St. Vincent
Credit: Matthew Wakem / Getty Images

More in touch with the Caribbean's pirate past than its ritzy present, St. Vincent sits a 400-mile close haul from the moneyed Virgin Islands and several decades of gentrification removed from subdued cruising ports like Sint Maarten's Philipsburg. The wild western side of the 133-square-mile hunk of igneous rock is fringed by black and white sand beaches that are empty but for the few travelers smart enough to book basic rooms in the jungle. The last truly Carib island – La Soufrière volcano wiped out the region's only remaining native community in 1902 – this outpost of sun-drenched lawlessness, where cultivating marijuana and brewing more-than-100-proof rum remain prominent cottage industries, draws a self-selecting crowd of boozy hammock swingers. The wild scene has earned St. Vincent a permanent spot in the hearts and livers of the leathery old sailors who drop anchor in protected coves like Willabilou Bay (now crowned by the remains of the 'Pirates of the Caribbean' set) and wander wild jungle paths.

The coming year will be big for St. Vincent: A new international airport with an expanded runway will allow more travelers more direct access to the island. Despite official assurances that the island has no interest in shaking off its come-as-you-are, donkeys-in-traffic vibe, the potential impact of more arrivals is hard to predict. Fortunately, St. Vincent remains more coconut water and less margarita. Regulars at Bush Bar in the aptly named Vermont Valley on the leeward coast make toasts amid frangipani and shout to the bartender in whatever language suits them. Snorkelers jump into nearby Cumberland Bay rather than booking day trips or guided tours.

Fifty miles northwest of Kingstown, the British protectorate's capital, where last-minute bookers can get a room for $75 a night at the gracefully aging Cobblestone Inn, a leftover of the colonial period, unpaved mountain roads weave around sharp peaks and volcanic rocks. One-bar towns like Chateubelair flow down the mountain like lava. On a road farther up the slope sits Richmond Vale Academy, a local school where travelers can book a simple room for $20. There, they can prep themselves for the climb toward the caldera to the north or a swim in the clear jungle river before thwacking down the road toward a black sand beach in flip-flops, nodding at the donkeys, schoolchildren, and rumrunners going the other way. 

More information: The easiest way to get to St. Vincent is on a sailboat from a more popular corner of the Caribbean. Barring that, jump on a Liat flight from Antigua.