01 -
If using fresh octopus, freeze for 2-3 days to tenderize, then thaw completely. Place octopus in a large pot without cleaning.
02 -
Add enough water to almost cover octopus. Add vinegar, lemon slices, and optional seasonings (bay leaves, thyme, garlic). Bring to a boil, then simmer for 40-50 minutes for 1kg octopus, or up to 1 hour for larger specimens.
03 -
Insert a knife through the thickest part of a tentacle. The meat should feel tender but not mushy. Do not overcook or the skin will start peeling off.
04 -
Remove octopus from pot and let cool. Separate head from tentacles. Slice open head, remove inner membranes and rinse if sandy. Cut head into quarters. Remove teeth from center base of tentacles.
05 -
Cut tentacles separately for easier grilling. Pat octopus completely dry with paper towels. Brush all pieces with 1 tablespoon olive oil.
06 -
Heat grill or grill pan over high heat. Brush grates with oil. Add octopus and reduce heat to medium-high. Grill for 10-12 minutes, turning tentacles every 2-3 minutes to char evenly on all sides.
07 -
Whisk remaining olive oil with lemon juice. Arrange grilled octopus on serving plate, drizzle with ladolemono, and sprinkle with oregano, salt, and pepper.