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Step 1
(Note: the pineapple can be marinaded a day in advance, and the entire mixture, minus ice, can be made up to a day ahead of time in order to speed up drink making). Cut the top third of the pineapple off and set it aside. Peel, core, and cut the remaining bottom two thirds of the pineapple into long, thick pieces. The easiest way to do this is to halve the pineapple the long way, then cut the halves again into long thirds or quarters. At this point, it's easy to cut the skin and the tough core off of the pieces. Note that if you do have a preferred method for cutting pineapple, feel free to use it, as long as it yields pieces large enough to grill.
Step 2
Remove the stem and seeds from the cascabel chili. Toast the chili in a hot, dry skillet for about 2 minutes, or until darkened and fragrant, then remove from heat. When the chili is cool enough to handle, chop it into relatively small pieces.
Step 3
Combine the pineapple, chili, lime juice, and grated piloncillo (or brown sugar) in a large bowl or container. Set aside to marinade for at least 2 hours, or overnight.
Step 4
Remove the pineapple pieces from the marinade, but DO NOT discard the marinade. Cut the reserved pineapple top from step 1 into rings (skin on or off, depending on your presentation preference). Preheat an indoor or outdoor grill to a high heat (about 200 C/400 F). Grill the marinaded pineapple for 5-6 minutes, turning a few times to get a little char all around. Grill the reserved pineapple slices for about 2 minutes per side, or just long enough to leave nice grill marks.
Step 5
Place the grilled marinaded pineapple in a blender or food processor along with the leftover marinade. Blend until smooth. This can be kept refrigerated until ready to use. When you're ready to make the drinks, blend the mixture with the ice cubes until smooth. Cut the grilled un-marinaded pineapple into wedges and set aside.
Step 6
(Note this step can be done up to several days in advance) Combine the water and honey in a sauce pan and bring to a gentle boil.
Step 7
Add the hibiscus flowers and reduce to a simmer. Cover and simmer for 15 minutes. Remove from heat, strain out the flowers and refrigerate the liquid and flowers separately (ensure that the liquid has cooled completely before using).
Step 8
If you haven't already done so, blend the pineapple with the ice until smooth.
Step 9
Add 1 oz (30 ml) of mezcal to a martini glass. Pour 2 oz (60 ml) of the pineapple puree over this and mix gently.
Step 10
Mix the hibiscus agua fresca with the remaining 1/2 oz (15 ml) of pineapple puree and pour gently over the drink. It should settle in patches or a spiral in the drink.
Step 11
Garnish with a roasted pineapple wedge and/or pineapple with hibiscus flours. Serve immediately
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