Jost Van Dyke
"The hammock at White Bay isn't laziness. It's a philosophical position I've decided to defend."
The ferry from Tortola’s West End dock takes twenty-five minutes, which is not so much a journey as a state change. Jost Van Dyke has 320 permanent residents, approximately fourteen vehicles, one paved road running along the southern shore, and a reputation in sailing circles that far exceeds what any map would suggest is possible for a piece of land this size. I stepped off at Great Harbour feeling slightly overdressed for having worn shoes. Nobody around me was wearing shoes. I took mine off inside three minutes.

Great Harbour is a single arc of beach backed by a row of beach bars and essentially nothing else. The Soggy Dollar — named for the sailors who anchor offshore and wade in with wet wallets — invented the Painkiller cocktail, a combination of rum, orange juice, pineapple, and coconut cream that goes down with the deceptive smoothness of something that should be classified as a dessert. I had two. I recognized the danger. I ordered a third out of something resembling philosophical acceptance. Foxy’s, at the eastern end of the beach, is the other anchor: a bar decorated floor-to-ceiling with years’ worth of business cards and notes left by sailors passing through, covering every wall surface with the accumulated evidence of everyone who stopped here and, for a few hours at least, didn’t want to leave.

White Bay, fifteen minutes on foot over the hill from Great Harbour, is a different register entirely. Quieter, prettier in a more elemental way, with water the exact shade of blue that makes you feel the word “turquoise” was invented specifically for this particular afternoon. There is a hammock between two palms that I claimed for an hour and thought about everything and nothing in approximately equal measure. The food on Jost Van Dyke runs to grilled fish and conch fritters and johnnycakes that come out of someone’s kitchen window — unpretentious, excellent, and timed to whenever things are ready rather than whenever you’re hungry. This is not a complaint.
When to go: December through April for reliable trade winds and flat water. New Year’s Eve is legendary on Jost Van Dyke — hundreds of boats fill the anchorage and the beach bars stay open until dawn. Either the best night of your year or categorically too much, depending on your constitution. April through June is quieter and still beautiful.