Preheat oven to 350
Heat oil in a pan. Sear apples until caramelized.
Whisk eggs in a mixing bowl. Add in sugar, then cream, maple, vanilla, and cinnamon
Spray a casserole dish or deep pan with pan spray. Pour a coating of the egg and cream mix (called a royale) into the pan. Then, lay slices of bread in the pan to cover the bottom. If the pan is too big, cut some of the bread to make sure it covers the whole bottom of the pan. Next: spread apple and cherry slices evenly on top of bread. Top with egg mix. Repeat this layering of bread, fruit, and "royale" mix 2 times, so you have 3 layers of bread. There should be enough mix. If it is too dry, make a little more. It should be very moist (like bread pudding). The bread soaks up a lot of moisture.
Bake for 40 minutes. It should be solid, not wiggly. check the center to make sure it is not liquid. If it needs more time, let it bake longer. Be careful, though, not to get the top too dark. If it is not fully cooked through, but the top is brown. Cover with foil, and finish.
While the strata is baking or before you make it, toss sliced berries with sugar, juice, and booze. Allow to macerate in the fridge until service time. This can be done up to 1 day in advance. But, try to do it day of. Otherwise the berries start to look like frozen. If they maintain their fresh appearance, they are a better visual and textual experience.
Make the whipped cream: Using either a mixer or a hand whisk: whip the cream in a stainless steel bowl until it starts to become thick. When it begins thickening, add in the sugar and vanilla. Don't over-whip. It should form soft peaks, not hard.
You can either serve the strata straight out of the baking container, or allow it to rest a bit, and cut portions. I prefer the latter for presentation. Serve with berries, whipped cream, and maple syrup.