Preheat grill to medium.
Trim asparagus approximately 1 1/2 inches from the bottoms. Slightly peel the asparagus from just below the tip to the end. Put into a large bowl and drizzle with olive oil. Season with salt and pepper and toss.
Wrap the ham tightly around each asparagus stalk. Put on the grill and cook the asparagus turning frequently until slightly charred, 2 to 3 minutes. Transfer to a serving platter and serve.