The Dominican Republic is known for its hot beat, "béisbol," and mega-resorts. But far from the crowds, Karl Taro Greenfeld explores colonial haunts, untamed nature—and some of the caribbean's most magical beaches

It's beginning to look like this wasn't such a great plan after all. At the rental car office at Santo Domingo's Aeropuerto Internacional Las Américas, my wife and I fill out the requisite paperwork and test-drive several vehicles, which turn out—for reasons ranging from missing seat belts to burned-out headlights to fumes suspiciously redolent of burning transmission—not to be our idea of appropriate transportation for two weeks of road tripping with our two small daughters. Our standards are modest—four wheels, locking doors, operable windows, working headlights, a trunk—yet the curiously named Stalin Guzmán finds it beyond his means to produce such an automobile. As for the rest of the rental office crew, they stand by in their white shirts with a jaunty logo ironed over their hearts and, in an occasional frenzy, wipe down the variously malfunctioning cars with wet rags. We have been in the garage or inside the air-conditioned office for two full hours when my wife, Silka, finally flies into an undignified rage, going on about how we have children, how we have wasted two hours, how it is inconceivable to her that the company actually cannot produce the fully functioning automobile which we reserved weeks ago.

Stalin looks at her, shakes his head, and nods. "I know. It's terrible. Can you believe it?" he says, as if he is suddenly on our team, which leaves us and Stalin against those guys with the rags, and without Stalin on their side, these proletarians are such a forlorn bunch that it is hard to keep the pressure on. So we go with Stalin back to the lot, where we choose yet another vehicle, a four-wheel-drive Suzuki, which, when we rub the dust away, turns out to be dark blue. At that point, if it runs, if it has seat belts—forget it, all I want is good running order; we can somehow improvise restraints—then we are renters. Stalin turns the key, starts that baby up, and says he will get the workers to clean it.

"How long will it take?" I ask.

And Stalin proclaims, I swear to God: "I have a five-minute plan."

Our own plan, devised by Silka and me as we studied a map of the Dominican Republic spread out on our dining room table, is to drive north from Santo Domingo, the capital, through the middle of the island and then head east, to see what lies at the end of the road. Too much of the Dominican Republic is overlooked by its 3.7 million annual visitors—it is currently the most popular destination in the Caribbean—who mostly head straight for the golf courses of Casa de Campo or for the monstrous, cocktails-with-little-umbrellas-in-them resorts of Punta Cana, along the eastern coast. We want to seek out those secluded beaches, lush mountains, and perfect little hotels that don't make the package-tour itineraries.

I've always marveled at how the four-hour flight from New York to Santo Domingo seems too short to bridge the vast distance between the two worlds. The Dominican Republic has occupied various niches in the American imagination: sugar and slave way station, rum port, tax-exile hideaway, banking resort, Caribbean bulwark against Castro, and, most recently, baseball superpower. It was too big, too poor, and too rowdy for those who wanted nothing more than a rum punch and a steel drum band. Then, during the 1990s, the Dominican Republic built the most extensive resort infrastructure in the Caribbean. It has now become easier to fly into the D.R., take a bus to your hotel of choice, and never step off the resort grounds than it is to mix and mingle with Dominicans and take in a little local action.