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Here's where it gets tricky: in an effort to help you discern the quality of the wine in the bottle (beyond the price) they have hierarchal terms that appear under the Chateau's name on the label. I will attempt to explain:
  • Bordeaux: the lowest level, grapes can come from anywhere in the region, basically cheap, everyday table wine.

  • Supérieur: Still table wine, but of a better quality, stricter rules about winemaking, growing, etc.

  • Cru Bourgeois: A new law in 2003 re-classified 247 Chateaux that were not previously ranked because they showed great quality despite being outside the original classification system. A number of them are considered to be better wines than some of the lower Grand Cru Classés and their prices reflect that distinction.

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  • Grand Cru Classé: Chateaux that were classified in 1855 and ranked according to quality and price (First-Fifth Growths). There has been only one change since then, so though they still technically rank the highest in quality, they don't exactly have to prove it. There are only (5) First Growths: Ch. Lafite, Ch. Margaux, Ch. Latour, Ch. Haut-Brian and Ch. Mouton-Rothschild. These wines are known throughout the world and are highly sought after. Their quality and scarcity is reflected in the price.
Wines from the Medoc and Haut-Medoc, which includes the following communes – Saint-Estephe, Paulliac, Saint-Julien and Margaux – as well as Pessac-Leognan and Graves are mostly CABERNET SAUVIGNON based.

Wines from Pomeral and Saint Emilion are all MERLOT based, along with most of the wines labelled merely Bordeaux, Bordeaux Superior or a Vin du Pays from Bourg, Blaye or Fronsac.

All this being said, you could spend decades trying to figure out the best wines from this region. Thankfully there are plenty of people already doing the work for you. VINTAGE ABSOLUTELY MATTERS. This is a cool growing region and the weather plays a huge role every year with vastly different results. These are also wines that need to age to come into their full form. The higher the price, the longer you should wait.

The best overall recent years: 1989, 1990, 1995, 1999, 2000 (except for Sauternes), 2001 (for Sauternes), 2005.

The best way to get Bordeaux is by buying FUTURES. This practice allows you to purchase the wines in advance of their release (you usually have to wait 3-4 years for delivery) at a dramatically reduced price. They still aren't cheap by any means, just more affordable, plus you don't have to store them at your house while you're waiting for them to mature. All the major wines are taste-tested and rated, so all you have to do is read the reviews and pick out the ones that suit your taste. It is a bit of a crap shoot, but wines rated well in good vintages are going to be worth the money.

HOWEVER, before you go dropping a lot of cash on these wines, I suggest tasting a few of the cheaper varieties like the Grand Crus' second labels or a few Bordeaux Superior, especially if you're only familiar with New World versions of Cabernet/Merlot blends. Bordeaux have a distinct flavor profile you may or may not like and you can't return them once purchased.

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