'Tis the Season for Boozy Sweet Drinks

Yes, there's a lot of chocolate involved.

The line between sweet and saccharine is a fine one, especially when it comes to cocktails. As the weather gets colder, we're especially prone to adding a splash of orgeat, amaro, or Cognac to many of our favorite drinks, and find that as long as (some) caution is exercised, the result is absolutely delicious. Join us by making a few mugs of boozy hot chocolate, a toddy that's anything but ho-hum and traditional, or a creamy, unexpected absinthe milkshake. Here are 13 of our favorite sweet cocktails to make when we're craving a little something extra to end the night in style.

Little Lebowski

Expect Eggnog, amaro, coffee liqueur, and lots more cold weather deliciousness ahead.

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Rockin' Around

While a drink flavored with strawberry liqueur (which we swap for easier-to-find raspberry liqueur) and lime might not feel like an immediate choice for the holiday season, we guarantee one sip of the Rockin’ Around cocktail will change your mind.

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Mudslide

Created in the 1970s at Grand Cayman's Wreck Bar at Rum Point, this potent blend of vodka, Kahlúa, and Baileys Original Irish Cream might taste like a milkshake, but it can't be ordered virgin because all you'd get is a cup of crushed ice! The trio of alcohol blends into a smooth and velvety cocktail just sweet and chocolaty enough without being cloying. A generous drizzle of chocolate syrup and a bright red maraschino cherry with a dusting of ground cinnamon top off each glass.

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Naughty List

The Naughty List is a boozy hot chocolate that we can’t wait to make as soon as the temperatures drop. At the Dead Rabbit, you'll find this cocktail garnished with grated nutmeg — we opted for sprinkles for an extra pop of color.

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Tom and Jerry

Boozy, creamy, and comforting, you'll never regret making a batch of Tom and Jerry cocktails.

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Overstory Toddy

This soul-soothing tea-based cocktail is light on the booze and packed with smoky sweetness. Benedictine and vanilla syrup make for a truly silky mouthfeel, while the acidity and brightness of verjus cuts through the sweetness. A backbone of Irish whiskey keeps things serious.

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Affogato Martini

Gelato tips this Espresso Martini further into dessert territory.

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Sgroppino

Who says Sgroppino is just for the summer months? This snowy white sweet treat is ideal for entertaining.

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Tropical Rum Punch

Cream of coconut and pineapple juice make this punch feel like vacation in a pitcher — even if it's freezing outside.

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Guava Goddess

If you love Aperol, Tequila, and making drinks for a crowd, this batch-friendly cocktail is for you.

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Raspberry Frappé

This frozen cocktail is especially perfect for fans of sherry and comes together in minutes with the use of a high-powered blender.

Absinthe Milkshake

A vanilla milkshake gets an adult upgrade with a decent amount of cherry liqueur to brighten things up and a generous dollop of absinthe.

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Upset the Applecart

Ginger syrup, applejack, and chai come together in perfect harmony to make this sweet, spicy, and smoky autumnal cocktail.

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Retropolitan

Infusing Aperol with strawberries overnight creates a dessert-like cocktail for sweet sipping.

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