I follow the preparation technique in the Babbo cookbook. You simply simmer the Octopus in water and a tablespoon or two of red wine vinegar until it is fork tender, about an hour for a one pound octopus. (It also recommends placing a wine cork in the pot. I usually do this, mostly because I have a ton of corks lying around, but I'm not sure that its necessary). Cooking the Octopus like this breaks down the fibers and gelatin. Since Octopi have no skeletal system to support them their muscle fibers are very tough.
It can be served right out of the pot or chilled and served cold. It can also be quickly grilled, broiled or pan seared after being chilled to achieve some color and texture on the outside while maintaining a tender interior.
I grilled the Octopus, giving it a nice char and a rich smokey flavor. I sauteed some sliced cipollini onions with green zebra and kellog breakfast tomatoes and made a vinaigrette with the tomato juice and pulp. I slow-cooked whole garlic cloves in olive oil, making them smooth and sweet. Underneath the salad is some caramelized fairytale eggplant. And on top some fire roasted hot peppers.