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Recommendations

PLPCs are my favorite cigar. They're relatively inexpensive, and they age very well. Even in bad production years, they are still pretty good. The flavor is medium, so not a bad first cigar for your son, but enough flavor to keep connoisseurs interested. And they come 50 to a box, so you could have 25 dates with your son.
 
My boring answer is that a cigar like a RASS really benefits from 8 years of aging. Too bad they're around $30 a stick these days.

Seconding Padrón 2000 as well.

Edit: Also agree with Nihon_Ni
 
Alright, just spitballing. Buy a couple of your favorite sticks on his birthday for each of the next 8 years. That will allow for palate changes and give you both 8 different cigars to choose from on his 21st. If he's into the experience that will give you several opportunities to talk about the year you bought that individual stick, what was happening that year for each of you and your family and ultimately how our taste in pretty much everything changes over time or just get one of those "cubans" and forget about the cigars.
This is a neat idea, makes for a nice collection to pick from and the opportunity to share a special stick more than once.

Okay, I gotta bite, A few of you guys are recommending Cubans. Aside from a trip overseas (Portugal may be in the not too distant future) how in the world do you get them in the states???
 
Once upon a time, smokes from the forbidden island could be mail ordered over the internet at often very reasonable prices. Lots of reputable vendors. Lots of folks did just that. Then...the prices went to the moon. Smokes you could get for $275 suddenly shot up to $1200+. Went from a wonderful splurge to financially prohibitive for most folks. Also, several vendors quit shipping to the US as tariffs and such made it extra sketchy. Lastly, there was always the risk of confiscation by customs though that was hit and miss. At least that's what folks tell me.....:rolleyes:
 
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