Cut butter into small pieces and add to flour mixture.
Cut butter into flour with a pastry cutter or forks until butter chunks are pea-sized.
Add in egg yolks and vanilla extract and knead with your fingers until combined. If dough is dry and crumbly, add ice water a teaspoon at a time until dough holds together when gently squeezed.
Form dough into a disk and wrap in plastic wrap, wax paper or freezer paper.
Refrigerate for at least 1 hour.
Cut dough into 8 equal parts.
Roll each piece between two pieces wax paper or plastic wrap.
Place in tart pan and press into the bottom with sides rolling over pan edges.
Run the rolling pin over the pan to cut off excess dough.
Repeat with remaining dough.
Chill for 30-60 minutes.
Preheat oven to 350F.
Line chilled crusts with foil (shiny side up) and fill with dried beans or rice.
Bake for 25 minutes and then remove foil and beans.
Bake for another 15-25 minutes or until crust is golden and set.
Let cool for 15 minutes and then remove crusts from tart pans.
Pineapple filling
In a medium sauce pan combine rum, sugar, vanilla bean and butter and bring to a gentle boil.
Once the sugar has melted, poach pineapple slices in small batches for 7-10 minutes, or until golden brown but not falling apart.
Remove pineapple and place on a cooling rack placed over cookie sheet.
Once all pineapple is poached, return any liquid that has drained off the pineapple to the pan.
Reduce the poaching liquid until it is thick and syrupy and set aside.
Place pineapple in an airtight container and refrigerate until ready to assemble tarts.
Pastry Cream
In a small bowl combine egg yolks and brown sugar and whisk to combine.
In a medium sauce pan combine cornstarch, milk and heavy cream and whisk to combine.
Place over medium heat and bring to a gentle boils while whisking constantly.
Once the mixture starts to thicken, temper the eggs by adding a half cup of the milk mixture to the eggs and whisk.
Now add the egg mixture to the pot and cook until thick and smooth (while constantly whisking).
Add in reserved syrup and whisk until it incorporates.
Remove from heat and strain through a fine mesh sieve into a bowl.
Add butter and whisk until butter is melted and the pastry cream is glossy.
Let cool on the counter for about 20-30 minutes, whisking every few minutes to keep the custard from forming a skin.
Cover with plastic wrap and refrigerate until chilled.
Assembly
Line each tart shell with a thin layer of pastry creme.
Fill with pineapple slices, arranging them in layers to make a flower pattern.
Add a cherry to the center and a dollop of whipped cream.
Drizzle leftover poaching syrup and pastry creme over tartlets and sprinkle with powdered sugar.
Notes
These work best as tartlets. The first time I baked a whole tart and it was difficult to cut and turned into a sloppy mess! We used tart pans similar to these.