Combine Florida orange juice, white wine, white wine vinegar, carrot, onion, celery, bay leaf and peppercorns in large pot. Bring to simmer and cook for 10 minutes. Add octopus and cook for 1½ hours. Remove octopus from cooking liquid and toss with olive oil. Reserve.
While octopus is cooking, prepare Pequillo Pepper Vinaigrette: Combine ¼ cup Florida orange juice, 2 Tbsp Florida orange zest, ½ cup pequillo peppers and 2 Tbsp sherry vinegar in blender. Blend until smooth and slowly drizzle in 2 Tbsp olive oil. Season with salt and pepper, to taste. Reserve.
For Purple Potato Salad, combine 3 cups purple potatoes, 2 Tbsp olive oil, 1 Tbsp sherry vinegar and 3 Tbsp chives. Season with salt and pepper to taste.
Grill octopus over medium-high grill until charred and crispy. Serve over Purple Potato Salad and drizzle with Pequillo Pepper Vinaigrette.