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A Soggy Dollar Well Spent

Updated: Mar 31, 2022

When stories are told of adventures and antics in the British Virgin Islands, a great many of them start, end, or run through the Soggy Dollar bar on Jost Van Dyke. Just yards from the beach on the aptly named White Bay, the Soggy Dollar earned much of its reputation due to the potency and popularity of their signature drink – the Painkiller. A signature cup full of OJ, Pineapple Juice, Cream of Coconut, Pussers Rum, Overfidence, and Bad Decision Making garnished with a dash of fresh grated nutmeg. The miracle of the first one is how quickly it morphs into the third. And at that point, your day is off in a different direction from where it started.

Those of us who’ve taken a turn or two on White Bay know that the worst kept secret in the BVI is to pre-game with lunch next door at Hendo’s Hideout. My friend Ehren and his family have been working to thoughtfully develop their land on White Bay for at least the last decade. They’ve taken their time to get it right, and have managed to create a landmark destination just yards away from the most famous watering hole in the BVI.

After dropping anchor in White Bay, completing the obligatory swim to shore, and enjoying a fantastic lunch at Hendo’s our hearty crew cruised down the beach to the Soggy Dollar where Art’s phone pinged with a message from Carrie – our intrepid leader back at Timbers Kauai. She had sent a treasure map complete with cryptic, yet poetic instructions. Carrie is no stranger to these sands having lived in St. John for some blurry number of years.

As everyone worked to decipher the clues to solve the puzzle, sort out the map, and claim the prize, we soon found ourselves at the bar at the Soggy Dollar where we discovered that the “Treasure” was a round of Painkillers Carrie had “hung on the board” for our crew. What an awesome surprise!

We raised our refreshing glasses to the sky, toasted Carrie and her good nature, and agreed that no matter what happened in the next 2 hours, we would meet back at the boat ready to sail on to Little Harbor.

I’ll leave the details of a fun filled, rum filled afternoon to your imagination. As they say: “What happens on Jost stays on Jost.”

The sail across the island to Little Harbor was fueled by a stiff breeze and a festive reggae soundtrack as the crew kept the party going until we tied up at one of my favorite spots in the Caribbean, Sydney’s Peace and Love. Sydney is no longer with us, but his daughter, Strawberry has been a fixture here since childhood and carries on the tradition of hospitality that made this stop mandatory for every sailor in the know in the BVI.

After a lobster feast fit for Caribbean Royalty, we tucked in back on board Annilola and prepared for our last couple of days at sea.

Clearing back through customs and in to the USVI is most easily accomplished on St. John. My wonderful co-captain Mia spent the winter here a couple of years ago, and set up an island tour excursion for our folks with Liz Beal of USVI Expeditions. Liz is a phenomenal guide, and really showed off the best sights and views on the island before joining us for a boisterous dinner at Morgan’s Mango and the obligatory last night on board dance party and karaoke extravaganza.

Our last day of sailing was probably our most exciting. We danced between (& sometimes through) a maze of squalls that fueled a stiff breeze and lively seas. These were the conditions I was worried about a week ago, but everyone on board seemed to be enjoying the very active sailing we were doing.

After a few hours of strong winds, occasionally drenching downpours, and a bit of bouncing around, we tucked in behind Little St. James island to pick up the lunch I’d ordered from Pizza Pi, the only pizza shop on a sailboat that I’m aware of anywhere in the world. When Darby and Mia pulled the tender back up to the stern of our catamaran loaded with pizza, they received a hero’s welcome that rivaled the parade Boston threw for the ’04 Red Sox (at least in enthusiasm if not size).

No rain... no rainbows

Now the boat is back at the dock, Art, Victoria, and the rest of the crew are resting up on St. Thomas, and I’m flying to Charleston to start the next adventure. I’ll miss the Islands, but am excited about what’s next.

If you would like to join us for our next BVI Sailing Expedition, check out for information on trip dates, rates, and to reserve your cabin today. (As of March 31, 2022 the site is uploading to the web, so it may take a day or two to show up. Thanks for your patience.)


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