What drinks or food do you choose? I can’t tell what is my priority. But I like Latakia and Island Whiskey. Virginia is good with tea or Dr. Pepper.
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I find that sweeter blends like Virginias don’t pair all that well with beer - a sweeter beverage (for me, diet ginger ales) or a whiskey work well with that.
Beer seems to work pretty well with more in-your-face English blends.
Take all of this with a grain of salt, though - I have been a cigar smoker for decades, but I didn’t smoke a pipe for > 10 years until a few weeks ago. :-)
I’m thinking that a lot of my cigar pairing will work well with a pipe, though.