Place heavy cream and vanilla extract in a bowl of a stand mixer fitted with the whisk attachment. Whisk on medium-high until stiff peaks form. Set aside.
Place mascarpone cheese and granulated sugar in a bowl of a stand mixer fitted with the paddle attachment and mix on medium speed until just combined. Fold in whipped heavy cream and mix for a few seconds until incorporated and smooth.
Place pitted and halved (or quartered) cherries, sugar, cinnamon and brandy in a small saucepan and bring to a simmer. Add water and simmer for 5-6 minutes.
Transfer mixture to a sieve, draining liquid into a wide bowl or plate (wide enough to fit the length of a ladyfinger). Place cherries in a separate glass bowl and allow to cool completely.
Dip both sides of each ladyfinger (one by one) quickly into cherry syrup mixture (do not soak as ladyfingers will become soggy).
Place dipped ladyfingers side by side (you will have 2 rows) at the bottom of an 8x8" glass baking dish (or use a brownie pan lined with parchment paper). You may need to cut off part of the ladyfingers for the "shorter" row.
Spread half of the mascarpone-cream mixture on top of the bottom row. Use a spatula or palette knife to smooth out the surface. Spread all cherries evenly on top of the mascarpone layer.
Repeat the last three steps to create a second row of lady fingers and mascarpone covering (do not put cherries on the top layer). Cover and refrigerate for 4-5 hours up to overnight.
Before serving, sprinkle dark chocolate shavings over tiramisu.