Grilled Baby Octopus with Tomato Confit, Potatoes & Chard

Grilled Baby Octopus with Tomato Confit, Potatoes & ChardSending my boyfriend to the fish market is a lot like sending a kid into a candy shop. Only difference is, Matt’s got an adult appetite and his own credit card.  Allow him into the store and he’ll inevitably buy twice as much of whatever he originally went in for plus at least one grab-bag item.

Which is how I came to have a frozen brick of baby octopuses in my freezer.

I try to act annoyed, but truthfully, I’d be troubled if he actually returned from shopping with 2 respectably sized 6 oz. fillets of fish and nothing more.  It’s who he is and what he does. And I’m left to figure out what to do with everything.

Which is who I am and what I do.

I decided on grilling the octopuses (yes, octopuses seems to be the correct plural of octopus) and pairing them with slow-roasted tomatoes, Swiss chard, and the world’s tiniest fingerling potatoes from the farmer’s market.  I’ll be honest, this recipe is a fair amount of work compared to the kind of summer cooking I’ve been up to lately (see 10 minute steak with grilled corn relish or super quick raspberry-plum coffee cake), but all the steps are easy and you could certainly do a few of them a day ahead.

We start with the tomatoes.  Peel a half-dozen Roma tomato, quarter and seed them, and place in a small baking dish or pie plate.  Tuck in sprigs of thyme or rosemary and a few smashed garlic cloves.  Sprinkle with salt and pepper then douse with olive oil.  Bake the tomatoes low and slow until they’re soft and sweet. Tomato Confit

Next we’ll boil the octopuses.  I tossed a few peppercorns, bay leaves, and half a lemon in the pot.  Also, a wine cork to help tenderize.  Why?  Because Mario Batali told me to and, presumably, some old Italian woman who has lived by the seashore for 90 years told him to.  I’m not going to mess with that. Baby Octopi

Simmer ’til they’re tender and they’ve turned all sorts of beautiful shades of purple.  Cooked OctopusWe’re getting there!

Boil the potatoes and blanch the chard.  Smash a few of the tomato pieces and garlic cloves with a spoonful of honey and a splash of vinegar.  Coat the octopuses in the mixture before they hit the grill.   Toss the potatoes and chard with the remaining tomatoes. Potatoes, Swiss Chard & Roasted Tomatoes

Pull the octopuses off the grill when they’re warm through and charred here and there.  Put it all together and we’re done–dinner’s ready.  The bf got to feel like a kid in a candy shop and I got to learn how to cook something new.  That’s good stuff.Grilled Octopus with Roasted Tomatoes, Potatoes & Chard

Grilled Baby Octopus with Tomato Confit, Potatoes & Chard
Prep time
Cook time
Total time
Recipe type: Dinner, Entree, Fish, Seafood
Cuisine: American, Italian
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.



  1. says

    ha! if I send my hubby to the store I’m lucky to end up with anything resembling what I asked for 😛 That’s okay, I do all of our shopping.

    I picked up these frozen blocks of baby octopus(es) before, too – I usually just unthaw and cut them up, then marinade and cook just as I would squid – I’ll have to try your recipe next time. The cork is an intriguing idea 🙂

  2. pam says

    They look so PRETTY!! I remember the first time I had them – in Italy- after a few glasses of wine they went down easy! Now I love them! The whole dish looks beautiful and delicious. And I love the cork story! That reminds me of another Italian old woman story! Can’t argue with old wives’ tales from the old country!

    • says

      They’re much prettier after they’re cooked–the colors pop and the tentacles curl at the ends. And I bet the old woman we’re both thinking of could definitely shed some light on the cork situation if she was still around 😉

  3. says

    Looking forward to trying this tonight, and will comment accordingly. Must admit I was a little confused about the cork until I read the fine print. lol. First I thought of a funny story we have here in Australia about cooking one of our native birds – yes, nothing is off the table in Australia, we even eat the animals that feature on our coat of arms – anyway, the story goes about cooking a Galah; put the Galah in a pot of boiling water with a rock, when the rock is soft, throw away the Galah and eat the rock (Galah meat is very, very tough) – thought it might have been the same for the baby octopus and the cork – lol – sorry.

  4. says

    WOW! My goodness, such a tasty dish. The tomato/garlic/rosemary/thyme and olive oil combination is so delicious. The baby octopus being double cooked came out just amazing. Once the greens are mixed with the tomatoes and potatoes, wow ….
    Thank you for such an amazing dinner.

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