Make brine/simmer liquid: in a large pot combine 8 cups water, kosher salt, white wine vinegar, bay leaves, peppercorns and crushed garlic. Bring to a gentle simmer over medium heat.

Tenderize and poach the octopus: when the liquid is simmering (not vigorously boiling), lower the heat to maintain a gentle simmer. Submerge the octopus (you may need to coil the tentacles); cover partially. Simmer gently until the thickest part of a tentacle is tender when pierced with a skewer, about 35–50 minutes depending on size (for a 2 lb octopus expect ~40 minutes). Turn the octopus once during cooking to ensure even heat.

Test for doneness: insert a skewer into the thickest area — it should meet little resistance but not fall apart. Overcooking makes it mushy; undercooking is tough. When done, remove octopus from the poaching liquid and let cool slightly on a tray until manageable.

Marinade & Finish

Prepare marinade

In a bowl whisk together 1/2 cup extra-virgin olive oil, lemon juice, lemon zest, minced garlic, smoked paprika, red pepper flakes, chopped oregano, sea salt and black pepper until emulsified. Reserve 3 tablespoons of the marinade for finishing.

Marinate octopus: while still slightly warm, cut the octopus into grilling portions — separate tentacles and if desired halved body into 1–2 pieces. Place pieces in a shallow dish, pour most of the marinade over them and turn to coat. Let sit at room temperature for 15–20 minutes (or refrigerate up to 1 hour).

Preheat hearth grill: prepare a hot-fire hearth grill or a very hot charcoal or gas grill. You want a two-zone fire if possible: a very hot direct-heat side for quick searing and a slightly cooler side to finish. Clean and oil grates well.

Grill the octopus: when the grill is hot (grates shimmering), remove octopus from marinade letting excess drip off. Place tentacles first on the direct hot side. Grill 1–2 minutes per side, until you get a good char and caramelization — rotate to get cross-hatch marks. Move to the cooler side if pieces need another minute to cook through without burning. Brush occasionally with reserved marinade while grilling.

Finish and rest: transfer grilled octopus to a platter. Drizzle with the reserved 3 tablespoons marinade or 2 tsp olive oil, sprinkle chopped parsley and microgreens if using. Season to taste with a little extra sea salt and black pepper. Let rest 3–5 minutes before serving so juices settle.

For Serving

Slice larger tentacles diagonally into bite-size pieces or serve whole small tentacles. Arrange on a warm platter with lemon wedges alongside. Optionally drizzle a touch more olive oil and scatter extra parsley or microgreens for color.

Serve: recommended to serve immediately while warm. Pair with charred bread or a simple salad and a bright white wine or chilled rosé.