There was a Tobacconist shop on Main Street for a long time, but I don't know if it's still there. On my last trip, they had a nice selection of cigars.
There is also a cigar shop at West End. Sosa Cigar Co. is the name. I've also seen a few at the deluxe resorts.
For Cigars I recommend "Cigarz" over at Citywalk. Certainly not fancy but a very good walk-in and a nice bar. Most of the WDW resorts have a small selection behind the counter at the on site stores but they tend to be a little stale.
Trying to be a little considerate I usually take a walk around the lakes or resort perimeter late at night or very early in the mornings. Just at sunrise walking around CS was my favorite time last trip no one around very quiet and they did not even have the constant background music playing.
UO seems to be more Cigar friendly then WDW.
RussH ...early Dec next trip.
Dreams Unlimited Travel is committed to providing you with the very best vacation planning experience possible. Our Vacation Planners are experts and will share their honest advice to help you have a magical vacation.