Hipster Pirate Recipe

This is how I make the drink known as the Hipster Pirate. Tybee Island, GA was frequented by pirates once upon a time (not this kind); an expensive and overly ethics-concerned coffee drink like a vegan mocha was considered just a bit of hipster ridiculousness by a lot of locals when I moved there. Therefore the signature drink at my Tybee cafe was named the Hipster Pirate. Also because hipsters like good coffee drinks and pirates like rum. :)


  • Splash of rum
  • Shot of espresso (or the result of your favorite alternate strong-coffee-brewing method — Aeropess, etc.)
  • Chocolate (syrup, powder, bar, your choice)
  • 6 – 13 oz. of your favorite non-dairy milk, depending on the size of your mug (regular milk works, too, but blech)

More on choosing ingredients in the instructions section.


I tend to have an ingrained belief that all alcoholic coffee drinks belong in clear glass mugs on stem bases, because I grew up for a while in a restaurant that served irish coffees, but any cup* or mug will work.

Hipster Pirate in a glass mug

I only made this with layers to show Westi.  — Photo by Peter Westwood

One thing that is cool about coffee drinks in glass mugs is that if you pour it all just right, you can see the different components of the drink as layers/stripes. Then again, you want it all mixed together before you drink it, so who cares about the pretty stripes? I much prefer swirling throughout assembly so it’s all one consistent liquid.

You can be fancy and make a ritual out of assembling this drink, or you can just bung it all together in the cup in whatever order you want. It honestly won’t make much of a difference unless you are using a harder chocolate source (broken up chocolate bar, chocolate chips, thick syrup, etc), in which case go with this fancy assembly order or something similar to give the chocolate the maximum melting time.

Put the chocolate into the mug of your choice. I have tried a few different forms and have a favorite, so here’s how I think they stack up in terms of this drink.

  • Chopped up bar chocolate. This certainly looks cool. If you chop it pretty fine, it will melt relatively quickly if you stir quickly once the espresso is added, but you’ll probably have some little unmelted nibs at the end. I like this method more in theory and aesthetically than in practice. If using this method, I like to go with a high-quality dark chocolate that has a low sugar content, but whatever floats your boat will work just fine, as long as it is actual chocolate — if what you have is really a chocolate-flavored bark of hydrogenated oils, it will be super gross.
  • A chunk of a chocolate bar. I reserve this method for when I am desperately craving that sweet mocha goodness but I’ve gone to Coava and they will do a latte but not a mocha. Then I buy one of their small bars of some artisan-or-other chocolate and drop it into a latte and attempt the same stir-to-melt action that I use with chopped chocolate. It’s better than nothing, but it does not melt anywhere near enough to be satisfying, unless you like the idea of a wet chocolate bar bite at the end, analogous to eating the fruit after you’ve drained a glass of sangria.
  • Powdered drinking chocolate (like the ones from Theo Chocolates). Works okay, but you need to make sure you get the powder absorbed in the stirring with espresso or you’ll wind up with little powdered dots floating to the top after you add your milk-style liquid, making your fancy drink look like it came from a packet of swiss miss.
  • Chocolate syrup from the store. Works well, but try to be sure to get one that is made with straight up cocoa and sugar, no oils, or you might get an oily sheen/droplets on the surface of your drink, also unappealing.
  • Homemade chocolate syrup. 1:1 ratio of sugar and water to make a simple syrup over moderate heat, add cocoa powder while heating to suit your level of intensity. Keeps well for a really long time in the fridge. Gold standard in terms of meltability, cost, no unappealing visuals on top of drink or in cup afterward. Make a batch in advance sometime and bottle it up for use whenever.

Grind the coffee beans. Two elements inherent in this instruction: the bean and the grind.

  • Given the option, I prefer to get something that comes from a direct trade source that is environmentally friendly, but that’s your call. Things I look at if I’m in a situation to be choosy about beans include agricultural methods, labor practices, bird policies, and impact of the farm or plantation on the local environment and/or ecoonomy.
  • I will also choose something locally-roasted if it’s available for a few reasons. The fancy coffee roasters have told me that you should use beans within a week of being roasted, 2 weeks at most (unless they’re in an unopened vacuum-sealed package), or it’s not worth it. Other people keep an open bag of beans for months and say they can’t tell the difference. Your call, but if you care about that stuff, local roasting definitely has an edge when it comes to getting coffee in the magic window of not-too-soon-after-roasting-and-not-so-old-the-taste-declines. Plus it supports a local business, often an independent proprietor, which tends to keep more money in your community.
  • I also (I know, I know, gasp and horror) prefer to get decaf if it’s water-processed. Caffeine is just really, really bad for you (side note: if you like literature, read Memoir from Antproof Case by Mark Helprin, it’s pretty great.) and even decaf still has way more caffeine than our bodies really want or need. Fancy coffee people will tell you that decaf is an abomination and utterly intolerable. I tell you that high blood pressure, anxiety, reduced motor control, withdrawal migraines, bone loss, insomnia, and other related health effects that could be prevented by ditching caffeine are the true intolerable abominations. And if you look into the water process, it’s almost like you get coffee soaked coffee — the decaf I’m talking about is not weak, it’s delicious.
  • Fancy coffee people will say that you should grind immediately before brewing or it’s not even worth it. Since I was running a cafe that did fancy coffee, I followed this advice so the coffee would get its best shot (heh) at making a good impression on the customer. However, if you don’t have a grinder and you buy pre-ground beans, who cares? I mean, it’s the flavor you’re used to, so it won’t taste like crap to you, right? That said, if you do have a grinder, grind the beans at the appropriate grain when you’re ready to brew, and only grind as much as you’ll need.

Brew a shot of espresso (or conduct your alternate strong-brewing technique as mentioned above to acquire an equivalent amount of liquid, about an ounce, but the bullet points below refer to brewing traditional espresso) directly into the cup holding your chocolate. That said, if you don’t have room to do this because you chose a giant cup that won’t fit under your portafilter, it’ll be fine, don’t sweat it.

  • The scalding espresso will start dissolving the chocolate immediately, turning into a coffee-cocoa liquid love child.
  • You won’t lose the crema the way you do when you brew into a demitasse/shot glass/small pitcher and then pour from that into the bigger mug.
  • Depending on what kid of chocolate you used, either give the mug a swirl to ensure a good mix, or stir it with a spoon if needed.

While the shot is brewing, steam your milk-type liquid. Don’t go too hot. I used to use soy as a default, but have since switched away to hemp or almond or coconut or hazelnut or some such, now going to soy only when it’s the only option. Try not to get crazy with the foam — microfoam is your friend. Fancy coffee people will want you to give your steaming pitcher a couple of taps on the counter and a swirl to settle before pouring the liquid into your mug. This is okay, because it gives you a second to pour a splash of rum into the coffee-cocoa love child mixture.

Pour a splash of rum into the coffee-cocoa love child mixture. Fancy liquor distributors might tell you all kinds of things about various producers and varieties, but forget ’em. Just get some basic plain white rum at the liquor store.

Pour in your steamed milk. The pouring will swirl together the ingredients already in the mug, so you shouldn’t need to stir it unless you are still trying to get solid chocolate to melt or something. Or unless you made layers because you think they are pretty, in which case admire the pretty and then stir it out of existence. Fancy coffee people make pictures likes leaves and hearts and other elaborate markings in the microfoam. I don’t bother, but if you want to learn it is not hard and there are lots of latte art instructional videos online.

Put your hands around the warm mug and feel cozy.

Drink your hipster pirate and feel warm and snuggly and like one big contented sigh. That is all.

*It’s worth noting that the hipster pirate can also be enoyed in a to-go cup, but I do recommend reusable travel mugs over disposables — those “compostable”  paper cups are mostly lined with corn-based plastic and will almost certainly not be composted unless you live somewhere with a commercial composting facility willing to accept them. I live in a composting mecca and even we can’t compost these damn cups.