Preheat your sous vide to 75°C.
Bring a large pot of water to a rolling boil. Dip each octopus tentacle into the boiling water for no longer than 30 seconds. This helps the tentacles curl and improves presentation.
Transfer the octopus to sous vide bags. Add olive oil, salt, peppercorns, and bay leaves. Seal the bags.
Cook in the sous vide for 5 hours until completely tender.
Remove the octopus from the bags and immediately transfer to an ice bath. Allow to cool fully, then refrigerate for at least 8 hours or overnight. This helps firm it up for grilling.
To make the dressing, whisk together olive oil, orange juice, lime juice, honey, and Aleppo pepper flakes. Season to taste.
Arrange the sliced citrus and radish on a platter. Drizzle lightly with the dressing and set aside.
Heat a grill or grill pan over medium-high heat. Toss the chilled octopus in a little olive oil.
Grill the octopus on both sides until nicely charred and crispy, about 7 to 8 minutes per side, depending on thickness.
Slice the octopus, place over the citrus salad, drizzle with remaining dressing, and finish with fresh herbs.