Personally I don’t think I’ve ever tried anything over $30. 
Chateau Latour 1975. It was more than $20 
What’s the most expensive wine/spirit you’ve ever tasted or bought?
With or without the little straw basket?
I’ve got a bottle of Scotch that I bought on sale for $80 about 10 years ago. If I were to replace it now, it’d be about $140.
“Servants! Bring me a carton of your finest wine!” – Franzia the Great
I’ve been plied before with old Remy Martin cognac that I’m confident was over $250 a bottle, but that’s at the hands of rich relations, and one time only. The most expensive spirit I’ve ever purchased myself is probably some Glenmorangie at about $45 a bottle.
Took a wine class about 10 years ago, at which we tasted a $150 bottle of an outstanding Bordeaux, though I can’t remember now which chateau or even which appelation. I do remember that it tasted as if it were worth every bit.
At a memorable visit five years ago to the Napa Valley, my wife and I dined at Domaine Chandon. It was in early February and the place was nearly vacant. We had superb service, excellent food, and a $60 bottle of the host’s champagne to match.
My wife one spent about $75 on an 18-year-old single-malt Scotch for me for a birthday present.
A Chateau Margaux which I purchased, in Bordeaux, in 1998, and I finally popped it open and enjoyed it last year with some fine local elk. (On the plate, not as dinner guests!)
I can’t recall, but I think it must have set me back maybe $50 or $60 at the time.
Several years ago, the wife and I ended our New Year’s Eve eve eve dinner at Olive’s (Bellagio, Las Vegas) with their “Flight of Cognac.” The last snifter contained an XO that I later looked up. $400/bottle. It was superb.
Several years ago, I had a glass of madeira from the 1860s. I don’t actually recall how much it cost, but it was quite a bit.
At home, I have a bottle of tokaji esszencia that I picked up a few years ago; at current prices it would probably go for a bit over $400. I also have a couple bottles of port that would go for somewhere over $300.
For non-vintage stuff, I generally keep a couple bottles of Chartreuse VEP (green and yellow) on hand; they go for about $120/bottle.
I’ve had the Chateau Latour 75 too, it was very nice. But my most expensive was a glass of Louis XIII Remy Martin Cognac when I was feeling particularly flush. $115 a glass (about $1500 a bottle). It was very good and the best Cognac I’ve ever had, but not worth it to me to repeat. The best wine I’ve ever had was a 1982 Beaulieu Vineyards Georges Latour, which I found at Lucky mispriced at $15 for the bottle back in the early 90s. It was to die for.
I bought a bottle of Dom Perignon back in the 80s for about $80, having tried a glass or two the previous summer. It was a special occasion.
Lately, I’ve treated myself to some semi-expensive beers ($50/half-case for 32 oz. Sierra Nevada or $10/sixpack for Dogfish). I paid twelve bucks for a glass of stout I didn’t particularly like, so I apply my purchasing power a bit more carefully now.
I’ve had plenty of Champagne in the $200-$250/bottle range (retail, not restaurant prices). Is it worth it? Well, you can tell the difference between a cheaper bottle, but there’s so much good stuff out there in the $50 range, overall, I’d rather have 5 $50 bottles than one $250 bottle.
I’ve also had some damn good wine when I worked in a wine store. I can’t say what the best was - but I know I had some very pricey bottles there.
I had wine in Italy that I was told was in the $200-300 range over here, unfortunately I don’t have a taste for wine; it was good but didn’t strike me as being all that special. I’ve had Scotch at whisky tastings however that really blew me away, mostly in the $80 range; there’s a $1000 bottle of Glenfiddich at the liquor store right now that I’d love to try, anyone want to split a bottle?
I bought a bottle of Dom Perignon back in 1999, for over $100. It was for New Year’s Eve. Eight adults, and we all got one glass to toast the New Year. It was delicious, but a one time extravagance.
Yes, I know it wasn’t the millennium or even the century, but dang it, that’s when folks were PARTYING!!!
Maybe ten years ago, I bought the husband a bottle of 30-year old Bowmore scotch for Valentines Day. It cost about $250. I made a joke at the time that the scotch was only a year or so younger than me. Anyway, the aroma of the scotch was so strong you could smell it all the way across the room. We still have the bottle which has a dragon on the label.
My brother-in-law got a $1000 bottle of cognac for Christmas one year. He asked if I wanted to try some and I was like “hells yeah.” It was very good, but I couldn’t taste the $980 difference between that and Courvoisier.
I’ve tried Blue Label, Chivas Royal Solute, and Pierre Ferrand Abel. I think they all cost around $200, though I’m not sure.
The best way to taste expensive stuff is to sign up for tasting classes. Most of the people there are light weights and you’ll get more than your share of good alcohol that everyone paid for.
Once you get to liquor that is worth more than $150 it has almost no flavor. Blue Label tasted like nothing. Some people prefer Gold Label because it has a lot more flavor.
The most expensive wine I’ve ever had was Castello Banfi Rosso di Montalcino for $20. Well worth the price.
I tried a 30 year-old cognac that I think was about $500/bottle. It wasn’t that great, but it was older than me, so I guess that’s something.
I had some Mumm’s champaign-about $120/bottle-nothing special. I also had some Ballentine’s 30 Year Old cotch-very nice (about $150/bottle).
We were at some artsy-fartsy thingie many years ago and the High End Nobs plied the crowd with some Rothschild wine ( I think it was Rothchild, I drank ALOT of it and ended up insulting some guy’s taste in tie-wear.) .
I’ve stuck to wine-in-a-box since then.