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At some point I got very sick smoking one while drunk and since then they have kind of disgusted me, but for 3-4 years I really liked them.
The Cohiba Esplendido is kind of a standard. Very fine cigar. Nice but not overpowering flavor, burns perfectly and that is because they are meticulously prepared. Flavor is outstanding, sort of sweet n salty with robust tobacco aroma and flavor as well. The Robusto and Exquisito are along the same lines. I would probably get an Exquisito because it's not so goddamn big.
If you like something earthier, try Bolivar. The Royal Corona is splendid and I have heard good things about the Belicoso Fino. Personally I don't care for that sort of flavor but I can appreciate it just the same.
I once tried a Viliger cigar, I do not remember what it was called. It was sort of an afterthought to the guy who had the business, but I thought it was pretty good. Very fine smoke, slow-burning and kind of chocalatey. I do not know if it is made any more TBH. This was called La Flor de something or other, had a blue label. Frankly I don't remember where it was from, I guess I just assumed it was Cuban.
Now, you may be frustrated as so far I have named Cubans and you may not have access to them as I did living abroad. Fear not as two non-Cuban choices may be the finest, and they are both found in the $15-$20 range to boot.
For Dominican cigars, Arturo Fuente (and now his heirs Carlos and Carlos Jr) have often turned out a special product. I have had a couple from their stash and they are really nice, even though they are a bit spicier/sharper than I generally like. I don't remember what the one I had was called, came in a brown leather case, but a year or two ago they won several awards for one called Ojo del Tiburon or eye of the shark.
Now, I saved the best (IMHO) for last. Padrón. Nicaragua. This is a robust smoke, flavor like I never felt before, almost too strong but the subtle notes to it temper it and enhance it all at once. The smoke was unusually thick and almost kind of silky, very fun to play around with. I had a couple puffs from different ones but the only one I smoked whole was from the 1926 series. This was a special cigar. It made the Cohibas I smoked--which were many, not just the Esplendido--feel like a stale Black N Mild from the corner store.
And you will know MY JACKET IS GOLD when I lay my vengeance upon thee.
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