At Bloomberg Pursuits, we love to travel. And we always want to make sure we’re doing it right. So we’re talking to globe-trotters in all our luxury fields—food, wine, fashion, cars, real estate—to learn about their high-end hacks, tips, and off-the-wall experiences. These are the Distinguished Travel Hackers.

David Duncan is president and chief executive officer of not one but three Napa vineyards. He runs Silver Oak, which was co-founded by his father, Ray, in 1972. Renowned for its cabernet sauvignon, it counts Oprah Winfrey, LeBron James, and Matthew McConaughey as fans.

Duncan also presides over Twomey, a family passion project created by Ray, David, and his brother Tim in 1999; the winery specializes in merlot, sauvignon blanc, and pinot noir. His family also recently oversaw construction of Silver Oak Alexander Valley in Healdsburg, Calif., which was just named the first new-build LEED Platinum production winery.

Duncan doesn’t tally his annual mileage—or his elite tier. “I have no idea how many miles I fly per year, because I fly all kinds of different airlines,” he says. “And so I’ve become agnostic in terms of my status.” His favorite, though, is Southwest Airlines, where he always buys the same ticket (Business Select) so he can board early enough to sit in the same seat: the exit row 11F. “I like that the experience is always the same thing, it’s efficient, and the people smile.”

He lives in Napa Valley with his wife, Kary, a dermatologist, and their three children.

In a hotel you can earn unofficial VIP status with a single gesture.

Always order a bottle of wine you don’t plan to finish. When I’m staying somewhere for a couple of days, I’ll sometimes order a bottle of wine from the hotel restaurant with dinner. Then I only drink a couple of glasses and give the rest to the staff, since I know you’re close to the price of a bottle on three glasses anyway. Servers and sommeliers appreciate the gesture, and they tend to treat you like a VIP for the rest of your stay. Often I’ll get in late when I come to New York, and so I’ll have dinner at the hotel. And if you leave them some wine, then the next day they come down and everybody in the restaurant is like, “Good morning, Mr. Duncan,” and they know who you are. You just get a little extra. It’s better than a tip, because it’s something different and unique.

A certain souvenir will become a gift that keeps on giving.

I was raised in Colorado, so I learned that if you’re in a vehicle, if you’re outside, you wear sunglasses. And eyewear is the souvenir that keeps on giving: Eyeglasses are one of the coolest things to buy in other countries. They’re unique when you get them back home, and you get a lot of use out of them, vs. most souvenirs, which often become clutter. Relatively speaking, they’re not that expensive, either. A number of years ago, I was in Rome—on vacation, not working—for a week, and it was a bright, sunny day every day. So I bought a pair there, and they always make me think of that trip.

Staying fit and sleeping well on the road is simple if you follow this one rule.

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