Prep time: 2 hours, including refrigeration time for chicken (some overlap with cook time)
Cook time: 30 minutes
1 large whole pineapple
3 boneless, skinless chicken breasts
Salt and ground black pepper
1/2 small red onion, diced
1 jalapeño, seeds removed, diced
2 avocados, pitted and chopped
Juice of 1 lime
1 tablespoon chopped fresh cilantro
Carefully cut off the top and bottom of the pineapple. These can be discarded. Stand the pineapple upright. Cut the skin off the pineapple, removing it in 6 long strips. To do this, begin cutting at the top of the fruit and slice downward, letting the knife follow the curve of the fruit. Leave about 1/2 inch of flesh on each strip of skin. Rotate the fruit and repeat. Set strips of pineapple skin aside while you prepare the chicken. Reserve the skinned fruit.
Place each chicken breast between sheets of plastic wrap and use a meat mallet or rolling pin to pound to an even 1/2-inch thickness. Season each on both sides with salt, pepper, cumin and cayenne.
Lay each piece of chicken over the cut side of one of the slices of pineapple skin. Set a second strip of pineapple skin, cut side down, on top. Use kitchen twine to tie the bundles to hold them together. Refrigerate the chicken bundles for about 30 minutes.
When ready to cook, heat one side of the grill to high, the other side to low.
Meanwhile, cut the skinned pineapple (the flesh) into thick rounds. Use a small round cookie or biscuit cutter (or a paring knife) to cut out and discard the core from each round.
When the grill is hot, arrange the chicken bundles on the cooler side of the grill. Cook for 15 minutes per side, or until the chicken reaches 165 degrees at the center. During the final 10 minutes, add the pineapple rings and cook for 5 minutes per side.
While the chicken cooks, prepare the guacamole. In a bowl combine the red onion, jalapeño, avocados, lime juice and cilantro. Gently mix; season with salt and pepper.
To serve, place one chicken bundle on each plate. Set a grilled pineapple ring next to it, then spoon some of the guacamole into the center of and over the pineapple ring.
Per serving: 430 calories; 190 calories from fat (44 percent of total calories); 21 g fat (3.5 g sat.; 0 g trans); 70 mg cholesterol; 35 g carbohydrate; 31 g protein; 12 g fiber; 280 mg sodium.