Grilled Baby Octopus with Tomato Confit, Potatoes & Chard
Recipe type: Dinner, Entree, Fish, Seafood
Cuisine: American, Italian
Prep time: 
Cook time: 
Total time: 
Serves: 3 as main, 6 as appetizer
  • 6 Roma Tomatoes
  • 4 cloves Garlic, smashed
  • 3 sprigs Thyme
  • 1 sprig Rosemary
  • Extra Virgin Olive Oil
  • 1½ # Baby Octopuses, cleaned
  • ½ Lemon
  • 4 cloves Garlic
  • 2 Bay Leaves
  • ½ tsp. Black Peppercorns
  • 1 Cork
  • 1 # Tiny Fingerling Potatoes (or cut in bite-sized pieces)
  • 1 large bunch Swiss Chard, tough center stalks removed
  • 1 Tbsp. Honey
  • White Wine Vinegar
  1. Preheat oven to 250°.
  2. Score in X through the skin of each tomato. Drop them into a small saucepan of boiling water for 10-15 seconds until the skin loosens and you can easily peel the tomatoes. Cut in quarters and remove the seeds. Place the tomato segments in a small baking dish or pie pan. Sprinkle with salt and pepper, tuck in the thyme, rosemary, and garlic and cover with about a ¼ c. olive oil. Place in oven and bake for about 2 hours until the tomatoes are soft and juicy, the flavors concentrated. Can be made 1 or several days in advance.
  3. Meanwhile, simmer the octopuses with lemon, garlic, bay leaves, peppercorns, and cork until tender when pierced with a knife, 45 minutes-1 hour. Drain and remove flavorings and cork. Can be done hours or 1 day in advance.
  4. Smash about a ⅓ of the roasted tomatoes using a mortar and pestle or pulse in a food processor. Combine with about 2 Tbsp. of the tomato-y olive oil, 1 Tbsp. honey, 1 Tbsp. white wine vinegar, salt, and pepper. Pour over the boiled octopi.
  5. Meanwhile, boil the potatoes until tender and blanch the chard in salted water.
  6. Light a grill or heat a grill pan (this is what I did, as the weather got nasty at the last-minute). Grill the octopuses 3-4 minutes per side until lightly charred.
  7. Chop the chard and the remaining tomatoes. Combine with the potatoes and toss with the remaining tomato-oil and vinegar, salt, and pepper to taste. Divide between plates and top with the grilled octopuses.
Recipe by strawberryplum at