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I find it very hard to choose my whiskys. I can buy Glenlivet 18 for $86 CDN where I live and love it. The problem I have is most 12 -15 yo in my area are same price or only few dollars cheaper and other 18 are considerably more expensive like $30 plus. So how do i convince myself to buy a 12 that's only slightly cheaper than the livet 18? silly I guess.
I guess you are located in Canada where alcohol taxes are high. Living in Norway, I am quite familiar with that problem. There are some things you should consider:
1. Older whisky is not necessarily better. Sure, with high tax on liquor, it is tempting to go only for high age statement, as it's only slightly more expensive than 'standard bottlings'. Glenlivet 18 is a decent malt but there is so much more to discover. Try some different stuff, with and without peat, with and without sherry cask influence.
2. Look out for miniatures (5 cl) and 20 cl bottles. These are a great opportunity to try a wide range of malts and find out what suites your palate! Check online retailers and see what you can find. Diageo's 'Classic Malts' might be an option for you.
3. See if there is a whisky club in the area you live. Especially when alcohol is expensive, it is good to share the costs and test different stuff.
Hope this helps.
“That's what I do. I drink, and I know things.” (Tyrion Lannister)
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Go with the whisky that you like and fancy and buy and enjoy that one.
Whisky does not live from the age alone. The selection of casks (Sherry, Port, Wine) is as important as the amount of smoke, the duration of the fermentation a.s.o.
Have a look at the smoky whiskies from Islay. They are a lot more expensive than the ones from the mainland. Whiskies like the Ardbeg Uigeadail or Laphroaig Triple Wood carry no age statement at all and they have the same (high) price. They would not be on offer, if people weren't buying them. And whisky connoisseurs are knowledgeable people.