If using bamboo skewers, place them in water to soak for at least 30 minutes to prevent burning on the grill. While skewers soak, prepare your marinade by whisking together the olive oil, balsamic vinegar, dried basil, dried oregano, garlic powder, kosher salt, and black pepper in a bowl until well combined. This allows the dried herbs to begin blooming in the oil, which intensifies their flavor.

While the skewers soak and marinade develops, cut all produce into appropriate sizes: peel and cube the pineapple into 1.5-inch pieces, slice zucchini and yellow squash into 1-inch thick rounds, quarter the red onion into 1-inch wedges, halve the large mushrooms if needed for even cooking, leave cherry tomatoes whole, and chunk the bell peppers into 1.5-inch pieces. Keep similar vegetables grouped together to make assembly easier and faster.

Remove skewers from water and pat dry. Thread the prepared vegetables and pineapple onto the skewers in an alternating pattern—this creates visual appeal and ensures even cooking as different vegetables cook at slightly different rates. I like to start and end each skewer with a piece of bell pepper or onion, as they're sturdier and help hold everything together. Aim to pack the skewers snugly but not so tight that pieces can't cook evenly.

Preheat your grill to medium heat (around 375-400°F if using a gas grill). Once hot, use a brush or oiled paper towel to thoroughly oil the grates, which prevents sticking and helps create those beautiful char marks. Let the grate heat for another minute after oiling.

Generously brush the assembled skewers with the marinade from Step 1, coating all sides well. Place skewers directly on the oiled grates and grill for 10-15 minutes, turning them every 2-3 minutes to ensure even cooking and prevent any single side from charring too quickly. Brush with additional marinade each time you turn the skewers. I find that medium heat and frequent turning produces the best results—tender vegetables with light caramelization rather than heavy charring.

Once the vegetables are tender and lightly charred on the edges, remove skewers from the grill and let them rest for 2-3 minutes before serving. This allows the vegetables to settle and makes them easier to eat. Transfer to a serving platter and serve warm.