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.
Root beer is surprisingly good with a lot of burley blends.
So far I haven’t found any tobacco that doesn’t go with tea. It’s such a good combo. I really like it with Chelsea Morning
I agree with tea. With all the variety of different types of tea and the same number of tobaccos, finding a combination that will create a wow effect can be difficult. But tea is a safe bet.
I haven’t really delved into trying to varieties with each other, just smoke and drink what I would normally have. Oolong and aged white teas are my main go to
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.