The 10 Best Cocktails To Pair With A Box Of Chocolates, According To Experts

When it comes to gifts, some of the most popular are flowers, a nice bottle of wine, and, of course, a box of chocolates. It doesn't matter if you a buy a premade box or pick out all the pieces yourself, that box will almost certainly contain a decadent mixture of dark and milk chocolate, nuts or caramels, and probably a few luscious creams that melt in your mouth. While we all love to pair a rich piece of dark chocolate with a full-bodied red wine or sweeter port, not everyone loves wine. Some actually prefer a cocktail instead. Something you can sip and savor while casually making your way through that enticing heart-shaped box. 

But with the thousands of cocktails out there, we wondered which would go perfectly with that chocolate-covered cherry or caramel turtle? Should you go with a clean, crisp martini, or would something sweet and creamy be the better choice? Should it be served up or on the rocks? And while we strongly believe that most drinks are better with a splash of bubbly, will those same bubbles pair with your favorite bonbon? Well, wonder no more. We spoke to a few people in the cocktail industry and heard directly from those who know which drinks make the perfect partner to that alluring box of chocolates.

These days, if you want a cocktail with a distinct coffee flavor, odds are you're going with either an espresso martini or an Irish coffee. But just because the White Russian isn't the drink of the moment doesn't mean it doesn't deserve a sip. This drink has been around since the '60s, and while it might have been enjoyed occasionally here and there, this simple elixir was often considered an uncool cocktail. That is until Jeff Bridges' uber-cool character, the Dude, was seen drinking it all the way through the 1998 film "The Big Lebowski." 

A simple mixture of vodka, Kahlúa, and cream, this drink is the perfect accompaniment to a piece of dark chocolate. Its delightful coffee flavor comes not from coffee but rather from the popular coffee liqueur Kahlúa. And since we all know how well coffee and chocolate go together, these two seem like a natural pair. But it's not just the coffee that makes this the ideal choice for that decadent truffle; the thick, rich cream that's blended into it is the ideal match to any of those bites that come with a creamy center. 

There's no cocktail more popular these days than the espresso martini. It's so popular that bartenders are starting to put their own spins on it, from changing out the base spirit to adding a variety of flavors like caramel apple. So, it came as no surprise when three different cocktail experts recommended it as their number one drink to pair with chocolate. "The cocktail that first sprang to mind for this pairing was a classic espresso martini," explains mixologist and frequent "Bar Rescue" consultant Mia Mastroianni. "Vodka, coffee liqueur, and espresso. Boom. Coffee and chocolate are such a natural pairing, and an espresso martini would complement any filling, nougat, truffle, or nut cluster." While drink expert Daniel Ufland concurs, he believes this cocktail goes best with dark chocolate. "The creamy texture of this cocktail balances the dryness of high-cocoa dark chocolates, making it perfect for dark chocolate lovers," he explains. 

But if you're not a vodka fan or want to add an extra level of flavor to your drink, Mastroianni tells us you could substitute the vodka with coconut rum or peanut butter whiskey. "Both lend themselves to the flavor profile and would still complement a chocolate pairing." Out of those two choices, entertaining expert Paul Zahn says he'd opt for the peanut butter and use Skrewball Whiskey to make it. "The nutty notes from the coffee and peanut butter whiskey make this the perfect drink to pair with chocolate," he says. But it wouldn't be a simple substitution. Zahn likes to cut back the Kahlúa and add a little more whiskey "just to allow for the nutty notes to really pop." 

Keeping with the creamy cocktail theme, we have the Brandy Alexander. Another decadent Prohibition drink that makes for a wonderful nightcap or drinkable dessert, especially since some liken it to a boozy milkshake. When it first appeared on the scene at the turn of the century, it was simply called an Alexander and made with gin, cream, and crème de cacao. But in the '30s, the gin was swapped out for brandy and dusted with a little fresh nutmeg. You still have the same delicious tipple, just a different spirit, which, of course, means a different flavor. A flavor that has a little more depth and intensity.

But since we're talking about pairing chocolate with cocktails, let's get back to the other liquor used in this drink — crème de cacao. While you could go with light or dark for your cocktail, the darker version tends to have a more intense chocolatey flavor. More chocolate means a better match to that heavenly box. In fact, bartender Brynn Smith believes the combination of "cocoa and cream with chocolates give a richer, decadent vibe," thereby making the whole dessert experience even more luxurious.

Another popular cocktail that's ripe for twisting is the old fashioned. A seemingly simple drink comprised of whiskey, sugar, and bitters, this drink has stood the test of time and become a perfect choice to imbibe before, during, or after dinner. Because of its simplicity, this is another drink mixologists have been tampering with for ages. They may start out by practicing and perfecting the classic recipe, but eventually, they start experimenting by switching out the spirit or adding flavors like chocolate and caramel to make something even more interesting and enjoyable. We've seen tequila old fashioneds and occasionally gin. But if you're enjoying a box full of chocolates laced with caramel, Daniel Ufland recommends sipping on one with a little salt. 

The drink expert prefers a salted caramel old fashioned because the hint of salt combined with the caramel and vanilla notes often found in certain bourbon whiskeys enhances the buttery flavors of rich caramel. "The way the bourbon's warmth and caramel depth complement the creamy, salted richness of caramel chocolates is unmatched," he explains. "It's the ultimate pairing for those who love a balance of sweet and bold." 

If you prefer tequila over whiskey or vodka, you're not alone. Paul Zahn prefers sipping tequila with chocolate as well. But not just any tequila will do. "I love pairing chocolates with cocktails made with reposado tequila," he declares. His cocktail of choice? A Manhattan made with tequila. 

"A tequila Manhattan is the perfect drink to sip while trying some chocolates," the cocktail expert explains. He prefers Codigo because it doesn't have any additives and is aged six months in French oak wine casks. Aging the tequila in those casks gives the spirit some nice vanilla and caramel notes. Notes that Zahn believes pair especially well with a plain piece of chocolate. If you're like us, however, and prefer your chocolate to have a little extra flavor, don't fret; the Manhattan still works because it includes sweet vermouth in its mixture that Zahn believes "will also make those cherry chocolates in the box really pop." 

But if you don't want to put in the extra effort of mixing up a cocktail, Zahn recommends enjoying the reposado tequila neat because he believes pairing the agave spirit with your favorite chocolate makes "for a lovely experience."

Like so many pre-Prohibition cocktails that have stood the test of time, the Manhattan has had its fair share of twists and mash-ups. Some are instant hits, while others die on the vine. But one twist that has lasted and Brynn Smith says goes great with chocolate is the left hand cocktail. If you're unfamiliar with this drink, it's a newer classic that was created when New York bartender Sam Ross came up with the idea to marry a Manhattan and negroni together while swapping out the Angostura for some chocolate bitters instead. 

The final result is a drink whose flavors are a wonderful mixture of spiced fruit and chocolate, two things you'll probably find in that chocolate box. Smith explains that the bourbon, coupled with the bitter Campari and the "rich spiced and fruit notes of the sweet vermouth and cacao bitters, ties it all together while eating delicious chocolates." Sounds like a winner to us. 

For those who like their cocktails to have a bitter bite, no drink is better than the classic negroni. Comprised of just three ingredients, gin, Campari, and sweet vermouth, it's the Campari that adds a bitterness that just begs for a sweeter element to complement it. We can't think of a better companion than a rich piece of chocolate, especially if it's a sweeter milk chocolate. But we're not the only ones with this belief. Daniel Ufland agrees, telling us that the "negroni is always a well-loved cocktail choice." 

But while we'd be fine sipping on the unaltered Italian classic, Ufland suggests one minor adjustment: adding a raspberry liqueur. "Although a classic negroni ... can be slightly bitter for chocolate, adding raspberry liqueur softens the edges and plays beautifully with silky milk chocolate," he explains. The citrus notes from the aperitif coupled with the berry notes from the liqueur add a fruitiness that makes this cocktail truly satisfying.

As much as we love the negroni, sometimes it's a little too much for us. Sometimes, we want something that still has a touch of bitterness but isn't overpowering. In those instances, we reach for an Aperol spritz. Another cocktail based out of Italy, we opt for this aperitif when we want something a little lighter, something with a lower alcohol by volume (ABV), and something with bubbles. Unlike Campari, Aperol has more of an orange flavor and is sweeter than its Italian cousin, making it the optimal choice for those wanting to dip their toe into the bitter world of aperitifs. 

But we picked it as a proper suitor to that delectable confectionary box because if you're a fan of chocolate-covered cherries, strawberries, or oranges, the citrus notes of this cocktail only enhance those various fruit flavors. Its subtle herbaceousness and underlying notes of vanilla also pair well with those dark and nut-filled chocolates. When coupled with the effervescence of the prosecco and soda, you end up with a combination that's perfect for any celebratory occasion.

One of our favorite sweet treats is fruit covered in chocolate. It doesn't matter if it's a plate of freshly dipped strawberries or a box of dark chocolate-covered cherries. But one of our favorite fruit and chocolate combinations has got to be chocolates and raspberries. The rich earthiness of dark chocolate combined with the tart pop of fresh raspberries just sends us over the moon. Mia Mastroianni heartily agrees, insisting that "There's no greater combination of flavors than chocolate and raspberry."

So, it comes as no surprise that with a declaration like that, the "Bar Rescue" collaborator suggests a bramble as the cocktail to imbibe with your favorite chocolate. One of the few drinks to come out of the '80s with plenty of esteem, the bramble is simple to create since it only has four ingredients: gin, lemon juice, crème de mure, and simple syrup. Served over crushed ice, Mastroianni says, "It offers up a certain crispness, while not being overly sweet. A perfect pairing for a box of chocolates!" 

When it comes to celebratory cocktails, there are so many to choose from, it can be hard to decide which is best suited for which occasion. You have the classic Champagne cocktail, a French 75, and, of course, the Kir Royale. They're all stunning to look at, thanks to the coupes or flutes the drinks are usually served in, and they're all equally delicious. While each drink includes sparkling wine as one of its main ingredients, the other spirits change depending on which one you're sipping. But when pairing Champagne or sparkling wine with chocolate, there's really only one clear cocktail choice — the Kir Imperial. 

You may be well acquainted with the imperial's cousin, the Kir Royale, which is a simple mixture of sparkling wine and crème de casis, a black currant liqueur. The Kir Imperial is similar in that it also uses sparkling wine as one of its two ingredients. But instead of crème de casis, the Imperial typically uses Chambord, a raspberry liqueur. As we mentioned earlier, if there's one flavor combination of which we can't get enough, it's raspberries and chocolate. So, why not go all in on that flavor profile and sip on a sparkling raspberry cocktail while enjoying those fruity chocolates? And since this drink has only two ingredients, you can mix it up in the same amount of time it will take you to open up that sumptuous box.