Legally buy them(in Nassau)? yes. Smoke the heck out of them in port and at sea. yes. Bring them into the US. No. Likely to get caught, no. Embarrassed to call home and ask parents for money to pay huge fine if you are not lucky? yes.
My advice, leave the Cuban cigars alone. Let your neighbor buy his own. Bring him a tacky tee shirt.
Well I guess I'm a smuggler because I always bring Cubans back with me. I just take the bands off them and walk right through customs with no problem. They can't tell where the tobacco was grown. However, when purchasing Cuban cigars you have to be careful because there are some fakes being sold in Nassau (and other areas I presume) and they are not as cheap as you might expect. A decent 6" cigar will cost about $12 - $18 each.
No... the trick is to know that any purchase in excess... including jewelry... will be noted and can be passed on by the very people from whom you've made the purchase. If you're planning to buy that gold Rolex for 12 grand, or whatever, better give some thought to declaring it. Buying some Cubans?... just take a few.
Apparently there's a smuggler psyche for both cigar smokers and wearers of fine watches. Be aware, however, that Bahamian shops have been known to contact U S Customs with the names of Rolex, etc. purchasers and which ship they're on. Informants can earn up to 25% of any penalties paid by the offending smugglers. And you can take that to the bank!
Tsk tsk! Do you really think that our government would do something illegal? Before you contact the media about this, you should be made aware of Section 619 of the Tariff Act of 1930 (19 USC 1619), entitled "Award of Compensation to Informers". This law provides for compensation of 25% "...of the net amount recovered, but not to exceed $250,000 in any case ...." for anyone who reports violations under the customs or navigation laws to an officer of the customs. That law's been on the books for over 70 years, and many crafty "informers" have taken advantage of it many times (including Bahamian shopkeepers). Just thought you'd want to know.