To begin, tenderize the octopus by simmering it. In a large pot, add the octopus and cover with water. Bring to a gentle simmer over low heat, and cook for 45-60 minutes until the octopus is tender. Test by piercing with a fork; it should slide in easily. Remove the octopus and let it cool slightly, then pat dry with paper towels.
While the octopus cools, prepare the marinade. In a large bowl, whisk together the olive oil, lemon juice, minced garlic, oregano, and black pepper. This marinade will infuse the octopus with traditional Greek flavours.
Cut the octopus into serving sized pieces, typically by separating each tentacle and dividing the body into manageable sections. Place the pieces in the marinade, ensuring each piece is well coated. Cover and let marinate for at least 30 minutes, or up to 2 hours for a more intense flavour.
Preheat your grill to medium-high heat (about 200°C/400°F). If you are using an outdoor charcoal grill, wait until the coals are ashed over for a more even, flavourful char.
Once the grill is hot, place the marinated octopus pieces directly on the grill grates. Grill for 3-4 minutes on each side, or until lightly charred with grill marks. Baste with the remaining marinade as you grill to keep the octopus moist and to enhance its flavour.
As the octopus grills, keep an eye on it to avoid overcooking. Octopus can become rubbery if left on the grill too long, so once it develops a good char and heated through, it’s ready.
Once done, remove the octopus from the grill and let it rest for a few minutes. This brief resting time helps the juices settle, making the octopus more flavourful and tender.
To serve, arrange the grilled octopus on a platter. Garnish with fresh parsley and serve with extra lemon wedges on the side. Pair with crusty bread or a traditional Greek salad. Drizzle with additional olive oil, if desired, for a more luxurious finish.