The usual way to purchase wine at auctions is as follows: find a wine you’ve loved in the past, or something that multiple critics consider near-perfect, and keep bidding until that prized bottle is yours. 

But  there's an alternative to consider that involves much less time, and might actually result in you coming away with some real curiosities. Look for wines without scores, at modest prices, with significant bottle age, and a hint (but not a wealth) of pedigree. These aren’t wines to save for special occasions; they’re wines to open with guests as experiments that often turn out to be excellent dinner pairings. 

Of course, you’re going to run into some duds—that's inevitable when you’re playing this game. But you’ll often find yourself sharing and talking about wines that are more interesting, and often cheaper, than a new release of similar quality pulled off the nearest retail shelf.

Ready to flirt with this wine auction Twilight Zone? Not so fast, because bidding erratically is a quick path to disappointment. Despite the fact that I’ve spent quite a few years writing about wine professionally, I’ve found it necessary to stick to some core guidelines to keep my auction buys (mostly) sensible. 

These strategies have evolved over time, and I still run into an undrinkable bottle every now and then. But disappointments have become increasingly rare as I’ve added new rules to my playbook. Here’s how I find dusty, overlooked bottles that are worth drinking. 

Set a Price Cap

Online auction listings can be endlessly long, so the quickest way to narrow your options is to set a price cap. That puts your focus squarely on humble bottles that most bidders will simply ignore. Granted, if you set your upper limit at $50, an obscure bottle of some great producer from your favorite vineyard will almost certainly be listed at $51 and you might not see it. Ignore that feeling, and remind yourself that FOMO is one of our era’s most potent soul-killers.

Unless I’m looking for something specific, I then sort from oldest-to-youngest and scroll quickly until something catches my eye. 

Find a Spark of Recognition

I’m looking at auctions to find the oldest bottles that are both reasonably priced and potentially interesting. I’ve found it best to avoid complete unknowns and to stick to producers I’ve enjoyed in the past, or at least ones I recognize. The worst old auction bottles I’ve opened—dead, muddy, and actively spoiled—have generally been from defunct producers I’d never heard of before. 

One dynamic worth considering, particularly in the New World—many of the brands that are now large corporate entities were still independent back in the 1980s and ‘90s, and were making sensible, balanced, more-or-less artisanal wine.

Play Both Sides of the Vintage Chart 

Some vintages can do no wrong. For example, it’s hard to make a mistake buying 1991 Napa Cabernet or 2002 Champagne, but that’s also where the most well-heeled collectors will be hunting.

You can drink good wines from great producers at good prices in less heralded vintages. But the ultimate hack is a bit more complicated—finding the actual vineyards that were most likely to overcome a bad vintage’s biggest deficit. 

Hot vintage? Try to find wine grown on cool, shady hillsides (north-facing in the Northern Hemisphere; south-facing in the Southern). Cool and wet vintage? Look for wine grown on the rockiest, steepest, most sun-drenched spot you can find. In California’s often-panned 2011 vintage, for example, look for wines grown at higher elevations. Up above the fog that settles in coastal California’s valleys, ample sun and breeze plus well-draining volcanic soil helped keep grapes dry and healthy, despite a cool season capped by an early October deluge.

Push the Drinking Window 

Few American wine drinkers age their wines, even those that are made to age. As one Napa winemaker once remarked to me, tell someone visiting the tasting room that a wine is fresh, fruity, and drinking wonderfully today, and they won’t buy it. Tell them it’s massive and ripe and tannic and needs ten or more years in bottle, they’ll buy it and drink it that night.

Maybe because of this dynamic, winemakers tend to underestimate the longevity of their wines, particularly the humbler ones. They understand the realities of the wine market, that virtually no one is going to be drinking them 10 or 20 years from now. 

Case in point—I recently acquired a 1991 MacRostie Carneros Merlot. The back label suggests enjoying it “up to 10 years from vintage on special occasions with friends or family.” When I opened it more than 30 years later, it was still bright and lively. Which brings us to…

Check the Back Label 

That MacRostie Merlot was grown at Hudson Vineyard, one of the best situated and managed vineyards in Carneros. To know that, though, you’d have to move your cursor over to the back label image and zoom in. 

The older the vintage, the less information you’re going to be able to find about the wine in question. Today, it’s routine for wineries to upload an information-rich PDF for each of their new releases. In 1991, there wasn’t really an internet to upload to, and while wineries did document information about their wines, much of that information has been lost in ancient filing cabinets. 

Zooming in on a label photograph, particularly a verbose back label, can provide crucial data that might not be available anywhere else on the web (as long as you take any drinking windows you find with a grain of salt.)

Buck the Fashion 

Stick with producers and regions that have some potential, but also recognize that varieties come and go. The reputations of entire regions can wax and wane due to factors that have little inherent correlation with the quality of what’s in the bottle. 

Merlot, for example, was red hot in the 1990s. California and Washington were making boatloads of it. Now, no one cares, but the wines are still out there, and continue to show well in good vintages (see the 1991 Carneros above). Older Zinfandels can also bring similar value and charm.

This works at the high end as well. A Madeira from the early 1900s might set you back $800. But if you want something truly fascinating to open with a group of friends who aren’t wine nerds, a wine harvested before World War I is likely to be more captivating to a crowd than the most resplendent Grand Cru Burgundy from the 1990s. Likewise, consider vintage port—it may have a fusty reputation now, but that shouldn’t nullify generations of compelling tradition and world-class vineyards. Such wines provide opportunities to revel in the road less traveled. 

Let it Sit, Then Dump it Out 

Older wine will change with oxygen, and generally for the better. What at first seems like a shapeless mass will often come into focus after a few minutes in a decanter—clean acidity, toothsome tannins, and fresher flavors. Even if the wine turns out to be less than amazing, it’s miraculous how a bit of air can turn an old wine from off-putting to enjoyable.

Of course, that’s not always the case. If you rolled the dice on a producer you’ve never heard of, if the wine has the charm of stale coffee grounds in a forgotten percolator, your frog isn’t going to turn into a prince—which is fine because you played the odds and spent, what, 25 bucks? Dump it in the sink, open another bottle, and dump that one as well if it turns out to be similarly putrid. Find your way to something you like, knowing that all three bottles cost less than some random single-vineyard Cabernet sitting on the shelf at your nearest wine shop. 

Moderate your Expectations

Because so few of us regularly drink moderately priced wine that’s 20, 30, or even 40 years old, it can be a mind-bending exercise to decide whether such wines deliver a good value. The charms they offer—soft, rounded tannins in red wines; warm, autumnal flavors in whites—may also bring hints of things that a steady diet of young, modern wines has taught us not to like. Think a slight tang of volatile acidity, that balsamic note you often get in older reds. Or perhaps the earthy, green-pepper scents of pyrazines, which tended to be more common in red wines prior to the advent of modern viticultural techniques.

In the end, an old $30 wine bought at auction is a good value if it has a place at the dinner table as much as a similarly priced new release. If a dusty $30 bottle tastes like a wine that once had ambitions to taste like a $30 wine, that’s more than appropriate. If it’s pleasant but a bit tired, that’s also completely fair. Time, after all, doesn’t turn village-level vineyards into grand crus.

But I always give a few extra points for the “time capsule” effect, the way an older wine inevitably turns our attention to the past and to how weather and human decisions from decades ago continue to resonate. For me, a very good Merlot from Carneros evokes certain memories. In 1991, not long after Steve MacRostie harvested his grapes from Hudson Vineyard, while the wine was still bubbling away in the fermenter, my 10-year-old self fell asleep while trying to watch my home team, the Minnesota Twins, win game seven of the World Series. To me, that’s an experience worth bidding on, and one you can’t get at the shop around the corner.