If there’s ever a time when it’s most accepted (and expected) to sheepishly scarf down, reluctantly give in the form of a gift, or elegantly enjoy the sensual company of chocolate, it’s probably sometime around the second week of February. Or, if you fall into such a category that embodies frequent indulging, one of which, fortunately, doesn’t require any sort of rehabilitation known as a “chocoholic,” then maybe the middle of the summer is as good a time as any. But either way, I feed off my hopeless-romanticism and affectionate appreciation of wine and chocolate’s sensuality to share with you what I have only recently learned; the differences in chocolate quality, the potential health benefits (while minute) in select chocolate that is devoid of high sugar and/or milk levels, and which chocolates are most compatible and enjoyable with wine. I’ll attempt a concise divulgence of a few extraordinary (even revelatory, to me) wines that will indubitably create a memorable experience and oblige your sweet tooth (perhaps without excessive sugar!).

Firstly, this rather autonomous endeavor into the chocolate world has, while unintentionally, transparently flourished my love of wine towards a more relatable perspective. Just as wine becomes wine through the process of fermenting the juice from grapes, chocolate becomes chocolate through the process of fermenting the cacao (loosely interchangeable with ‘cocoa’) beans. Consequently, wine grapes are to grapevines what cacao beans are to the cacao trees. However, wine’s level of novelty doesn’t quite match that of chocolate, and I argue this through the quote of Wine Spectator’s Features Editor/chocolate enthusiast, Owen Dugan: “Almost everyone loves chocolate, and has from a young age. As a result, opinions are confidently and readily expressed—much more so than with wine for most people.” And in reflecting that, I can conclude that this blog would be rather purposeless if that weren’t the blunt truth.

So, once we’ve located a nice cacao tree, we’re making a little progress towards enjoying wine and chocolate with our significant other on Valentine’s Day. It’s not easy though, seeing as cacao trees only exist in areas and climate twenty degrees north or south of the equator. The Ivory Coast in West Africa is responsible for more chocolate production than anywhere in the world.

These are the colorful gourd-like pods full of beans that are cut from the trees.

This is what they look like when they are opened up, with the beans covered in white, sweet, gooey pulp and seeds.

Once covered with banana leaves, the beans, with the pulp still attached, begin to ferment for a few days, typically not longer than one week. At the point above, they are bone dry and are about half as dense.

Then the beans are roasted, deshelled, ground, liquefied and converted to either cocoa solids or cocoa butter, both of which make up the final product; chocolate.

Now, we’re ready to incorporate the booze into the equation. The questions are as follows: What works and what doesn’t? How/why is wine a sensible choice for chocolate? What should you drink with creamy milk chocolate or bars filled with ganache? (Hell, what is ganache?) What should you drink with bittersweet dark chocolate? Believe it or not, you’ve got quite a bit of options. And fortunately for those of you who still can’t quite stomach that nasty, sour (dry) stuff that lacks the sweetness you require in an alcoholic beverage, you may find yourself, at the very least, in luck, if not in heaven.

Rule number one: Let the drink be sweeter than the dessert. This is one to which I’ll deny you the satisfaction of details; try experimenting with it vice versa and see why. Also realize that sweetness does not have to be anywhere near synonymous with sugar. Most basically, a reasonably young wine with a substantial amount of ripe fruit and not too much astringency or obscene oak would be a nice fit with chocolate. (For the purposes of higher compatibility rates, let’s say we’re talking more exclusively about dark chocolate until otherwise noted.) Also, leaning towards red wine would be a safer bet in most scenarios. Wines like Cabernet or Merlot that you drink on a regular basis would be great as long as you keep the aforementioned factors in mind. As you hopefully realized in my last post, not every wine obtained from the same grape possesses the same characteristics, and obviously not all wine is young. Luckily, the market is much more stocked with younger wines than older vintages anyway, so it won’t be a difficult task to find them.

If, however, you’re looking for the wine that suits the special occasion, such as this upcoming one, you’re (hopefully) going to want to spring for the wine that’s quite literally made for special occasions. Port wine may very well be considered the ‘crème de la crème’ to be drunk with fine chocolate. Port, invariably hailing from Portugal, has a natural sweetness as its fortification process (the addition of the spirit of brandy) abruptly ceases fermentation, preventing the natural sugars in the juice from converting into alcohol as they normally would. And although said sugar is not converted into alcohol, the added brandy more than compensates to produce wines that are typically around 20% alcohol by volume. Port divides itself into a few different categories. Ruby Port would be the youngest, most simplistic version. Vintage Port would be the most complex, comprised of wine made exclusively from one single harvest. The middle-of-the-road style and arguably the best match with chocolate is called Tawny Port. In this style, you will often see bottles that are labeled in rather similar fashion to whiskey bottles (e.g., 10, 20, or 30 years old) as opposed to a single vintage. This is a barrel aging process called solera that assures what you’re drinking is unequivocally NO LESS than the given age on the bottle (say 10 years old), while some contents of the wine may have been added in from barrels containing even older wine (20, 30, or 40 years old). Chocolates that have hints of dried fruit flavors or actual dried fruit inside the bar are precisely the type of chocolate that wine, especially Port wine, craves. As you compare such organic similarities in making wine and chocolate, it becomes clear as to why the two have a primitive bond.

Another factor to keep in mind when pairing wine with chocolate is the cocoa to sugar ratio, which is indicated by a percentage of cacao. The lower the percentage, the sweeter the chocolate, the more likely some milk solids have found their way into the bar, and the less likely the beneficial antioxidants will be as present. As alluded to earlier, milk chocolate and wine are not always the most harmonious match (dark is the way to go, seriously!). But if you are indeed up for the challenge, another Portuguese fortified wine known as Madeira could quite believably satisfy. This wine often emanates a more nutty, caramel-like flavor than Port but still maintains the same sweetness that could hold up to a very creamy chocolate, even one with a mouth-watering, ganache-based truffle filling.

Some of the more aspiring chocolate enterprises these days that are devoted to unveiling chocolate’s most raw purities are based around the ideas of single-origin and bean-to-bar production. They’re both rather self-explanatory as single-origin represents a chocolate made from beans acquired from one single location, and bean-to-bar is a type of producer that certain ‘chocolatiers’ now pride themselves on by sourcing beans and never leaving their side from that moment until the end of manufacturing. Apart from achieving the most complex end result in a piece of chocolate, I find this most impressive for this reason: winemakers have it relatively easy in the sense that wine can be made from grapes growing on vines in any one of the 50 states, in so much of Europe, Asia, Australia, South America and so on. But in order to receive any certificate of authenticity with chocolate, especially of bean-to-bar-producing stature, you’re going to have a tricky time keeping up with the progress that starts and spends most of its time in tropical jungles.

Now that we’ve reached our culmination, hopefully you’ve got your ideas narrowed down a bit. If the Reese’s or Russel Stover’s heart-shaped chocolates are your gift for Valentine’s Day and you’re craving nothing but a glass of milk with them, I’ll understand. But there is some absolutely amazing chocolate out there, infused with herbs, salt, spices (quite literally chile peppers), coffee, even wine itself, and it doesn’t take much effort to fall in love with—certainly not as much effort as it does with wine, I admit it. That being said, it’s all about the second sip. Many red wines and Ports impart some faint but innate chocolate notes as it is, and once you remind the wine of that by biting into a piece of bittersweet dark chocolate laced with similar flavors, the second sip should help break down the alchemy that is wine and chocolate, collectively. Cheers.