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It's like buying real estate...except opposite.
Savvy wine buying is, in some ways, the opposite of real estate: with real property you want the worst house on the best street, but if you dip your toe into the lowest-price wine in a pricey area like Bordeaux, prepare to be disappointed. Instead, the key is to find an area with great fundamentals—old vines, a long history of winemaking—that hasn’t been discovered yet, and then go to the top of the market for their best bottles. In Burgundy this strategy might cost you $5,000 a bottle, but on the southern coast of Sicily you can spend $40 and be a baller. Case in point: the $38 Feudo Maccari Saia 2013, a wine made of the often humble Nero d’Avola grape, which delivers a wallop of red and black fruits, some mint and some savoury notes in an opulent package that will see you through the coldest fall day.