Pour the wine and add the cinnamon sticks (or ground cinnamon) to a small sauce pan and cook over med-high heat until the liquid is more than ¾ reduced. This will take about 15 minutes. Turn off the heat and discard the cinnamon sticks.
In a traditional tarte tatin mold (as shown in the video) or 10-12 inch skillet (oven-proof), combine the sugar and water. Caramelize the sugar, stirring regularly over med heat until a med brown/amber color is seen. Be patient, stirring occasionally and checking often. This will take about 15 minutes. Remove from the heat.
Add to the caramelized sugar the reduced red wine syrup as well as the butter and liqueur (optional, but a delicious idea if you do ;)). Cook for about one minute to combine and loosen any caramel that has hardened - stirring to do so.
Having prepared the pear halves already (while the sugar is caramelizing), add the pear halves to the skillet (8-12). You will turn them as you cook them over the 15-20 minutes but when they are finished cooking, arrange them in the skillet as you choose based on what you want to see when you present. Remember the bottom of the skillet will be what is seen. The pears should be tender at this point and the pan juices are syrupy. Turn off the heat and let cool for about 20-30 minutes so that your pastry won't melt (so to speak) when placed on top of the pears.
Preheat the oven to 375 F (190 Celsius).
Take out the pastry dough from the fridge and roll out so that about 2” of pastry will fall over the side of the skillet when placed atop.
Place the pastry on top of the pears in the skillet, tucking the edges overhanging into the inside of the skillet to create an edge, patching if any holes appear. This does not have to be neat remember because is the bottom of the dish as it will be flipped before serving.
Bake for about 50 minutes to 1 hour or until deep golden brown. Before you let it cool, run the back of a knife around the interior edge of the pan. Let the tart cool in the skillet for only about 5 minutes before flipping it. Carefully remove do so by placing a large plate or platter on the top of the skillet and over a counter to catch any drips. Let cool further for 10-15 minutes before serving.
Serve warm with gelato or Chantilly cream and of course a hot cuppa!