Heat grill to high. Place the squid in a bowl, drizzle with a few tablespoons of oil, and season with salt and pepper. Grill the squid bodies and tentacles for about 2 minutes per side. Remove from the grill, let rest 5 minutes, then cut the bodies crosswise into 1/2-inch thick rings. Keep the tentacles whole.
Brush the bread lightly with oil on both sides and season with salt and pepper. Grill for approximately 1 minute per side or until lightly charred. Remove and cut each slice into 1/2-inch dice. Brush the tomatoes with oil, season with salt and pepper, and grill until slightly charred, about 1 minute; remove and coarsely chop.
Toss the squid, bread cubes, and parsley with some of the vinaigrette in a large bowl. Let stand for 10 minutes. Arrange the tomato slices along the bottom of a serving platter. Top with the squid-bread mixture. Garnish with torn mint and drizzle with additional olive oil and red wine vinegar, if desired.
Whisk together vinegar, mustard, chipotle puree, honey, and garlic in a medium bowl. Season, to taste, with salt and pepper. Slowly whisk in the oil until emulsified. Stir in the mint. Let sit at room temperature for 15 minutes before using.
Recipe courtesy of Bobby Flay