Theres a great B&M on Newbury St & Gloucester St, called Gloucester Cigar Company. It's owned by a short fat guy named Jose. He is a cool guy, smokes at least 15 cigars a day. Goes through them like cigarettes, I swear. I have sat there smoking a cigar, and he smokes 3 in the time it takes me to get through one.
There is a cigar lounge that serves wine and beer right next to Faneuil hall called Churchills. Joe should be the bartender there, great guy. The place also has a walk in humidor with an okay selection (it's not great, but the atmosphere is. Leather seats, dim lighting, a great view of Quincy Market).
A cigar place in the North End, called North End Cigars, right on the main street there (Hanover St, I believe it is). This place is expensive, and I would recommend walking to Churchills rather than buying there, since they are about a 10 minute walk from each other. But if you want to smoke a stogie while chomping down on a Canoli from Mike's pastries, by all means.
If you are looking for something quick and don't have the time to make it downtown (I don't know where you will be staying, but this is the one thats closest to my campus), there is a store in Kenmore Square (right by Fenway) that sells a VERY limited number of cigars called Sugar Daddy's. They card at the door, and the place is kind of shady. It is mainly a water pipe/hand blown glass pipe store, but they sell shisha and other pipe tobaccos there. I would only go there as your last resort. You're likely to get addicted to crack if you step inside
.
There is also a smoke shop (not just cigars) on Newbury street called Kang's Smoke Shop. I haven't been there personally, so I don't know what kind of cigars they sell. If you are there alreay though, you might as well make it to Glocuester and pick up some sticks there, they are only 1-2 blocks away from each other.
I am sure there are more, but I don't know of any off the top of my head (I have only been living there 9 months.)
Out of all these, I recommend Gloucester street for the selection and the price, and Churchills for the for the atmosphere. If you are over 21, a nice pint of Murphy's will go well with any smoke, and you can get that at Churchills only.
Keep in mind that Boston does have an indoor smoking ban for all businesses. The only exception is if the business makes 75% (I am not sure about this figure, it might be higher) of its profits from tobacco sales. Because of that, you will not find a full bar and a full cigar bar anywhere. Churchills limits its selection to wine (I think it's even more limited to just ports, not sure though) and a selection of 4-5 beers. (I know Murphys, Sam Adams and Bud are 3 of them).
Hope this helps.
I would join you for a herf, but I am in CO for the summer
