Virginia's Cabs and Chardonnays aren't household names—but they should be. After decades in the shadow of Napa and Sonoma, this overlooked wine destination has blossomed, with superb vintages and restaurants to match.

My guest room was impeccably tasteful, with its hand-carved mahogany bed dressed in crisp white Italian linens. Outside, gray mist hovered over green hills laced with vineyards, painting a portrait that could rival any view in Tuscany.

But this wasn’t Italy, it was Virginia, and my hotel was the passion project of 31-year-old Eric Trump, the president of his namesake winery just next door. As a writer with a world of wine country options to choose from, I was still a little surprised I was here. Virginia was a place I had put on the back burner. I’d do a tasting of its wines up in New York and find them iffy (and, full disclosure, sometimes they still are). But the buzz kept building, and savvy insiders had been telling me good things. I finally decided to drive down and experience the destination for myself.

The logical place for me to start was with the most famous (not to mention controversial) name in the bunch. I spent a day sampling Trump’s standout Chardonnays and a sparkling 2009 blanc de blancs, full of pure apple flavors, all made by the ambitious young winemaker Jonathan Wheeler, and it was clear that the state had arrived. “Virginia is on the warpath,” says Eric, Donald Trump’s son and the force behind the 1,300-acre estate. “We have 275 wineries, and are finally winning gold medals in competitions.” Katherine Wolkoff

The crusade to put Virginia on the wine map stretches back to Thomas Jefferson. For years, aspiring vintners planted classic European varieties like Viognier, Cabernet Franc, and Cabernet Sauvignon. But loving a craft doesn’t mean you’re necessarily good at it, and mastering the terroir—humid summers, rocky earth in one place and clay in another, not to mention the occasional hurricane—took time and effort. (Burgundy, for example, has had plenty of time to figure out the elements.) During the past few decades, a handful of talented winemakers—two Italian expats, in particular—have been experimenting with various grapes in various soils, and slowly gaining ground. Today, thanks to these veterans, their pupils, and some talented newcomers, there’s now a critical mass of excellent wines being made. The action is centered in two places: the Monticello American Viticultural Area (where the Trump Winery is located, less than three hours southwest of Washington, D.C.) and the northern Virginia region (roughly an hour from the capital). Katherine Wolkoff

Much of the success is a testament to the area’s openness to outsiders. In 2011, the Trumps began buying up pieces of Patricia Kluge’s bankrupt estate, and got it for a $16 million song. They poured even more resources into the already state-of-the-art facilities. (Kluge herself had short-lived success with her own wines.) This spring, her 26,000-square-foot mansion—done in a lavish, neo-Georgian style by the legendary interior designer David Easton in 1985—was converted into Albemarle Estate, a 10-suite boutique hotel. It has a pool, a movie theater, and a poker room, among other amenities, all left over from the Kluge days and newly restored. And yet the place doesn’t feel stuffy— just like the region itself.

Virginia’s ace in the hole has always been its lush terrain, good for growing almost anything and lovely to look at. And since vineyards are still a relatively rare sight, the scenery isn’t stuck on repeat. This is horse country, and the landscape provides subtle variations on the rural theme, making it ideal for a driving trip. I kept track of the quirky road names—Possum Hollow Lane, Pinch ’Em Slyly Place—as I drove around, surrounded by white fences, with the foothills of the Blue Ridge Mountains for a backdrop. “We have the natural beauty, plus that Southern charm,” said Kerry Woolard, the general manager of the Trump project. “People talk about ‘sense of place,’ and that’s definitely here.”

Part of that power derives from the destination’s role in American history and, indeed, American wine history. When Woolard mentioned that Monticello, Thomas Jefferson’s grand domed mansion, was only seven miles north, I set off to discover a bit about our country’s first legitimate oenophile. A notorious bon vivant and big spender, Jefferson returned from Paris in 1789 carting 680 bottles of the best European vintages. He eventually tried (and failed) to grow grapes at Monticello. Katherine Wolkoff

Gabriele Rausse, an Italian by birth and the director of Monticello’s gardens and grounds, walked me around the stately, Neoclassical landmark, even taking me to Jefferson’s original small brick cellar. “He didn’t live long enough to finish all his experiments,” Rausse said, a little wistfully, as we stood on a hillside next to Sangiovese vines growing right where Jefferson had planted the same grape.

Rausse is one of the founders of the modern-day Virginia wine movement. He immigrated here in the 1970s, becoming the head of Barboursville Vineyards, a 1,000-acre estate just 20 miles from Monticello. Back then, his experiments with classic European grapes like Riesling met with skepticism from locals (“people said the future was in tobacco,” he recalls, laughing). But the naysayers were proven wrong. Barboursville is currently one of the state’s top-tier producers, and sells about 38,000 cases a year. Rausse has long since left, and Barboursville is now in the hands of the equally charming Luca Paschina, a fellow Italian who has one of the best long-term track records in Virginia. All of Paschina’s wines are excellent, but you don’t want to miss his ethereal Vermentino Reserve and elegant Cabernet Franc Reserve, the latter made from the area’s most reliable, utility-infielder red grape. Katherine Wolkoff

At Library 1821, Barboursville’s weekend tasting room, which is an enclosed neo-Palladian loggia, Paschina and I snacked on house-made bresaola and sipped his high-end Bordeaux blend, Octagon, while discussing the new generation. “Due to the presence of talented young winemakers from the West Coast, Europe, and South Africa, there are better wines being produced in Virginia,” he said. Like many regions outside of sunny California, Virginia has real vintage variation because of its climate, and it’s important to pay attention to those numbers on the label: 2010, 2013, and 2014 are noteworthy years. “Two out of ten vintages are more challenging, but Piedmont, Italy, where I’m from, is not much different. The last I heard, they’ve done pretty well.” Katherine Wolkoff

If the tasting room at Barboursville has a formal atmosphere, the one at Michael Shaps Wineworks, just a few miles from Trump, is more unplugged. Past a foxhound-breeder’s business, at the end of a long and unpromising gravel road, sits a sign to reassure visitors: YOU ARE IN THE RIGHT PLACE!

Shaps is an industry veteran who also makes wine from some of the best vineyards in Burgundy. Many of his Virginia wines follow the Burgundian négociant approach, blending grapes from different plots, instead of the “estate” model that prevails here. Both Shaps and 39-year-old winemaker Ben Jordan (who just left, amicably, for a new gig at the nearby Early Mountain Vineyards) have enjoyed the flexibility that comes with buying other grapes to get the best of what’s out there. “The future is wide open,” Jordan explained when I showed up one hot afternoon. “You can outgrow your estate.” Michael Shaps Wineworks feels like a breath of fresh air, from the sleek design (corrugated metal reclaimed from a tobacco barn lines the walls) to the millennial-friendly growler program. It costs $10 for a 64-ounce glass jug, which can be filled (and refilled) with their Mon Bidon red, white, or rosé for a mere $25. All that American history isn’t weighing down innovation.

A similar attitude can be found among the chefs and restaurateurs in Charlottesville, a natural stopover in the Monticello AVA. It has the refined yet raucous atmosphere distinctive of most college towns; experimentation is not only welcomed but expected. Last fall, the dining scene got a youthful jolt when four friends—Mitchell Beerens, Ian Redshaw, Andrew Cole, and Loren Mendosa—opened the Neapolitan pizzeria Lampo, a hit with University of Virginia students. “We used to go to D.C. for decent pizza,” Beerens jokes. The foursome personally lifted off the building’s roof to install a three-ton MG Forni oven, which had been shipped from Naples, and even raised money for the meat slicer on Indiegogo. The pies? Perfectly blistered.

“Charlottesville has pretty killer food,” said 36-year-old Daniel Kaufman as we shared a dozen Black Bear Point oysters at his restaurant, Public Fish & Oyster. This casual, exposed-brick spot, which focuses on seafood from the East Coast, has been packed with residents and tourists since its opening a year and a half ago. Like many local places, it also features some Virginia wines. (A moderate $20 corkage fee also encourages customers to bring in area bottlings.) “Young people are getting into the mix. It’s competitive, but we respect each other. I borrow sugar from my neighbors—and that’s not a metaphor.” Katherine Wolkoff

Proving the point, Kaufman directed me across West Main Street to Gearharts Fine Chocolates. The co-owner, Tim Gearhart, was a cook in the Marines before opening his two-story shop in 2001. Students and their well-heeled parents gave the business an immediate boost, which eventually led to national recognition. But the whole operation still feels mom-and-pop. Gearhart and his team handcraft each chocolate, using ingredients like cracked pepper, balsamic vinegar, and Cabernet Franc—sourced, naturally, from local producers like Barboursville.

After a couple of nights, I left Charlottesville behind for northern Virginia, a region just two hours north but with very different growing conditions. Arriving at Linden Vineyards, I could see right away what was different: the soil. Unlike Monticello’s signature red clay, the terrain here is rocky—ideal for planting Cabernet Sauvignon. That’s why winemaker and proprietor Jim Law calls one of his bottlings Hardscrabble, and it’s arguably Virginia’s best Cabernet blend, ripe with black-currant flavor.

Law has been working this land, which he bought in 1983, for most of his adult life. “It took us 15 years to figure that out,” he told me, pointing at the tighter spacing of the vine rows, a seemingly minor detail that is helping him achieve better results. “I’m making wines for top tasters and sommeliers. Money’s a little tight, but I can’t imagine doing anything else.”

Rutger de Vink, the Dutch-born founder of RdV Vineyards, some 13 miles east, once worked under Law, and matches his mentor’s level of devotion. “We’re no longer hobbyists,” he says, preaching Virginia’s progress as gospel. Spokesmodelhandsome, with a thatch of wavy hair, de Vink has won over critics with two richly textured, small-production Cabernet blends. Katherine Wolkoff

From afar, de Vink’s winery looks like a white clapboard farm, but inside it’s thoroughly modern, and the “silo” is actually a James Turrell–like space that glows at night. Instead of a bland, cavernous tasting room, he’s installed an intimate salon decorated with Eames chairs where you can sample both of his premium Cabs. You’d imagine de Vink living in a glass house, but the reality is even better: he bunks with his two children in an Airstream trailer in the vineyards. “I love the land,” he says. “It’s a way of life.”