Adjust oven rack to middle position and heat to 300°F. Spray loaf pan with cooking spray, making sure to spray all edges. Set aside.
Spread fennel seeds onto a sheet pan and transfer to oven for 10 minutes until lightly toasted and fragrant.
Remove fennel seeds from oven and transfer to a small bowl to cool. Once cooled, measure out 1 tablespoon and set aside. Transfer remaining seeds to a spice grinder and process until finely ground. Measure out 2 teaspoons of ground fennel, save remaining for another use.
In a medium bowl whisk together eggs, sugar and vanilla until pale in color. Set aside.
Lightly squeeze juice from shredded pear, reserving 2 tablespoons. Measure out one packed cup shredded pear and transfer to a small bowl. Add 2 tablespoons reserved pear juice, ¼ teaspoon orange zest, 2 tablespoons orange juice, and cranberries, mix to combine.
Add buttermilk, oil, fennel seeds and ground fennel to pear mixture. Mix until combined.
In a large bowl whisk together flour, baking powder, baking soda and salt. Form a well in the dry ingredients and add wet ingredients. Fold together until just combined and no flour pockets remain.
Pour batter into loaf pan and spread evenly. Sprinkle top with turbinado sugar and transfer to oven.
Bake for 55–60 minutes or until toothpick comes out clean.
Cool bread in pan on wire rack for 10 minutes, then remove loaf from pan and continue to cool on wire rack. Serve warm or at room temperature.