Linger over long meals and learn from—and drink with—locals in the arts, architecture, winemaking, and more.

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To reach our lunch spot on the outskirts of Vila de Frades, a small wine town in Portugal’s Alentejo region, we walk through a yard with overgrown grass, fronting a single-story home with a terra-cotta roof. We creep through a low doorway into a dim room, where wooden shutters keep out the light—save for the sunshine beaming from our host. José Galante, a sexagenarian winemaker whose home we’re in, welcomes our motley crew of U.S. travelers with a big smile and a wave. He can’t speak English, but he’s clearly delighted to have us there. The room is kept dark for the sake of the traditional talhas, large clay urns filled to the brim with fermenting wine, lining the room; it’s an ancient winemaking technique that goes back 2,000 years and is only found in private homes today. On the other side of the room, he presents a welcome spread of fresh cheeses, bread, olives, and giant bowls of accorda, a warming soup. Over lunch I probably drink a little too much homemade unfiltered red wine (poured from ceramic jugs), and we probably stay a little too long (there are other things on our itinerary), but we’re having such a nice time, it seems silly to make an exit. Isn’t this how a vacation should be?

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It’s not necessarily how a vacation always feels. Traveling on a rigid schedule isn’t uncommon for North Americans, who have minimal PTO and often pack three vacations into one. But it’s hard to strike a balance between overly scripting a trip and going without any plans. That’s where Uncovr comes in. A tour company launched by California-based Jason Wertz in 2017, Uncovr takes small groups—no more than eight people—on tours with flexible itineraries, born of Wertz’s on-the-ground research in regions like Puglia, Alentejo, and Istria. 

The goal: to allow for a more organic travel experience, so guests never feel rushed or as though they’re on a flag-following, check-the-boxes itinerary. Trips don’t include big museums or in-demand restaurants, so it’s easy for the itinerary to shift if things don’t go as planned (which, let’s be honest, is inevitable on the road). During the days, Wertz himself drives us around in a van from art gallery to winery to local lunch spot. (When he picks us up at the airport, he immediately dishes out fresh, crispy pasteis de natas from the front seat.) Our plans include a number of outings that wouldn’t be possible without Wertz’s connections, forged by going and knocking on doors and meeting locals. On day three, we have a private tour of the Herdade do Freixo winery, ArchDaily’s building of the year in 2018, with the celebrated architect Frederico Valsassina. Afterwards, we drink wine together.

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That kind of access may feel reserved for the 1 percent, but Wertz just wants to connect people of all cultures and colors in a more intimate way. And once you meet the founder/operator/van driver, you realize he’s the reason these trips are possible. Wertz has a warm, gentle smile and easygoing way; it’s hard not to feel comfortable around him. He’s also deeply curious—part of the reason he’s managed to source so many interesting, creative hosts. “What better resource than the person who lives there?” asks Wertz. By cohosting tours with local chefs, designers, vintners, and artists, Wertz has managed to create the ultimate passion-led, local travel experience. “I think that’s where the designer in me comes out.”

In a past life, Wertz was a gallery owner, curator, and interior designer in Atlanta for nearly two decades—though he’s long been traveling with a creative’s eye. His mother studied art history at San Jose State University and led little Jason from Mexico to Italy and all over Africa. People would stare at Wertz’s mother—a white woman hauling her biracial child around—but Wertz says his mom was determined to celebrate diversity. “She was a person with a profound curiosity and appreciation for culture and art,” he says. She also wasn’t afraid to drive in a jalopy down to Mexico, he adds with a laugh.

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Creativity and design are strong threads that run through the journey, as is the desire to see more diversity in the travel space. “It’s through human connection that we break down artificial barriers,” says Wertz. “I know those barriers [like fear of the unknown] are out there, particularly for a traveler of color.” As the leader of all his tours, he believes change can come through storytelling—people sharing their experiences and getting out of their echo chambers. “Travel is one of the few platforms that allows for a cross-connection of people,” says Wertz. “We’re all pulling closer and closer to our little tribes, and I don’t know if that’s healthy in the modern world.”

As Wertz continues to grow his network of hosts, his curiosity and enthusiasm only deepen. In 2020 he will launch new tours in Tbilisi, Georgia, and Colombia, where he has spent weeks meeting with locals and tracking down interesting wineries, galleries, and hotels. In 2021, he hopes to expand to Japan and South Africa. “I spend an inordinate amount of time trying to find people who I think will have a special story to share,” says Wertz. “It’s like a treasure hunt for me.”  

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