1-pound medium-sized squid, tentacles included, cleaned
Extra-virgin olive oil
Salt and freshly ground pepper
1 loaf day-old Italian bread, cut into 1-inch thick slices
2 ripe beefsteak tomatoes, cut into 1/2-inch thick slices
1/4 cup chopped fresh Italian parsley leaves
Smoked Chile Vinaigrette, recipe follows
1/4 cup fresh mint leaves, torn
Red wine vinegar, for drizzling, optional

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.

Smoked Chile-Mint Vinaigrette:
1/3 cup red wine vinegar
1 tablespoon Dijon mustard
1 tablespoon pureed chipotle peppers in adobo sauce
1 tablespoon honey
2 cloves garlic, finely chopped
Salt and freshly ground pepper
3/4 cup olive oil or canola oil
2 tablespoons finely chopped fresh mint leaves
 
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.