- 1 whole star anise pod
- 1 teaspoon aniseed
- 1 teaspoon coriander seeds
- 1 teaspoon fennel seeds
- 1/4 teaspoon cumin seeds
- 1/4 lemongrass stalk, tough outer layer removed, crushed
- Zest of 1/4 orange, removed with a vegetable peeler
- 1 medium fennel bulb, cored, thinly sliced
- 1 1/2 cups unseasoned rice vinegar
- 1/2 cup sugar
- 2 tablespoons kosher salt
- 2 pounds large heirloom tomatoes (about 3), cut into wedges
- 1 cup cherry tomatoes, preferably heirloom, halved
- 2 tablespoons white balsamic or Sherry vinegar
- 7 tablespoons extra-virgin olive oil, divided
- Kosher salt, freshly ground pepper
- 2 Cubanelle peppers or Anaheim chiles, sliced into 3/4″ rings, seeded
- Fennel fronds (for serving)
- Special equipment: Cheesecloth
- Toast star anise, aniseed, coriander seeds, fennel seeds, and cumin seeds in a small skillet over medium-low heat, stirring often, until fragrant, about 3 minutes. Bundle toasted spices, lemongrass, and orange zest in a piece of cheesecloth and tie with kitchen twine to make a sachet. Place sachet and fennel in a 1-quart jar or bowl.
- Bring vinegar, sugar, salt, and 1/2 cup water to a boil in a medium saucepan, stirring to dissolve sugar and salt. Pour vinegar mixture over sachet and fennel and let cool; discard sachet. Cover fennel and chill at least 12 hours.
- DO AHEAD: Pickled fennel can be made 2 weeks ahead. Keep chilled.
- Combine large and cherry tomatoes, vinegar, and 6 tablespoons oil in a medium bowl; season with salt and pepper. Let sit at room temperature 30 minutes.
- Before serving, heat remaining 1 tablespoon oil in a medium skillet over high heat. Cook Cubanelle peppers, tossing often, until charred in spots, about 4 minutes.
- Serve tomato salad topped with peppers, pickled fennel, and fennel fronds.