In a medium skillet, heat sugar with water. Heat until it melts and becomes a caramel.
In a medium bowl, mix together the pears and the almonds. Split the vanilla bean lengthwise and scrape the insides into the bowl with the pears, reserving the pod.
Add the orange juice and the vanilla pod to the caramel and bring the mixture to a boil. Add the star anise and reduce for 8 to 10 minutes.
Add the reserved tomato pulp, lemon and orange zests, cinnamon and mint to the bowl with the pears and add 1/4 of the caramel mixture. Stir to blend.
"Stuff" the insides of the tomatoes with the mixture and top with the "hats". Preheat the oven to 350 degrees F.
Place the tomatoes into a baking dish and pour the caramel into the base of the dish.
Place the pan in the oven and cook, basting from time to time, 8 to 10 minutes.
Serve the tomatoes, with the remaining caramel, and vanilla ice cream.