Well I can personally speak for the cigar part.
Corona Cigar Company
Coronacigar.com
Has three locations ...downtown Orlando one is largest and incredible. Full, and I mean full bar and great atmosphere.
The Sand Lake location is smaller but much easier to access during Orlando traffic (which is all day thanks to major construction and tourist ). Bar @Sand Lake can't compare to Downtown location but very nice none the less.
There are other cigar bars but they are "touristy" in selection and pricing. Cigarz at City Walk (Universal's retail/food/nightlife complex) and Sosa Cigars at Downtown Disney. Both convenient if your hitting those areas anyway.
My bet is Corona personally. Also Jeff the owner of Corona is very active in cigar advocate groups, Cigar Rights of America, fighting for our right to enjoy cigars so I feel good supporting his fine establishments.
Have a great time during your stay down here.