Grilled Octopus with Butternut Squash

Instructions

1. 1

   Bring a large pot of salted water to a boil and add the octopus. Reduce heat to a simmer and cook for 35-40 minutes until the octopus is tender. Drain and let cool slightly, then pat dry with paper towels.

   Tip: The octopus is done when a knife easily pierces the thickest part of the tentacles. This pre-cooking ensures tender, succulent flesh before grilling.

2. 2

   While the octopus cooks, toss the butternut squash wedges with 2 tablespoons of olive oil, half the salt, and black pepper. Arrange on a baking sheet and roast at 400°F for 25-30 minutes until golden and caramelized, stirring halfway through.

   Tip: Roasting the squash until it develops caramelized edges adds depth and sweetness that complements the tender octopus.

3. 3

   Heat 3 tablespoons of olive oil in a small saucepan over low heat. Add minced garlic and sage leaves, infusing for 5-7 minutes until fragrant and the sage is crispy. Strain out solids and set the garlic oil aside.

   Tip: Keep the heat low to gently infuse the oil without burning the garlic, which would turn bitter.

4. 4

   Preheat a grill or grill pan to medium-high heat. Brush the cooled octopus tentacles lightly with the remaining olive oil and season with the remaining salt and red pepper flakes.

   Tip: Lightly oiling the octopus prevents sticking and helps achieve those beautiful charred marks.

5. 5

   Grill the octopus tentacles for 2-3 minutes per side until deeply charred and marked. Transfer to a cutting board and cut into 2-inch pieces.

   Tip: Don't move the octopus around too much on the grill—let it sit to develop color and crust for maximum flavor.

6. 6

   In a small bowl, whisk together the lemon juice and remaining 1 tablespoon of olive oil to create a bright vinaigrette. Season with a pinch of salt and pepper.

   Tip: This simple vinaigrette brightens all the rich flavors and adds acidity that's essential for balance.

7. 7

   Arrange roasted butternut squash wedges on a serving platter, top with charred octopus pieces, then drizzle generously with the garlic-sage oil and lemon vinaigrette. Garnish with fresh parsley and crispy sage leaves.

   Tip: Plate just before serving so the octopus and squash are still warm and the sage remains crispy.