Boats anchored off two distant strips of white sand beach are the only signs of civilization you see when sailing to the island of Jost Van Dyke. One, White Bay, to the east, and the other, Great Harbour, to the west. Both are meccas for cruisers and day trippers who want to immerse themselves in the quintessential Caribbean vibe and heady beach bar culture of this British Virgin Island. It was certainly why we came. After all, what better way to celebrate my father’s 90th birthday, and have him happily retrace steps made some two decades before, than with an ice-cold painkiller and comical conversation with the island’s famous calypsonian Foxy Callwood. Yet there is much more to Jost Van Dyke than rum and ribald tales under the palms.
Jost, as it’s often nicknamed, measures three square miles with some 300 residents, the smallest of the four main BVI’s both in size and population. Line of sight sailing is the norm as the island is a mere five miles northwest of Tortola and five miles north of the U.S. Virgin Island of St. John. The quaint customs and immigration station is located right on the beach at the head of the main dock in Great Harbour. On weekends and during the winter season, a vendor sells fresh-baked goodies from Christine’s Bakery at an umbrella-topped table just off the dock. The cinnamon sweet rolls are delicious, so is the coconut bread and carrot cake, plus local fruit drinks like passionfruit punch.

Great Harbour
The mile-long beachfront in Great Harbour is lined with over half a dozen beach bars and shops. There’s Ali Baba’s, Corsair’s, Rudy’s Mariner and of course Foxy’s Tamarind Bar as well as the Jost Van Dyke Scuba Shop. The ambiance is suitably sleepy until late morning when the bars open and dishes like local lobster start flowing out of the kitchens. Foxy’s is the best place to check out the wacky atmosphere that’s become a sight-seeing stop unto itself. That is, the myriad of business cards, burgees, license plates, posters, and outer and under clothing that adorns the bar’s inside roof. It’s definitely a showpiece.

White Bay
It’s an easy walk from Great Harbour east and up over the hill into White Bay. The day boats from St. Thomas, family cruisers from Puerto Rico and occasionally cruise ship excursions keep the waterfront here hopping (i.e. crowded) from about 10am to 3pm. Before and after this, it’s lusciously laidback. The most famous spot is the Sand Castle, home to a small resort made up of six cottages, a tiny restaurant and the six-seat Soggy Dollar bar. The Painkiller – a blend of rum, pineapple juice, orange juice and cream of coconut served over ice with a sprinkle of fresh nutmeg – was reportedly born here in the 1970s.

Diamond Cay
The east end of the island is harder to reach. From White Bay or Great Harbor, it’s about a 40- to 50-minute walk on paved roads past Little Harbor and its seaside restaurants, to Diamond Cay. The drive, by rental car or taxi, is an easy ten minutes. Either way, the road cuts up along the hillside with gorgeous ocean views stretching to the fellow Virgins beyond. By boat, it’s less than an hour sail from Cane Garden Bay on Tortola to the dock at Foxy’s second restaurant, Taboo, or moorings out front. The real highlight here is the Bubbly Pool, a natural tidal pool that indeed bubbles effervescently as waves from the Atlantic come crashing through the rocks. This is an idyllic spot in good weather, but can become dangerous when the surf really kicks up.

Jost is a great destination to visit anytime. It’s even more special when there’s a local event. New Year’s Eve is the biggest celebration of the year. Full moon parties happen monthly at several of the beach bars. Finally, sailors will especially enjoy when the West End Yacht Club on Tortola hosts its Foxy’s Wooden Boat Regatta in May and Foxy’s Cat Fight in October. Mark those dates on your calendar!