An insight that really improved my cooking over the past few years: if you buy 1gal bottles, you can get super-fancy olive oils and vinegars for the same $/oz as a typical supermarket bottle. (Store in dark, cool place, transfer to small squeeze bottles!)
Conversation
which olive oils and vinegars do you recommend?
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Olive oil: Seka Hills[1] is outstanding and can be had for $0.60/oz in bulk (about $20/mo for us). I really love Wonder Valley[2] too but alas even in bulk it is $2.38/oz.
[1] amazon.com/Seka-Hills-Pre
[2]
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Vinegar: Katz's[1] for white, red, and sparkling wine vinegar (~$0.65/oz, about $10/mo each); Napa Valley Naturals for white balsamic and cheap balsamic for cooking (I get from Rainbow here in SF, having trouble finding online).
[1] store.katzfarm.com/artisan-vinega
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True balsamic vinegar and sherry vinegar can't be bought in bulk. I buy the former in Italy while I'm there (~$90/100mL; Cavedoni is amazing); the latter from specialty grocers (Motegrato Pedro Ximenez is great).
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Oh, looks like the Cavedoni DOP balsamico is actually available online, and not really marked up. Nice! casadecase.com/cavedoni-ducal

