I was there over winter break, wish I lived in the area to go meet up again. The whole main drag there where the restaurants and clubs are is filled with cigar girls walking around trying to sell cigars so you shouldn't have a hard time finding a place to smoke. A lot of the dining establishments have outside tables (but the food there is NOT cheap)
You can also check out Versace's house while in that area.
You can also check out 8th street AKA Calle Ocho AKA Little Havana for some great food and probably some good places to sit outside and smoke while having a café cubano (cuban coffee) and/or sandwhich