01 -
If the octopus is frozen, thaw in the refrigerator overnight. Place the octopus, lemon slices, and red wine vinegar in a medium pot. Add 2 1/2 to 3 cups water to nearly cover the octopus. Bring to a boil over high heat, then reduce to low and cover. Simmer for 40–50 minutes, or until the thickest part of a tentacle is tender when pierced with a knife. Do not overcook.
02 -
Transfer the cooked octopus from the pot and let cool to room temperature on a plate.
03 -
Once cooled, separate the tentacles from the body using a sharp knife. Remove and discard the hard central piece containing the octopus' beak. Open the head and rinse thoroughly under cool water to remove any sand or residue.
04 -
Preheat the grill or grill pan on high. Lightly brush the grates and octopus with extra virgin olive oil. Grill octopus tentacles for 10–12 minutes, turning every 2–3 minutes, until charred on all sides and the skin is firm.
05 -
Combine 5 tablespoons extra virgin olive oil with 3 tablespoons lemon juice in a small bowl; whisk until emulsified.
06 -
Arrange grilled octopus on a serving plate. Drizzle with the ladolemono dressing, sprinkle with dried oregano, and serve with lemon wedges.