Place the vin santo, sugar, cinnamon, cloves, vanilla bean, and zests in a large, shallow saucepan with 2 cups of water. Bring to a boil, then reduce the heat to low and simmer for 10 minutes.
Peel the pears, leaving the stems intact, and scoop out the seeds from the bottom with an apple corer or melon baller. Lay half the pears on their sides in the poaching liquid and simmer for 20 minutes, carefully turning the pears once with a spoon. Remove with a slotted spoon. Poach the remaining pears in the same liquid. Snip off the hard stems from the figs with scissors. Add the figs, apricots, prunes, and the first batch of poached pears and simmer 5 to 10 more minutes, until the pears and the dried fruit are all tender.
Chill the pears, dried fruit, zests, and poaching liquid. Remove the cinnamon, cloves, and vanilla bean before serving if you like.
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