I’m not a jealous guy….usually. But when I saw my friends post that they’re on their way to one of my favorite islands in the world, St. John in the USVI, I wanted to just drop everything and join them.
I’ve been to St. John at least 7 times, whether solo, or with family and friends, and I always had a dream of retiring there…that is, until Hurricane Irma devastated the island almost to the day 6 years ago. (September 6, 2017) It changed St. John forever, and I haven’t been back since before that catastrophic event. I am long overdue.
I thought about the many trips I’ve taken there, and the mandatory catamaran trip we took to sip Painkillers at my all-time favorite beach bar, the Soggy Dollar on the island of Jost Van Dyke in the British Virgin Islands.

The Painkiller is one of the tastiest rum drinks you can make, and one that certainly brings you back to the Caribbean. And it was invented at the Soggy Dollar. Located on White Bay, a stretch of the whitest most beautiful sand in the Caribbean, surrounded by sparkling turquoise waters, there is no dock. You have to anchor your boat offshore and swim…hence the name: the Soggy Dollar.
Daphne Henderson was the owner of the Soggy Dollar years ago, and she is credited for inventing the Painkiller, which used Pusser’s rum, a British rum that is readily available here in the United States. Charles Tobias, a businessman that received permission from the British Royal Navy to commercialize Pusser’s rum in 1980, tasted the Painkiller and realized the potential of this amazing drink. He took some Painkillers home to the island of Tortola, where he experimented in recreating that drink, coming up with what he thought was something that was as good as—if not better than—the original. He called it the Pusser’s Painkiller.
Tobias never found out what Daphne Henderson’s original recipe was, but when he brought his own Pusser’s Painkillers back to the Soggy Dollar, and had a tasting battle between the two recipes, legend has it that his recipe won 10 out of 10 times. With Pusser’s bars and restaurants in the Caribbean and more in the states, Tobias quickly made the Pusser’s Painkiller the signature drink of these now-famous establishments…and perhaps the most popular drink among the sailing community in the US, Caribbean and West Indies.
The drink itself is simple…
PUSSER’S PAINKILLER
4 parts pineapple juice
1 part cream of coconut
1 part orange juice
Combine these 3 ingredients, with lots of fresh grated nutmeg in a glass with ice. How much Pusser’s rum you use depends on how hammered you want to get! A Pusser’s #2 uses 2 parts rum…a Pusser’s #3 uses 3 parts rum…and a Pusser’s #4 uses 4 parts rum!
I’ve had several Pusser’s #4’s back when there was a Pusser’s bar on St. John many years ago. I’ve also sampled them in the BVI at the Pusser’s locations on Tortola. But I still prefer going back to Jost Van Dyke and knocking back a few at the place where the Painkiller was born, the greatest beach bar on planet Earth: the Soggy Dollar Bar.

A short time ago, there was an article that posted what they claimed was the original recipe of the Painkiller from the Soggy Dollar. It seems the only difference between the original and the Pusser’s version was the ratio of pineapple to orange juice. That’s just a personal preference.
Recently, the Soggy Dollar folks upped the game by putting their name on a line of rum. I just saw it in the store the other day, and have not yet had a chance to try it.

Whether you use this rum, Pusser’s, or whatever your favorite rum is, fact is, the best Painkiller is the one in your hand!
Hey Alz, To quote CCN , Its been a long , long time” Read your Soggy Dollar post with many emotions. I did not celebrate Labor Day weekend last week. Instead I had friends over and paid tribute to Jimmy Buffett by making the painkiller recipe in your post. It was good but the critical ingredient was missing, The Soggy Dollar Bar and beach. The memories helped but it still came up a bit short. I heard through that ancient, tried and true mode of communication, word of mouth, that you met up with my Marion electrician Mark Farrell at the Boathouse. I will be up north the end the Sept thru early Oct . Perhaps we can catch up at the Boathouse Bar. Russ
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Hey, Russ!
Good to hear from you! Hope you guys are doing well.
Yes, I did meet your friend at the boat house!
Would be great to see you, but I will be out of town for part of the end of September into early October.
So just let me know what your plans are, and maybe we can make it happen.
Take care!
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