The first time I anchored in one of Jost Van Dyke’s perfect natural harbors, our boat shared the anchorage with only one other, a small, privately owned sloop.

When I returned to the British Virgin Islands in January 2024, our chartered 50-foot catamaran shared Jost Van Dyke’s Great Harbour anchorage with roughly 25 charter boats and, at the harbor’s outer edge, a 247-foot superyacht painted in an iridescent mix of green and turquoise.

Think the BVIs have changed?

My introduction to these splendid sailing waters occurred so long ago that The Moorings, now a giant of the worldwide bareboat charter industry, was still in its formative years in modest quarters on Tortola. Its founders, Charlie and Ginnie Cary, graciously escorted us to our rented monohull sloop.

I’ve been back a few times since then, and noted incremental changes as ever more sailors discovered this gem of the Caribbean, but I wasn’t ready for what I saw on this cruise, starting with that green monster at Great Harbour. 

I always pegged fellow BVI charterers as kindred spirits, sailors on holiday away from the jobs that pay for their fiberglass sailboats at home, soaking up a refreshing dose of trade wind breeze, Mount Gay rum and Jimmy Buffett on their rented boats.

Thanks to my in-depth research during the latest visit (which, of course, was work-related), I can report that quaint image is obsolete. Some of my fellow BVI charterers in January paid more than a million dollars to rent their boat for a week.

That’s the going rate (actually $1,076,500 plus the six-figure tip for the crew of 23) to charter Kensho, the green superyacht anchored at Jost Van Dyke.

Kensho is the biggest and most over-the-top palatial, not to mention most imaginatively painted, vessel in a small fleet of chartered oligarch-class motoryachts cruising in the Virgin Islands.

Boat-watching at cocktail hour has long been one of the amusing pleasures of BVI cruising, but with the advent of rentable moorings, anchor follies (dragging and lots of yelling) are no longer reliable entertainment. That void was filled one afternoon at Bitter End with a show of ship-handling skill put on by the captain of one of those mega motoryachts. In a tight space a stone’s throw from anchored charter boats, he executed a perfect Med moor, nestling the stern of his 202-footer a gangway away from a small dock.

Kensho is too big for a feat like that, but no worries, its “guests” can be whisked to shore in a 30-foot Steeler Limo Tender that looks like a small version of the mothership with a matching paint job.

I’m guessing, though, that there’s not much incentive to leave Kensho to sample the native culture on shore. The yacht’s accommodations include four elegantly decorated decks connected by an elevator and spiral staircases, and for the athletically inclined, a gym, a swimming pool and what the charter agent calls a “beach club.” It was built in Japan in 2022 at a cost of $110 million. Maybe a million bucks a week is a good deal.

Speaking of big boats, did you know cruise ships now frequent BVI waters? Of course you did. They have been around there for some time, but they seem to be more numerous and more outlandishly outsized than ever. Passing one close aboard on a relatively tiny 50-foot sailboat is the marine equivalent of riding past blocks of skyscrapers in a New York Uber.

It’s selfish of sailors who have the skills and wherewithal to cruise in chartered yachts to resent sharing the BVIs with folks vacationing on cruise ships, right? Well, that’s probably the right thing to say, but when you hear stories about the Baths on Virgin Gorda being overrun on some days by hundreds of people bussed in from cruise ships, political correctness doesn’t come so easily.

On the bright side, it’s still easy to escape the madding crowd. A particularly enjoyable way to do that is on a catamaran, which has become the most popular charter-boat type in the BVIs. These cruising multihulls are loaded with accommodations that would be at home in a swank summer cottage, which is great for living aboard, but not so much for spritely sailing. It takes a good bit of breeze to get them going. So you could say they were made to order for the BVIs.

The famed winter winds were in full force during our cruise—often more than 20 knots from the east—and the big cat loved it. I’m not saying it flew a hull or delivered any surfing thrills, but on a wonderful jaunt from Leverick Bay to Anegada the boatspeed topped 11 knots.

The cat had a more than ample spread of sail area, most it in a full-battened Dacron mainsail with a generous roach. Other charter catamarans in the BVI have less sail area, as in none. Cruising catamaran powerboats are another of the new wrinkles in the BVI. No problem there, but it seems a waste of perfectly good wind to me.

I should mention that superyachts, cruise ships and power cruisers aren’t the only manifestations of change in the BVIs. 

For example: the Soggy Dollar Bar on Jost Van Dyke. Once an island outpost on the shore of White Bay, it was known mainly to the sailing cognoscenti, reachable by dinghy from an anchored yacht when the swells are not too aggressive or by jitney of dubious roadworthiness from Great Harbour over breathtakingly steep hills, it’s now an entertainment destination. On a weekday afternoon, it was overrun by daytrippers delivered by high-speed center-console powerboats and bent on Painkiller partying.

I’m just reporting the changes in the  BVIs, not judging them, because they don’t really matter. What does matter is that this compact array of islands, graced by pretty anchorages, blessed by the tradewinds, remains one of the best places in the world to cruise under sail.

On the penultimate leg of our cruise, a broad reach from Bitter End to Great Harbour, as waves building in a hardy breeze curled behind the surging cat, I looked aft and beheld a panorama of indigo seas crested in brilliant white—and was glad I was not seeing it from the top deck of the Kensho.