Pain Killers at the Soggy Dollar Bar, Feeling Fine at Foxy’s and Getting Naked at Willie T’s All Part of the Ultimate BVIs Sailing Experience

The appeal is obvious – rum drinks on tropical beaches. Warm weather, the water right there to jump in and cool off, and beaches in which to sink the toes in the sand. I envisioned jumping off the starboard rail of a sailboat into aqua-colored water so clear I could see the bottom, swimming and snorkeling, then wandering up to a bar in a wet bathing suit and having a series of boat drinks.
To accomplish this feat, I thought I needed two things: A lot of money or a lot of luck. The reason is that about the only way to do it is by charting a boat, and that involves having someone that knows how to skipper it and how to navigate the waters, which includes actually finding the bars. I knew this because I had spent a week on St. John’s with a friend, who’s wife’s parents own a house there. He took us out on his boat one day and while we didn’t whoop it up, I did get enough of a taste of the place to want to do it all exclusively on a boat.


Well, as luck would have it, I eventually achieved this bucket list item. I went along on a “party cat” as part of the annual Interline Regatta, a 10-day drinkfest, er, regatta, for employees of the airline industry. Yes, I had friends in the industry, but anyone adventurous enough can tag along, as long as they charter their own catamaran. The event calls for having theme parties every night at just about all the islands and bars in which I had envisioned visiting, including a couple of which at the time I was not familiar.
And let me say, it was not only way cool, it exceeded everything I had ever envisioned! Granted, having 800 people (including stewardesses) along partying like crazy every night helped – the Virgin Islands are not exactly Mykonos on a regular basis – but the bars are cool and the rum is plentiful.
In fact, I soon quickly discovered that the rum is cheaper than the mix, so drinks are something like 60% rum. At every location, I ordered a rum punch and this was like having gumbo in New Orleans: Each one was a tad bit different but each was great.

My favorite spot was not the Soggy Dollar Bar, some may be surprised to learn, but Willie T’s. This is an old pirate ship permanently anchored at Norman Island and the place can get absolutely NUTS! The bartenders pour especially liberal here – especially to girls – and people get naked and jump off the back into the water. I had a bit of trouble climbing back onto the dock, eventually having to straddle a dingy, much to the amusement of the people dining in the front of the boat. Why don’t they put up swim steps!?
The Soggy Dollar is great, by the way. We anchored in the harbor, jumped overboard and swam to shore. I had thought that the place was in the middle of a lagoon or something; it’s called the Soggy Dollar because people swim to the bar and their dollars arrive soggy. There’s a clothesline above the bar where the greenbacks are set out to dry (and yes, they use greenbacks even in the British Virgin Islands).
In reality, you can take a dingy to shore but what’s the fun in that, right!? (Actually it’s nice have one there after several drinks!) The Soggy Dollar Bar is really just a small shack on a beautiful white beach. Palm trees block the view from the harbor so if you don’t know it’s there you would sail right past it. Of course, any skipper worth his or her salt knows the location of the Soggy Dollar!
And while I drank several Pain Killers – and have a few dozen of the small plastic souvenir cups around the apartment to prove it – I actually prefer the Bushwackers made up by a slow-moving Caribbean lady, Gertrude, at her place Gertrude’s.
I had a very special moment as we sailed into Cane Garden Bay. For years, I had listened to the lyrics of that Jimmy Buffett song about the place, and as we rounded the corner and the harbor came into view, I put Manana on the stereo. (We then hit something on the bottom of the harbor!) The bar there is called Myott’s and the whole night I felt as if I were living a song. Which, of course, I was, and that was great.
The regatta schedule did not visit the most legendary bar in the entire BVIs, Foxy’s. That’s because the regatta is in mid-October and Foxy doesn’t open until sometime at the end of that month. Or perhaps November. However, I did get there on a second trip. A friend, Eric Stone, is a musician who plays his original island music at all the bars and he was scheduled to play Foxy’s on New Year’s Eve.
He offered an invitation to join him, so not only did I get to Foxy’s, I was there for its legendary New Year’s Eve party! Talk about being lucky.
So if you love the beach, beach bars, rum drinks and can sail or you know someone who can sail, the Virgin Islands are a perfect place to spend a week. For a detailed look at all the bars of the BVIs, click here.
Cheers!
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