Soak the skewers
If using bamboo skewers, place them in water for at least 20 minutes so they do not burn too quickly on the grill.
Prep the vegetables and pineapple
Cut the pineapple, zucchini, yellow squash, red onion, and bell pepper into sturdy pieces. Leave cherry tomatoes whole.
Heat the grill
Preheat the grill to medium heat and lightly oil the grates to help prevent sticking.
Thread the skewers
Add the vegetables and pineapple to the skewers, alternating colors and textures so each skewer has a good mix.
Make the marinade
In a small bowl, whisk together olive oil, dried basil, dried oregano, salt, and black pepper.
Brush the skewers
Brush the herb oil mixture over the prepared skewers, coating the vegetables and pineapple on all sides.
Grill until tender
Place the skewers on the grill and cook for 10 to 15 minutes, turning occasionally. Brush with extra marinade as they cook.
Serve warm
Remove from the grill once the vegetables are tender and lightly charred. Serve right away.