An up-close view of the flock of flamingos, reintroduced to the island from Bermuda in the 1990s after they’d been hunted to extinction on Anegada, was elusive, but we spotted them through a telescope at the lookout over the salt flats that dominate the interior of the island. What was not elusive was the absolutely stunning crescent beach on the windward side of the island. Between the white sand and the rolling waves beyond the reef and the always perfect 80-degree water, this ranked among the best beaches we’d ever visited. Despite trying a couple different spots, the snorkeling was a disappointment and the reef was noticeably degraded since our last visit when we swam among eagle rays. 

The water was too lovely to stay out of despite the lack of sea life, so we enjoyed the swim while Monica at the Flash of Beauty Bar made rotis that we enjoyed with icy cold Carib. The business relies almost exclusively on charterers who make the trek to the other side of the island, she said, and that day it was just our group and a carload of Australians who happened upon the understated but charming spot. Blissfully, we had the beach all to ourselves. It was a more raucous scene down the beach, Tipsy’s by Ann and the Cow Wreck Bar were happening spots, with happy revelers enjoying cocktails in the water.

With a day and a half of land-based adventures under our belts and our fill of Anegada lobster, we set sail back to Virgin Gorda, another opportunity to enjoy a passage, this time with less breeze, a touch more forward. Our destination was Bitter End Yacht Club, which we wanted to check out after a sizable rebuild—still in progress—following utter devastation after the hurricanes. While the cottages have not yet been rebuilt, the main parts of the club are beautiful, shiny and new. The mooring fee includes the use of the showers and heads at the club.

Not long after we picked up a mooring and enjoyed a swim—a mandatory daily activity as it would be a tragedy to let the beautiful water go unenjoyed—Jim and his companion Drake, a stray dog that showed up one day and decided that co-captaining a RIB in North Sound seemed like a good gig, swung by to offer frozen concoctions. Jim started Rum Runner BVI, which also carries Cuban cigars and logo shirts for the enamored, two years ago.

“I kept coming down year after year, and finally I just stayed,” he said. “The first year in business I sold 19,000 drinks.”

We had one last big sail planned, and it delivered everything we would need to sustain ourselves until sailing season returned in our northern climate. The next morning we headed out of the channel, set the sails and headed down on a broad reach 25 miles to Jost van Dyke. The breeze was up again but with the favorable angle it was easy sailing with something that felt like a precursor to surfing, if such a cat were capable of it. 

We jibed out early on, a tactic that had the added benefit of picking up a bit of time on the “competition” we’d spotted on our same course. Behind us, whitecaps covered the sea, which had taken on a dark blue hue. In the distance we saw St. Thomas about, well, 20 miles west, bringing to mind the sailing adventures rooted in Jimmy Buffett’s tunes of old. We jibed a couple more times, nothing on our agenda other than the pure joy of sailing.

Slipping past Sandy Cay—a 14-acre island owned by the BVI National Trust, where turquoise water laps up to a perfect beach—we doused the sails, and picked up a mooring in Great Harbour, intentionally positioning ourselves a bit farther from Foxy’s, which we knew would be abuzz with a great time being had by many later that night. The first step was grabbing a taxi, which seemingly materialized out of nowhere when Darryl, the first person we spoke to when the dinghy hit the dock, brought his truck around and delivered us to the Soggy Dollar Bar in White Bay, less than a mile as the crow flies, but accessible on foot only by traversing steep hills on skinny roads with hairpin turns. 

The Soggy Dollar and another favorite stop which had been known as Ivan’s Stress-Free Bar—a delightful self-service shack full of colorful characters and mostly cold beer—have a new shine to them that’s not entirely welcome. The problem with charming old beach bars is that when a hurricane takes them off the map, you can’t bring back the beach shack. That’s the kind of patina—both figurative and literal—that comes with age, and that process has started over. It was clear from the throngs—and thongs—arriving on powerboats from Tortola’s Soper’s Hole and other unknown destinations that the mystique of the Soggy Dollar was all the draw they needed, even if the place looks and feels much different. 

It’s practically a contracted requirement than when on Jost van Dyke one must have a painkiller, and while the Soggy Dollar Bar might have changed, we could attest to the painkillers still being the best in the world.