OT: Going Han Solo on some Cuban Cigars

I honestly thought it would be a jhackney post.

Umm....  Common myth:  Cigars are not better just because they're cubans.  In fact, the price on cubans is inflated because there are so many people who have this perception that they'll pay the higher price thinking "Oh! It's Cuban!" and automatically thinking it's somehow better.

These people are n00bz.  

If you *really* want a cuban, get a good one like a Cohiba (make sure it's a cuban Cohiba not the other kind)

If you don't wnat to shell out for a good one, then save your money.  For the price of a "cheap" cuban you could get a very good cigar from DR or elsewhere which will be just as good if not better than a cheap cuban.  A Fuente Opus X will be way better than a cheap Cuban.  So will an aurora Cien Anos or a Graycliffe. 

(Diclaimer: It's been awhile since I smoked cigars but I used to smoke a cigar 2-3 times per month).

Are we  talking about people

I heard all kinds of horror stories about customs, but when I came back from italy with some the agent didn't even check...

In your butt.

Be careful who you're smuggling for. Although the Hutts have the most money, it's just not worth the risk anymore.

What maizenbluedevil said about the quality is completely true.  Primarily due to the trade embargo with the United States the cigar industry in Cuba is not what it once was.  That being said if you go with quality like a Cuban Cohiba you will not be disappointed.  They were what I was going to recommend prior to reading everyone elses comments.  Now for the tricky part with customs.  The last time I was in South America was 2005 so my experience might be a little dated but when entering the United States the biggest concern with bringing in cigars is if they are banded or not.  If you don't want a hastle from customs ensure you take all the bands off the cigars prior to packaging them for travel.  When packaging for travel if you don't already have a travel humidor and are not otherwise in the market for one don't waste your money.  You can have an equal amount of success with a ziploc freezer bag.  The temperature difference you will experience while traveling will not be for a long enough time to make it matter and as long as you drop in an adequate amount of either humidification sticks or pillows which you should be able to purchase anywhere you purchase cigars you will be fine.  I hope this helps and if anybody has more current customs information than me please speak up.

I'd rather go Bill Clinton with my cigars, but that's just me. 

You should be fine just keeping them in your carry-on, I've done it several times without issue. As someone said above, get a travel humidor. If you're bringing a whole box back, I'd pack them in something else and remove the bands. 

Remove anything that identifies them as Cuban - ditch the box and the bands. At that point there is nothing to distinguish a Cuban from any other cigar. Also, agree with several others - they are not good just because they are Cuban, many of the finest smokes out there are from elsewhere. However, a legit quality Cuban (such as the real deal Cohibas noted above) can be very tasty, although also expensive.

You might want to check a cigar website to verify legit bands/boxes from counterfeits.

Have you ever seen the tv show "Locked Up Abroad"? Netflix it.

If the price of the cigar seems too good to be true, it (of course) is. It's not at all un-common for people/stores to put fake bands on cigars and Cuban in order to prey on American tourists. If you do decide to buy them find a reputable business to purchase them from, avoid anything too touristy. If you're not willing to pay a decent amount, there's no reason to get Cubans because you'll just be paying a premium for the country of origin.

Now, if you're looking to get some Cubans just for the novelty of it, go for it. If you're expecting them to be miles ahead of what you can get in the US, don't waste your time. Yeah, a good Cuban Cohiba or Montecristo will probably be great, but it's going to cost the same or (more likely) more than an equally good, if not better cigar from Nicaragua or the Dominican Republic.

As to sneaking them back into the US I have no suggestions. I know people who have had no problems at all, and I know people who have had them confiscated, more often than not people seemt to bring them back without too much trouble. Putting them in a checked bag seems to be the easiest way. However, you should know that maintaining good humidity and temperature is crucial to keeping the cigars in good quality (70 farenheit at 70% humidity is a good rule of thumb) and maintaining this in the cargo hold of an airplane is quite difficult. 

My advice? Buy a good Montecristo or Cohiba in Brazil and smoke them with a great cup of coffee. Then come back to the US and buy an Opus X or a good Padron (like the 1964 or 80th anniversario). Even better, find your local tobacconist and talk to him about what's good that he has in stock. [Time for a shameless plug->] If you're in Ann Arbor, come to Maison-Edwards and we'll get you situated.