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re: Chicago Mike
Muscat de Beaume de Venise is another good recommendation, though I would be careful about *which* one I would choose. Personally, I would want something with a bit more weight than, for example, Domaine Durban -- probably something like Domaine des Bernardins . . . or maybe even a Muscat de Riversaltes instead.
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Since chocolate cake usually delivers a less intense chocolate experience than other dessert, you have a little more leeway than you would with, say, chocolate mousse. If you want to go the port route, a tawny would be your best bet. Banuyls, Maury or Riversaltes, especially older, slightly oxidized wines (analogous to tawnies), would also work; in fact, they'd be my first choice.
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It might not be to your taste...but how about a Sherry with chocolate?
I agree that ports and chocolate don't necesarily go together, although if I were to pick one port, it would be a Reserve blend (ie. Dow's 'Christmas Port' Reserve this last winter was a fantastic pairing with chocolate!).
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re: zin1953
I am basically with you on this one. The reason that I had mentioned the LBV (should have specified "new-style" over some of the traditionals), is that the astringincy, that I find in many LBV's is likely to cut through the fat in the chocolate. Still, Port is NOT my first choice. If it were my menu, I'd drizzle some raspberry compote around and do an older US Merlot. I still have a half-case of the Beringers Howell Mtn. Bancroft Ranch '89 (yeah, that horrible '89 vintage from Napa), that is still holding up wonderfully and loves both raspberry AND chocolate - just not too much "milk."
I need to refresh my palate on Banyuls. I've got a smathering of mixed producers and vintages in the cellar, but hardly ever reach for it. I'll do some comparisons, and see what I'm missing.
Thanks,
Hunt
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First choice would be an LBV in your price range. I'm, personally, not a fan of having Vintage Port with food, except for some cheese and nuts, after dessert. With food, I'll usually grab a Tawny, but with the chocolate, I can't quite get my palate around that profile with any Tawny, that I know.
Another option might be to do a domestic (US) Zin port-style wine with the chocolate, or some Young's Double Chocolate ale - but you did ask for a Port.
Hunt

