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1
A day before baking the cookies, prepare the fruit: Mix the chopped dried fruit and chopped apple in a bowl, toss with 1/2 cup of the sugar, pour in the vin santo, and stir.
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2
Cover with plastic wrap, and macerate overnight in the refrigerator.
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3
The next day, strain the fruit, catching and reserving the juices in a small saucepan.
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4
Return the fruit to the bowl, and toss with the chopped nuts.
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5
To make the dough: Stir together the flour, the remaining 1/4 cup sugar, and a pinch of salt in a large bowl.
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6
Drizzle in the olive oil, tossing the dry mix with a fork to form coarse crumbs.
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7
Beat the egg with 1 tablespoon water, and pour over the crumbs, tossing and mixing them into a slightly sticky dough.
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8
Wrap the dough in plastic, press it into a small flat block, and let it rest briefly.
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9
Arrange two racks in the oven, and heat it to 375.
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10
Line the baking sheets with parchment paper.
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11
Unwrap the dough, place it between two other pieces of parchment paper, and roll it into a thin rectangular sheet, 12 by 15 inches.
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12
Remove the top parchment, and spread the fruit-nut filling on the dough, leaving a 1-inch margin uncovered on all sides.
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13
Gently pat the filling so it adheres to the dough.
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14
Roll up the dough like a jelly roll, starting at one of the longer sides, into a cylinder or log about 15 inches long.
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15
You can lift the bottom parchment to support the dough sheet as you fold it over into a spiral, enclosing the filling.
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16
When the log is finished, wrap it fully in the parchment paper (so it doesnt stick to the table), and roll it back and forth a few times to make it more compact (and easier to cut).
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17
Unwrap the log, and trim off the ends with the serrated knife.
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18
Next, slice the log crosswise every 1/2 inch or so, into disk-shaped spiral cookies.
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19
(If these begin to crumble as you cut, re-form the log into a compact shape, and start cutting again.)
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20
Lay the cookies flat and spaced apart on the lined baking sheets.
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21
Place the sheets on the two oven racks, and bake for about 15 minutes, then rotate the panstop to bottom rack, and back to frontand bake another 15 minutes or so, until the dough is golden brown and the filling is bubbling.
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22
Meanwhile, heat the reserved fruit juices to the boil in a small saucepan, and cook until syrupy and reduced to about 1/4 cup.
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23
Remove the baking sheets from the oven onto wire racks, and while the cookies are still hot, drizzle the fruit syrup over them.
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24
Let the cookies cool completely.
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25
They will keep for a week or two if well wrapped or in a cookie tin.
