If you’re not one of the superrich yourself, then an encounter with the superrich can be confusing. I had such an experience recently, when I accepted an invitation for a wine tasting on a winery owner’s boat on the San Francisco Bay. I pictured huddling in the wind on a small sailboat, sipping Chardonnay under the Bay Bridge. So I invited my brother-in-law Mario, who also happens to be my number one wine-tasting partner, and we both brought extra flannel shirts and old fuzzy jackets. On the drive over, we talked about world-critical matters like home-job buzzcuts, done with electric hair clippers, and how they look when they grow out long—which is where we both stand currently, in terms of hair. (The answer: It looks ridiculous; hair styling is a legitimate profession.) We both have two-year-old daughters, so we talked about them as well.

But then we arrived at Pier 40, next to the baseball park, and got a look at the boat: Called Silverado, it was in fact a positively enormous pleasure yacht, appropriate for Jackie Onassis or Rupert Murdoch. Walking out on a long dock, we ascended a gangway and stepped into a huge party space at the boat’s rear. The room took up perhaps one-third of the total floor space of that deck, and there were decks both above and, presumably, below us. A shipboard phone roster, posted on the wall, showed perhaps 15 on-board rooms distinct enough to merit their own, separate phones. Distinct enough, as Mario put it, that you wouldn’t just want to say, “Hey, bro! You in there?” You’d want to use a phone.

The room was filled with guests tasting wines, hors d’oeuvres were already hitting a nicely laid table, and there were several expensively dressed women around. The owner of the yacht—and of the winery, Brassfield Estate—is Jerry Brassfield, a trim, fit, 50-ish guy with freckled skin and a gleaming bald head and on this night a beautifully tailored sport coat paired with slacks and a tie. Jerry apparently made his millions in vitamins, and Mario, who learned this detail for us, loved it. Mario loves the freakish specificity of human lives. Vitamins! Looking around the boat, at the dazzling display of wealth, Mario quipped, “The man clearly has a B complex.”

Brassfield lives most of the time, we were told, on the peninsula south of San Francisco, and he has a full-time boat staff that moves the yacht to Alaska for the summers and then on down to Baja for the winters—migrating, as it were, like gray whales. Except only sort of. Because the idea is that the yacht will be wherever Jerry wants it when he’s ready to pass time on its glorious decks. Then he’ll pop out in his private helicopter.

More to the point: In addition to all this material splendor, Jerry also owns a 2,200-acre cattle ranch in Lake County, California, and he’s been making wine there since 2001. And this is where things became confusing for me. I love Lake County. That is exquisitely beautiful country, and an underappreciated part of California—not just for winemaking. Lake County is also underappreciated for the quiet, rustic beauty of its dry hills and summer-golden grasses. Deer are plentiful in those hills and hollows, mountain lions leave their big prints on the dusty dirt roads, coyotes probably outnumber dogs, and bobcats are a common sight. I liked Jerry’s wines, too—especially his reds. This is a guy making a serious push toward serious wine. Jerry was a gracious and warm host. So were his lovely wife, and his tall, poised daughter.

But I found all of this bewildering: It’s hard to get a clear read on the wine you’re tasting when you’re tasting it in those surroundings. On the other hand, we always taste wine in one surrounding or another, and wineries sure go a long way to create a particular experience—witness all those grand Napa wineries with their massive and silly castlelike buildings. Walk around one sometime, and you’ll be struck by how utterly empty much of the space feels. The reason is that there’s simply no purpose for such grandiose architecture, except for the visual impact, the feeling it’s meant to give you about the wines you taste there. To be clear: Jerry Brassfield has hired a good winemaker from Rutherford Hill, he’s using the best soil consultants in the country, and he’s making a Cabernet with a pleasant tannic backbone and dense jam and spice flavors; he’s also making a rich and smoky Syrah with tobacco and even body musk in the nose. So I guess what I’m saying is that when I think of a Syrah and a Cab from a remote cattle ranch in Lake County, I think very rustic and positive thoughts; and when I taste that wine aboard a spectacular pleasure yacht, glimpsing the life of a megamillionaire, squinting at the sun off the white deck and the glitter on the arms of the women and the heartbreakingly beautiful views of a San Francisco Bay I so dearly adore, I have feelings I can’t entirely sort out. A disconnect, maybe? A wonder what it’s all about? What it all means?

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