Boil the potatoes. Prick the potatoes on all sides with the tines of a fork 1/8-1/4" into the flesh. In a large pot add water and a pinch of salt, stir to dissolve then add the potatoes. Bring to a boil and cook until fork tender, about 10-12 minutes. Strain in a colander and place it back over the warm pot to dry the skin of the potatoes. When cool, cut smaller potatoes in half and the others to around the same size, so that they are bite-sized.
Prepare the vegetables for the grill. Cut the carrots into halves equal in length. Then cut the smaller tip of the carrot into fourths lengthwise and the larger half into sixths or eighths. The key is making the spears all the about the same size. Line up these and all the vegetables on a tray along with the pineapple slices and drizzle with olive oil. Sprinkle all with a pinch or two of salt and a few grinds of pepper. Flip the pineapple rings and lettuce halves. Repeat the drizzle of oil and seasoning with salt and pepper for them only. Roll and jiggle the rest to fully coat them.
Grill the salad. Heat the grill or grill pan to medium high. Excluding the lettuce halves, place vegetables and fruit directly on the grill. Use tongs to tend to the grill. Roll and flip the vegetables until your personal preference for doneness, pulling each off to a tray when done. The carrots and potatoes are best when charred, caramelized, and a bit crispy on the ends, about 10 minutes. Corn is great fresh, so just go for color on all sides, about 8 minutes total. Asparagus are best when charred and maintaining a bit of a snap, about 6 minutes. The bell peppers and pineapples are best when slightly charred, but still juicy, about 6 minutes total. Lastly, Grill the lettuce, starting with the flat side down first. Grill until slightly wilted and charred on both sides, 5-6 minutes total. Remove each to a serving plate, flat side facing up. When the grilled goods are all cool enough to handle, roughly chop the pineapple rings and trim the kernels off the corn. Add both to a large bowl along with the rest.
Make the vinaigrette. In a medium bowl add pineapple juice, mustard, apple cider vinegar, sugar, liquid smoke and whisk until combined. Continue to whisk rigorously while slowly pouring the olive oil into the bowl with your other hand or with the help of a friend, nice to have them in the kitchen! Taste the vinaigrette and season with a pinch of salt and few grinds of black pepper.
Dress the salad. Pour over the bowl then gently toss using tongs. Evenly pile tossed salad on top of lettuce halves on each plate and drizzle the remaining dressing, if any over the top.
Preparation time: 25 minutes
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