I’m not a fine of wine, but am curious, what is the better wine, that which somebody with an eye for wines can pick out of an off-license for a fiver, or that that would be available to senior nobles in England in 1300? I can see it likely either way: quality is quality and nothing will change that, or improvements to the process have mmade it so that the commoners wine has now surpassed the nobles wine of 800 years ago.
My money would go on modern-day plonk. Your 1300s wine wouldn’t be bottled with cork, so it would likely be either halfway to vinegar or fresh from the barrel. They aged some wines, of course. Even the Romans knew about vintages and the better vineyards. But I’ll still go with modern mass production. Heck, I’d put Gallo Hearty Burgundy up against anything the 1300s produced in semi-bulk.
There have always been lots of varieties of wine so I think it would depend on what wine the person liked. I for one would much rather sample an ancient Southern French or Burgundy or Beaujolais wine than a modern Bordeaux which most likely contains Cab which I hate. Even if it hasn’t been stored properly I’d still prefer the non-cab unless it’s literally turned into vinegar.
It might just be me but I haven’t had a really great sub-$10 bottle wine. I’d take my chances on the nobleman’s wine as well compared to that. But anything above $10 to me is a crapshoot, so even amongst varieties I like, some of the nobleman’s wine would be good and some would be bad compared to whatever decent-tasting non-complete-rotgut I was using as a benchmark.
I lived in China for two years and I found some great red wine for around $6(that is USD). I think the lower cost of living played a role. It was wine made and bottled in China, but it was fantastic.
China, and this was 10 yeas ago, had been very much trying to produce some world class wines, but having a terrible time getting any decent ones going. Has this changed over the last decade?
I found their average wines to be excellent. However, they had almost no expensive Chinese wines for sale at all.
And it depends on the type of wine, too. You can get some decent $5 wines today if you are looking at Pinot Gris or Sauv Blanc. A $5 Cab isn’t going to be quite as good on the 0-10 scale. But as the OP specified $5, I’m going to guess you can get a better wine in some places than your English noble in 1300 would be drinking. But not anything you buy today for $5.
I daresay the modern plonk has a lower chance of a fruity botulism aftertaste.
Cork has been used as a stopper since ancient times. Cork has been found in ancient Egyptian tombs. Cite.
See also here (pdf) though, they had yet to discover the tombs with cork. That pdf cites Horace saying that in Roman times the cork could be secured with pitch, though I wonder if the pitch was to protect from sea-water rather than to fix the cork bung in place.
That said, wine bottles weren’t introduced until the 1600s or later and wine in the 1300s was stored and transported in tuns. Read more here.
As for the wine itself? Quality control is much better these days, so a barrel of plonk now is going to be on average better than a barrel of plonk then. But a good wine? Assuming it’s not gone off (and someone will have tasted it before it gets to His Lordship, so an off wine will have been replaced), the quality will IMHO be much the same.
We had a very nice Cab last night that only cost $.05.
Of course, the other bottle of it cost $19.95. 
eta: Quartz, that’s why I said “bottled.”
Ah, Bevmo.
Here’s a little more information about alcoholic beverages of that era. Sounds like if you drinking his lordship’s wine you’d be doing all right.
Modern day cheap plonk, and it shouldn’t even be close. Our understanding of chemistry and biology, and the consistent winemaking processes they have fostered, is one giant reason. To pick on one process, adding Campden tablets is infinitely easier than trying to add sulfur dioxide to wine via a burning candle.
Consumer protection, either through regulation or much improved communications, is another big reason. All sorts of things used to be added to beverages, per Marvin’s link above, to hide spoilage, improve taste, and improve stability. Many of those, like solutions of lead to sweeten the wine, could be very bad for you. In the realm of Beer, the Bavarians didn’t come up with the Reinheitsgebot for the hell of it.
While tasting great wine, from say, Schloss Johannisberg, on its original rootstock, and cropped down to make wine just for you, would probably have been an amazing experience (Even though they weren’t harvesting botryzized grapes intentionally then.), the quality could not have been as consistent or technically clean as Two Buck Chuck.
The only possible caveat with the “modern plonk would be way better” argument is that the really cheap modern stuff is cheap for a reason – either it’s been mass-produced with the lowest possible cost in mind or it’s a failed vintage or failed production batch with significant flaws. It may well be that much or all of this would still be significantly better than 14th century wine, but I think the more interesting definitive answer is that if you move up to even a moderately priced contemporary wine, there’s no doubt that it would be far better than anything available in those days, and that’s really the moral of the story.
I’m tossing a small vote in for “Modern Plonk” (bandname?) but is it cheating to mention fortified wines and the like? Those, ostensibly, would have avoided some of the storage issues, and some of them have had the same or similar recipes since the Pope was of uncertain gender. Commandaria is basically an aperitif wine (think vermouth) and has been made in the same mode for over 2000 years. In the middle ages, a lot of monasteries made, nay, specialized, in similar products–herbalized, stronger wines that lasted longer and were more consistent–leading to such beauties as Chartreuse and Strega and the like. And part of the reason was to minimize corkage yuck and other storage difficulties.
So, the strictness of your definition of “wine” will delineate your question. From my research, I’m going to guess that table wine (your equivalent of modern-day Barefoot wine or whatever, except it was probably made by a guy with whom you were on a first-name basis) was more iff and unreliable, if not altogether worse, but it would be made up for by the nice tun of Jerez that just came off the ship, or the Benedictine you’d sip after supper. If, of course, you were in funds that year.
(This is a bit of a hobby of mine.)
Either would be perfectly acceptable offered to an alcoholic.
How can you possibly know?
General anything-tightedness. Pitch-proofed cork was also used for oil, jams, fish preserves… anything you can store in a clay jar.
I’ve had ale, cider, and mead brewed using medieval techniques and recipes, and it’s all quite good (though the ale, in particular, is very different from the modern version and is a bit weird to a modern palate). I expect medieval wine would also be good, although again, pretty different from what we’re accustomed to.
But… but… but… the old way is ALWAYS better, isn’t it?
Whatever this non sequitur means. No one can know because we have no way of knowing what the older wine tastes like. And, modern food and beverage have traded flavor for size and durability. The chicken offered at a stand in a Mexican village is smaller but far tastier.
I think most modern palates would find the kind of wine that 14th C English nobles would have enjoyed probably too sweet (that’s projecting from the medieval love of hippocras & piment, and the later English devotion to sack, malmsey, port and madeira).