I was sprawled on our flybridge in a quiet cove in the British Virgin Islands, gazing at the brilliant stars dotting the black sky, when suddenly I wondered if a young sailor, perhaps on the verge of raiding a treasure galleon lumbering down the Spanish Main, had watched these very same stars from this cove and hoped he would survive to see another night.
So much would have been the same: the tug of the anchor in the warm trade winds, the smell of the damp island, the soft sound of waves shushing onto a sandy beach.
But I had satellites in my night sky. My companions, sharing rummy drinks with clinking ice, delighted in pointing out each one as it slid across our velvety sky.
The BVI are arguably as much of a dream destination as the volcanic peaks of French Polynesia’s Mo’orea for trawler skippers, and much more accessible to those in North America. The BVI also have become a bareboat mecca because of the generally calm waters, line-of-sight navigation and well-marked hazards. For most skippers, the worst thing to befall them is a regretful morning after one too many Painkillers at Foxy’s sandy-foot pub on Jost Van Dyke.

Centuries ago, these waters were frequented by Spanish galleons and the pirates who preyed on them. Today, you’ll find tiny Dead Chest Island (yo ho ho and a bottle of rum!) as well as a cave at Norman Island (supposedly Robert Louis Stevenson’s Treasure Island) whose treasure is no longer hidden gold doubloons, but squadrons of brightly colored fish that peer into your snorkel mask.
Sir Francis Drake Channel runs the length of the BVI, protected on each side by delightful islands, just as New York’s Times Square has attractions left and right. Tortola is both the main port of entry for yachts as well as home to the international airport. It’s where boaters will find supplies and repairs, and it’s the base for many of the charter companies.
The usual routes to explore the BVI are so well traveled that I’m surprised there isn’t a rut in the sea to follow. Go clockwise or counter—the choice either way is great.
A favorite first night is at Norman Island, if only to dream of gold in the swimmable cave, but the spot also has the Willy T, originally a pirate-ish ship that was lost in a hurricane and now revived as a floating nightspot for wild jumps from the upper deck powered by alcohol. Moor far away if you plan to sleep.
Hurricane Irma in 2017 trashed the BVI, but spots like The Indians (off Norman Island) and the wreck of the mailship Rhone (off Salt Island) remain for snorkelers and divers alike. And it would take more than a mere hurricane to change The Baths, a pile of boulders seemingly tossed by a giant to create eerie caverns and pools to explore.

The famed Bitter End Yacht Club on Virgin Gorda is making a comeback, now as a marina and soon with its yachtsman’s restaurant and lodgings. This is the jumping-off point for Anegada, the farthest of the BVI at 15 miles away. It draws skippers for one thing: buttery lobsters.
Jost Van Dyke, named for a pirate, is notable for beach bars like Foxy’s and Soggy Dollar (from swimming ashore, right?) with island food, potent potables (Foxy’s Firewater Rum is well-named) and good anchorages. Nearby Sandy Cay is everyone’s vision of a flawless tropical island: palms, sandy beach, no civilization and warm water.
Heading back to Tortola, either to reprovision a trawler or return a bareboat, don’t miss Soper’s Hole, now recovered from Irma with colorfully cheerful buildings. Have conch fritters at Pusser’s, and wash them down with Bushwhackers (don’t say we didn’t warn you!) while you start planning a return to the BVI.