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  1. For Riga... Definitely Riga Central Market, as mentioned above. At least to me, Latvian rye bread is a real delight (very dark and dense) (there was a recent piece in Saveur about regional differences in European rye breads). Look for piragi, the delicious Latvian ham rolls. I'm blanking on the name of my favorite place and my trip notes are elsewhere, but based on the location I think it ay be the place referenced in some other posts, Rausu Meistars located on Gertrudes Iela. You'll also find some at the Central Market. Riga Black Balsams is a treat if you like bitter, amaro-style liqueurs, only just beginning to become available in a few places in the US. (In Estonia, you'll find the sweetish, vanilla-y liqueur Vana Tallinn, also a treat that I believe is imported nowhere in the US.) Sadly, as my notes are elsewhere, I can't remember other restaurant recommendations, but there was a NYTimes 36 hours in Riga piece a few years back that might be a good starting place.
  2. Yes and no. The best way to learn about aging wine is to try it -- buy a half-case or case of some wines (can be inexpensive while you're learning about it) and open one periodically, watching as and how it evolves. As you notice what changes, you'll start to figure out what to look for when the wine is first released. And seek out opportunities to taste verticals of wine -- newer and older vintages of the same wine, which can give you some clues (of course, some years produce longer-aging structures of the same wines than others). But keep in mind that even the most experienced critics' and winemakers' predicted drinking windows can be (often are) way, way off, in both directions. It's all guesswork, some more educated than others, and complicated further by the fact that tastes vary widely (just because a wine can age doesn't mean you'll like the aged version more - another reason to experiment on your own). And, increasingly, wines are being made to be drunk younger to satisfy those who lack the time/patience/money/etc to age wines. In general, 'balance' would be a key criteria for age worthiness, though that's obviously a slippery concept. Tannins (especially for red wines) and acidity have a lot to do with a wine's ability to age, and balance often has to do with the interplay between those. People suggesting drinking windows are usually combining some general knowledge of how that wine has done in the past (e.g., is it a varietal that ages well, does that particular bottling have a history of aging) with an assessment of the particular bottling's balance, ripeness and fruit sufficient to hold up to aging, and enough tannin and acidity to give the wine structure in years to come. And a fair amount of guessing and luck... Hope that helps a bit. Jancis Robinson's books are a good place to start if you want to read more about aging wine (her Oxford Companion to wine has some entries on aging that talk a bit about the science behind it as well).
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