Being a guy that has had the luxury of smoking some incredible cigars over the years this is really hard... but here are a few of my personal, most memorables:
Habana Davidoff Dom Perignon - 1987
Habana Dunhill Don Candido - 1965???
Habana Bolivar Gold Medal - 1983/84
Habana Quai d' Orsay Imperiales - 1994
Habana Trinidad - 7 x 38 - Diplomatic - Pre-Release - 1997
We have been working on trying to recreate a really epicurean smoke for about two plus years now that would fit into this esteemed class of uber-elegant smokes under the code name "Tranquillo", but I will admit it is very difficult to make a new cigar that gives you the smoking experience of a two decade old, properly aged cigar. We are getting closer, but I have my doubts we will be able to blend something new that will ever compare to something truly vintage. Only time alone can create certain nuances imo.
BR,
Steve Saka
President, Drew Estate