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Heat oven to 425 degrees F.
Wind bacon around each date, securing it with a toothpick and arranging it on a rimmed, foil-lined baking sheet or roasting dish.
Combine cider vinegar, maple syrup, and pepper flakes in a small bowl. Brush or spoon over each bacon-wrapped date; you can even very briefly roll them in the mixture to coat. Sprinkle with sea salt.
Roast for as little as 15 and up to 35 minutes, until bacon is a deep, crisp, sizzling brown — this varies a lot between brands.
Check in on the early end, and then every 5 minutes thereafter, to get the color and crisp just right. If you have extra vinegar mixture, you can brush it on again in the second half of the baking time.
Serve warm, sprinkling with more sea salt and/or pepper flakes to taste.