Fill an OXO No-Spill Ice Cube Tray with water and freeze ice for cocktails. Repeat until you have a large bowl of ice ready for cocktails. Store in freezer. Transfer to OXO Ice Bucket when you're ready to serve.
Core 4 apples and cut into small chunks. Place enough apple chunks into the fruit tray of an OXO Ice Bucket Set to fill it. Place ice bucket in the fridge to keep them fresh for garnishing your drinks.
Cut 1 orange and 2 limes into slices. Cut the orange slices in half. Place the fruit slices and remaining apple chunks into a 2.5-quart pitcher.
To the pitcher, add the wine and apple cider. Use an OXO Steel Angled Jigger to measure the brandy and pour it into the pitcher. Juice the remaining 2 oranges and limes with an OXO Steel Citrus Juicer to keep track of the fresh juice amounts. You'll want 2-ounces fresh orange juice and 1-ounce fresh lime juice.
Stir together the sangria with an OXO Spinning Bar Spoon until fully incorporated. Chill the sangria for at least 1 hour.
Spread some cinnamon sugar out on a small plate. Run an orange half slice with a slit cut in it around the rim of a wine glass to moisten it. Turn the glass upside down and dip the rim in the cinnamon sugar.
Fill the glass 1/2 full with ice from your OXO Ice Bucket Set. Pour in the sangria until the glass is almost full. Garnish with 1 orange half wheel, some apple pieces, and a cinnamon stick. Serve immediately.
You can add more or less simple syrup to your liking. I didn't make this sangria overly sweet because of the cinnamon sugar rim on the glass.
To make rimming sugar for glasses: Combine 2 tablespoons sugar with 1 teaspoon ground cinnamon in a bowl. Spread out on a small plate.
To make simple syrup: simmer 1 part water to 1 part sugar until dissolved. Cool to room temp.