Caribbean Cocktails at Home : The Painkiller

Caribbean Cocktails at Home : The Painkiller

You arrive on St. John.  You disembark the ferry and head where?  Most likely your answer is happy hour!  Why?  Because you have been dreaming of your favorite island concoction since you last left and you can’t wait to get another one in your hand while you watch the sunset.  But, let’s face it, we can’t always run to the closest beach bar whenever we get a hankering for a favorite island treat.  So, I thought we might start helping you build your at home Caribbean cocktail recipe collection…Starting with the infamous Soggy Dollar Painkiller!

Many of you may not know this about me, but I was a bar tender on St. John for many years.  I worked at Asolare, Motu>Drink, The Terrace, Spyglass, The Bowery, Zozo’s at the Sugarmill and moonlighted on occasion at Castaways>Dog House Pub, Sushi St. John and 420 to Center.  Island cocktails were my first knowledge tree to climb when I moved to St. John in 2012.  I remember my first training shift at Asolare…I was pouring a drink and my cocktail goddess of a mentor, Kim Holland, told me to just keep pouring the rum when I paused at the “stateside normal” 1 1/4 ounce pour.  When the glass was half full of rum, she gave me the nod.  Ok, so that’s how we do things here…. 🙂

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I was thinking about things that my guests would always ask me while working behind the bar.  A lot of times, my content on the site comes from those stories that I used to tell over and over again.  Being a newcomer to the island, I would get hit with MANY questions I did not know the answer to.  So, I would go home and google, I would ask questions of the long time residents I was privliged to be working with….always looking for the answers.  Thus began my love affair with seeking out the history and “news” of St. John.

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But the one question I DID know the answer to rather quickly was “How do I make this drink at home?”   It was  my first area of expertise on St. John.  And, I feel like this info will be rather useful for all of you at home with a Caribbean thirst to be quenched!  So, I’m going start a little cocktail series here and see how it goes.  I’m going to start with the obvious, but will move through the list of what I consider to be some of the best cocktail concoctions on St. John (and, for this one, the BVI).  PLEASE, let me know your favorites in the comments and I will try to pry the trade secrets from the hands of the bar staffers of St. John over the next few months!

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I’m sure MANY of you have already perfected your “at home” Soggy Dollar Painkiller recipe for those chilly winter nights when you’re longing to be in the Virgin Islands and you need a “taste” of that familiarity.  But we are going to start there today for all of the newcomers in the group that maybe need a little coaching 🙂

First, a little history lesson on the Painkiller.  Did you know that this infamous rum cocktail is actually TRADEMARKED by Pusser’s Rum?  I did not and neither did a NYC bar of the same name that received a lawsuit from the small rum distiller in 2011 which forced the new tiki style cocktail lounge to close its doors!  Google that.  It’s crazy!

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Legend has it that the first version of a Painkiller was served at, you guessed it, the SOGGY DOLLAR BAR in the 1970’s.  The following excerpt is from the Pusser’s Website:

A version of the classic Pusser’s Painkiller® had its start at the six-seat Soggy Dollar Bar on a long stretch of white sand beach at White Bay on the island of Jost Van Dyke in the British Virgin Islands. There’s no dock, so the usual way in is to swim. Of course, your dollars get wet, hence the name “Soggy Dollar Bar.”

It was owned by an English lady, Daphne Henderson. Boaters, including Pusser’s founder, Charles Tobias, came from distant places to sample her version of the Painkiller for which she’d become locally famous. The fact that Tobias had gone to The Admiralty Board of the Royal Navy and gained permission to commercialize the rum in 1979 made him curious about this deliciously concocted recipe made with Pusser’s Rum.

Daphne Henderson and Charles Tobias became good friends, but in spite of their close friendship, and no matter how he tried, she refused to divulge her secret recipe for the cocktail. Two years passed. One late Sunday afternoon, after a morning spent “killing the pain,” Tobias somehow managed to get one of her concoctions back through the surf and over the gunwale into his boat, and ultimately into his kitchen on Tortola where he lives. There we went to work trying to match her flavor as closely as possible with his own recipe, which he finally worked out to be “4-1-1-1” ratio—four parts pineapple, one part cream of coconut and one part orange juice adding Pusser’s Rum to suit.

The following Sunday, Tobias returned to her bar and announced to the patrons on hand that he had finally broken her secret. So he mixed one of his and circulated it for comments. Tobias discerned a slight difference, but thought his mixture to be better, not quite so sweet as hers, and told her so. The ten patrons gathered around the bar unanimously preferred his version to hers, and the rest is history!

And, thus, a legendary cocktail that spans the Caribbean was born.  I know from my recent travels to Grenada that the Painkiller is on every drink list at every beach bar on those islands so far from home.  It’s a literal crowd pleaser.

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So, how do you make it at home?  Well, first let’s round up the ingredients:

  • Dark Rum– The obvious choice is Pussers, but on St. John Cruzan Rum is most widely used.  You could also try out the Soggy Dollar or Lovango Rum if you can find them!  Not white rum, not spiced rum, not Gosling’s style extra dark rum, but good old aged dark rum.
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Lovangos signature light and dark rum blends.
  • Cream of Coconut–  This can be found in the mixer aisle of most large grocery and liquor stores.  The one most commonly used on island is “Coco Lopez” although any sweetened cream of coconut will work.  It’s a pain out of the can, but that’s how it is most widely sold.  Shake it up and pour it into a squeeze bottle for ease of use.  You will need to refrigerate it after opening but it will separate once refrigerated.  Take it out of the fridge, let it defrost a bit and give it a good shake before the “next round.”  In recent years, I have seen it at stateside grocers already IN a squeeze bottle.  If you’re lucky enough to find it go that route!

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  • Pineapple Juice – in a can, in a bottle…Whatever your preference is fine.
  • Orange Juice– Same as the pineapple but if you want to take your concoction to the next step, use fresh squeezed oranges!
  • Fresh Nutmeg–  Not the stuff already in the shaker!  Get yourself some whole nutmeg with a microplane to give it that extra fresh and spicy aroma that truly makes a great painkiller.  If the bar tender at Soggy can do it with 100 Painkillers in front of him or her, you can do it too!

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Ok, so now you have everything all lined up.  You will also need ice and a cocktail shaker.  Perhaps also a jigger if you need help with measuring portions.

Here’s the recipe:

2 ounces Dark Rum

1 ounce Orange Juice

4 ounces Pineapple Juice

1 ounce Cream of coconut

Combine all ingredients in a glass and fill to the top with ice.  Now, shake the CRAP out of it!  You want to break up that cream of coconut and give it some nice little bubbles on top.  Pour your concoction back into the glass and top it with a healthy amount of freshly grated nutmeg.  Bonus points for you if you are using a Soggy Dollar cup for your cocktail creation 🙂


Ok, now, sip, enjoy, repeat.

Let me know how these go down at home…Bloopers and photos are great.  And, please, tell me what drinks you would like to see featured in this series!

Up next, the Bushwhacker 🙂

55 thoughts on “Caribbean Cocktails at Home : The Painkiller”

  1. Great article! As a local bar owner I can suggest that if you don’t have Pussers that a mix of Goslings and Cruzan Dark works very well, or the Brugal (a great bang for the buck Dominican rum). Always use good quality juices, and careful with the coco Lopez (too much and it’s way too sweet). Also, they don’t taste right if your toes are not in the sand… don’t know why that is.

  2. After a visit to Virgin Gorda, we returned to Colorado longing to
    have just one more Dark and Stormy. We would love to have
    this recipe and other tropical drinks to enjoy while dreaming
    of our return to ALL the Virgin Islands.

    Appreciating you,

  3. Love the Painkillers, and this will be an awesome series, thanks for sharing How!
    How about including an authentic BBC? (Personally partial to High Tide’s, but any will do!) So delicious! 🙂

  4. Wow, I love how you capture the essence of the moment, the experience of learning the drink and the island. You paint a picture with words.

  5. Love this article. We do have some of those original Painkiller ceramic mugs from Pusser’s and have enjoyed our “remote” happy hours over the years. We’re at the age where we decided to remove alcohol from the drinks. (Don’t ask — health, sanity, cost, etc. At least as this age we’ve found we can relax without it!) Is there a recipe for a painkiller and other favorites without rum? (Ugh!??) I’ve been able to create a suitable “grog” with tamarind, ginger beer, lime, bitters, and grated nutmeg. Any other ideas?

  6. I use a gallon milk jug and a funnel and use the coco lopez can as the measuring intrument.
    1 can Coco lopez, 2 Coco Lopez cans of Dark Rum, 1 Coco Lopez can Orange Juice, 4 Coco Lopez cans Pineapple Juice.

    I shake well after adding the rum so the ‘lumps’ in the coco lopez get broken up before the jug is too full.

    Put the jug in a cooler with ice, red solo cups, and a baggie with your nutmeg and grater…Instant party at the pool!

  7. Yummy! Can’t wait to try it!
    Also love Soggy Dollar’s rum punch with, what is it, cilantro leaf?
    I think these might be the most popular posts of all time!

  8. Each visit we search for the best PK on STJ. While most of our research in out east, we manage to include some Cruz Bay bars, too. Undefeated Champion is Skinny’s (Stateside, its mine).

    I’m really looking forward to this series. Big Fun!

  9. I always tell people the recipe is easy to remember 4-1-1 (like information) 4 parts pineapple, 1 part OJ, 1 part cream of coconut, plus dark rum and FRESH grated nutmeg.

    I just need to perfect a bushwacker now!!

  10. Had three Painkillers at my favorite non-STJ bat; Island Fever in Door County WI.
    Making your recipe tomorrow. Salivating already.

  11. Hi there,

    That’s the recipe I use at home back here in PA!

    I also mix up a patch if we’re taking a limo to the airport for travel to St John.

    No current pics, but the best was a suggestion to use an empty Vlad Vodka bottle for in the limo so I didn’t have to either pack or throw away a nice container.

    Will post pic next time I make them, we have a LOT of Soggy Dollar cups from our visits there.



  12. The raspberry margarita from Skinny Legs. I was there in June and loved it. Disappointed my wife would only allow one, as I was driving. I also second the rum punch.

  13. Not sure what a BBC is?.
    I love the Gin cocktail at Morgan’s Mango that has St Germain in it.
    Or my husbands GnT with Lime and fresh mint _ so refreshing on a warm evening.

  14. Love those Painkillers- have made that recipe at home several times and it’s awesome! Would also love the recipe for a Skinny Legs Coconut Swizzle. Yummmm!

  15. We had our first Painkiller at Miss Lucy’s. Was a revelation. I can always make my wife’s day when she sees me getting out the whole nutmeg and the microplane; she know’s what’s around the bend.

    We had Dark ‘n Stormy’s at a few places, but then we had one at the Aqua Bistro where I watched the bartender shake a few drops of bitters on top. I said, “I haven’t seen anyone else put bitters in before”. He side-eyed me and said, “You HAVE to have bitters”. It makes all the difference.

  16. “Just keep pouring the rum,” lol. I remember a lo-o-ong time ago, just after I became old enough to drink, ordering a gin and tonic on St. John. It was served, I sipped it – and almost gagged. My father asked to taste it and broke out in laughter. “It’s 5 parts gin and one part tonic,” he exclaimed. Gin was much cheaper than tonic, so go figure.

  17. What a great addition to the already wonderful information we get about the island. Please, please add Bushwacker to the list of recipes. My absolute favorite chocolate drink!

  18. I just wanted to say thanks for this great article and all of your articles It is truly enjoyed by all !! giving us this history and recipes makes life all the more happier Home away from home.
    love St. john be safe

  19. Rum punch, for sure! Not to be too demanding, but… the Caneel Bay rum punch recipe would be best — the one they served on the “Lady Caneel” on the ride over from Red Hook. It was the perfect way to start (and end) a vacation on St. John.

  20. This series is great! How can we make a “skinny” version of thrse drinks? Less cream of coconut….Love lime in D coconut.

  21. Thanks for the recipe Hillary. I’m sure we crossed paths when my wife and I used to run Estate Lindholm occasionally for Brion.

  22. I like your comments about your past employment and how it qualifies you to provide rum drink instructions. Let’s send out the recipe for the infamous Plantation Punch and the Rum Jumbie from Cannel Bay. Those are two classic rum drinks. If you do not have them, I can dig them up for you.

  23. Thanks for the article! How about a Bushwacker? Fantasizing about St. John while having hurricane cocktails during Hurricane Henri, in Mystic, CT…..

  24. Great idea,aftery lady cruise to Tortola and finally taking a long awaited excursion to Jost Van Dyke for an original Soggy Dollar Pain Killer,we were graced with an extended stay on the beach whilst waiting for another boat to take us back as ours broke down after running around when the engine had heated up.It was an unexpected pleasure for sure and enjoyed many extra Pain killers as a result lol.

  25. My wife and I have been coming to St. John for decades. Kinda scary to think how many. A couple of cocktails still stand out in our minds. The Kiwi Colada at J.J.’s and the Key Lime Pie at two different places in Mongoose Junction.
    Great idea for a series, and we will try and make ‘em all.

  26. We use the Coquito Trigo Coconut Cream, instead of the Coco Lopez. The color, consistency, and taste is fantastic. I’m not sure which bar told me about this mixer, but it’s definitely worth the effort to include in your next Pain Killer!

  27. George’s of Galilee here in Rhode Island does an excellent Pain Killer. You can get sand in your toes just like at the Soggy Dollar!

    Sorry – your site won’t allow a pic…

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