Start by soaking the bamboo skewers in water for at least 30 minutes to prevent them from charring on the grill. While they soak, prepare all your vegetables and fruit: core and cut the pineapple into 1-inch chunks, slice the zucchini and yellow squash into 1/2-inch thick rounds, leave the baby bella mushrooms whole, cut the red onion into 1-inch wedges, keep the cherry tomatoes whole, and cut the red bell pepper into 1-inch squares. Having everything prepped and ready before you start skewering makes the assembly much faster and more organized.

In a bowl, whisk together the extra virgin olive oil, balsamic vinegar, dried basil, dried oregano, garlic powder, salt, and black pepper until well combined. I like to let this mixture sit for a few minutes so the dried herbs can bloom and release their flavors into the oil—it makes a noticeable difference in the final taste.

Remove the soaked skewers from water and begin threading the prepared vegetables and pineapple onto each skewer, alternating between different items to create a colorful, balanced arrangement. Distribute the ingredients evenly among all skewers so they cook at the same rate. Thread them snugly together but not so tight that they're crushed—you want them to cook evenly and develop nice color on all sides.

Heat your grill to medium heat (around 375-400°F if using a gas grill, or medium coals for charcoal). Once the grill is hot, lightly oil the grate with a folded paper towel dipped in oil to prevent sticking. Brush all sides of each loaded skewer generously with the herb oil marinade from Step 2, making sure to coat the vegetables thoroughly.

Place the skewers directly on the grill grate and cook for 10 to 15 minutes, turning them every 2 to 3 minutes to ensure even cooking and prevent burning. Each time you turn the skewers, brush them again with the remaining herb oil marinade—this keeps them moist and builds flavor. The vegetables should be tender and have light char marks when done. I find that turning frequently helps the vegetables caramelize without getting too charred, and the basting keeps everything juicy.

Remove the skewers from the grill and let them rest for 2 to 3 minutes before serving. This brief rest allows the vegetables to relax and helps them stay tender when you handle or eat them. Serve warm as a main dish or appetizer.