound here is subtle, just a soft slicking as the dressing coats the tomato halves, and the scent becomes fruity and piquant. Avoid over salting, which can drown the tomato sweetness, and don’t dress the salad too far in advance or the leaves will wilt and the tomatoes will become too soft.
Heat the grill over high heat, spray the grates and grill a few minutes on each side, until cooked to your taste. Let it rest a few minutes before slicing.: When the grill is searing hot you will hear an energetic sizzle as the steak hits the grates and watch the surface develop a deep mahogany crust. That crust seals in juices and creates smoky, caramelized flavors thanks to the balsamic and sugars from the marinade. Grill times vary depending on thickness, but visually look for a pronounced char and juices starting to bead at the surface. After pulling the steak from the heat, allow it to rest tented for several minutes so the juices redistribute and the texture becomes tender rather than leaking out when sliced. A frequent error is slicing immediately; this causes loss of juice and a drier bite. If flare ups occur, move the steak to a cooler zone to avoid burning while still achieving a good sear.
Toss the arugula with the tomato mixture.: The moment you fold the peppery arugula into the tomato mixture the salad comes alive, the leaves wilting just slightly under the warmth and taking on the dressing’s acidity. The aroma shifts to a fresher, herbaceous note and the contrast of textures becomes clear, with tender tomato juices and crisp leafy greens. Toss gently so the arugula retains some structure, and taste for seasoning, adjusting salt if needed. Avoid overdressing, which can make the leaves soggy; it’s better for the salad to be lightly coated so it sits well on the warm steak.
Slice the grilled skirt steak into thin slices and place on a platter, scatter the arugula-tomato salad over the steak and serve right away.: When slicing, cut across the grain of the steak into thin ribbons to maximize tenderness; you’ll see clean, glistening slices that reveal a juicy interior and a charred edge. Arrange the meat on a serving platter and scatter the tomato and arugula salad over the top so each slice gets a hit of acidity and peppery green. The final plate smells of smoke, garlic, and bright vinegar, and visually it pops with red and green against the brown steak. A common misstep is slicing too thickly which makes the meat feel tough, so thin, angled cuts are best. Serve immediately so the contrast of warm steak and cool salad is at its peak.