The local crowd is very hospital and friendly. They invited me to the Tuesday night pairing, which was a very interesting experience for me being a new cigar smoker will definitely mark it and be back. The owner is very knowledgeable about his cigars. read more

This is my experience and my review. I had been a loyal customer of Chesapeake Pipe & Cigar for quite some time and regularly spent significant money there because I genuinely appreciated the shop, its products, and what I believed was a valued customer relationship. When I was previously told that "everything is for sale," I took that at face value. I made a special trip specifically to purchase Pembroke, only to be told I could buy just two tins. That experience left me feeling disappointed, disrespected, and honestly hurt. I had thought I was considered a good customer and that the relationship I had built with the shop meant something. I fully understand a business can set limits on rare products. What was difficult was the inconsistency between what had been communicated to me and what happened when I arrived. For me, it was not just about tobacco--it was about feeling undervalued as a loyal customer. Because of that experience, I no longer feel comfortable doing business there and will be shopping elsewhere going forward. ...and giving excuses or having pride for actions, issues, or problems is what the establishment does, if you don't like it go elsewhere. read more

I can't tell you how absolutely disgusted my partner and I were with the quality of the cigars at the Chesapeake cigar shop. We went with high expectations but hated every cigar we sampled. Cigars were stale and made with inferior tobacco. We were embarrassed that we spent a lot of money on such a poor product. Everything we tried was just awful, however they had the nicest guillotine cutter. The cigar cutter was just amazing. We both agreed to never come back, unless we wanted a tacky decor w cheesy quips and slogans abound. Please save you money, too many other quality cigar shops around. read more

We visited this shop on the DC Cigar Tweetup. At first I was really turned off with this place. A big sign at the front reads "If you didn't buy it here, you can't smoke it here." Isn't it just normal to charge a cut fee? Isn't there a more tactful way to say this? Inside, the humidor was a decent size and the front area has some nice seating. In the back there are double doors (which I assume they must close sometimes?) and more couches and tables including a dominoes table. Cold drinks are available here to purchase. There are large TVs everywhere. The owner was really friendly and great to talk to. Very helpful and personable and changed my view of the shop. She's got a great reason behind doing what she does - a nurse helping wounded veterans. The worst part of this shop was the members. Poor etiquette, bad hygiene, and unwelcoming to others. One told me flat out that we weren't welcome there. Very sad to have people like that represent your business. I really wanted to give this shop a better rating after meeting her. But it just wasn't enough. It was unwelcoming in the front, and unpleasant in the back. Edit: I improved the rating of this shop after some months since being there because it wasn't the shop's fault that their member was very rude. read more

Chesapeake Pipe & Cigar - Tobacco Shops Near Me - Annapolis, Maryland

Hidden secret in Annapolis. Traditionally in Annapolis it was a pipe town and this shop keeps that tradition alive. They also have a great supply of cigars and the owner/operator is very knowledgeable and helpful. Voted best of Annapolis multiple times now for best place to smoke. read more

Yelp, Google and even the voicemail greeting state the shop opens at 11am on Sunday's. I arrive at 11:40 to the dark, unopened shop. Sign on door says 12pm. Ok, no problem, I'll wait. Come 12:10, shop still unopened, not an employee in sight . I've only wasted 30 minutes of my morning waiting for someone to open the shop. But again, no problem. Went 10 minutes down the road to MoJo Cigars, was treated like royalty and ultimately got what I needed today... a freakin cigar! Funny how business works; gotta be open to sell your product. read more

Owners nice some known good cigars at prices that are a little high. Friendly atmosphere however the 4 or 5 times I've been in here there is always a guy on the couch talking loudly on the phone, seems to use it as his office. read more

I only frequented Chesapeake Cigar company a few times when I lived in Annapolis, and I found myself quite fond of the shop. They definitely have their "clique" group of locals, like any tobacco shop. Mike seemed like a nice guy and he has a terrific lounge with ample room. The cigar selection was great... the prices were a little higher than the competition in the area. I would definitely stop in again if I am ever in the area. Very good overall tobacco shop. read more

My favorite cigar shop in the area! The only thing that keeps me away is their prices are so high! Good selection of quality smokes. Friendly and helpful staff. Great lounge area to kick back and relax. read more

I love this cigar shop! Mike is an extremely friendly business man. Stop in for amazing cigar deals and a great atmosphere to smoke in.

Nice place to enjoy a good cigar and a ball game. My buddy and I stopped in for a couple of cigars and a drink (BYOB) last night. The owner Mike is a friendly sort with an eye toward customer service. The humidor has an excellent selection of cigars ranging from the moderately priced to the luxury bands. The prices are what I expect from a retail front that provides the kind of lounge and amenities found here. I will stop by again! read more

Stopped in a few times over the years when commuting from DC through Edgewater, While the lounge in the rear of the store is the biggest & the best in the area, one does at times feel like an intruder in this shop. The humidor is large but lacks popular brands and the prices are high. For some reason there are numerous empty/open cigar boxes on display, perhaps to create an appearance of being well-stocked? Not giving up on this place yet because of their lounge, just wish he had a better selection (and price range). read more

Ok so I do not smoke cigars but my little brother does. When he comes home (navy) I always treat him to a nice cigar. I've come here a few times and the men have always been very helpful and my brother has always been happy with the cigars. Well last Sunday I drove from DC to Annapolis to have dinner with my brother. I called the shop around 6:55 and he said they close at 7. I told the guy about my brother and how I was planing to spend a good amout of money but I couldn't be there until 7:10. He said no problem he would just me cleaning up. I pull up at 7:09 and see a guy walking out and figured it was a last minute customer. I passed him and went to open the door and no one was in there. I looked at the guy as he got into his car, he must have known I was the one that called, and drove away. Two girls needed a refill on fluid and he said he was going to stay open for them too. It would have been perfectly fine if he said he couldn't stay open. But to drive off like that one minute before the time I said is not acceptable. read more

If I was in my 20's I would give this place 5 stars because it resembles something out of the movie Animal House. The owner Mike is a very nice person and is the John Belushi of the frat house. Really the cigar shop reminds me of a frat house. It is a tad disheveled and messy. Fun here is the ultimate indulgent as there is pretty much every kinds of TV, PlayStation, fish tanks, hookahs, food, drinks that a guy would want to enjoy his wallet on when he wants to self-indulge himself. Now remember I said this would be great if I was in my 20s, but guess what I am not. The atmosphere is great, but the place projects a certain level of laziness and uncleanliness that I would not associate with that often in my 40s. The humidor is rather large, but the humidor is very barren when it comes to containing cigars. Other than Rocky and Gurkha, I did not see many other name brand cigars in the humidor; this place seems to carry many boutique cigars. The display outside the humidor by the cash register is amazing featuring hand carved pipes, hookies, spices, sauces, lighters, really anything I guy could imagine. I believe I even saw a section of Chocolates and various flavored hookah tobacco. Overall I would give this place a higher rating as the shop keep (who claims to be a Reverend also) is an extremely entertaining guy who you can tell really enjoys his craft. The whole shop is a great size and even features a billiards table. Prices seem fair to a tad high but are in reason. Quality is a little lower on the other hand as 2 out of my 5 cigars I bought where too dry (probably due to not enough cigars in the humidor). The other big negative is the ventilation(or lack of a ventilation system as me and my 2 pals felt like coal miners when we left(my buddy had to run to get some fresh air during our visit as the second hand smoke was getting 2 him too much(and he is a weekly cigar smoker). The TVS are great and overall the CCC is a great place to have a bachelor party but not buy or smoke your everyday smoke. Defiantly the place gets a A+ for effort, a C+ for execution....worth a look if you have been boozing(did I mention it is BYOB)! Shop stays open for all the big football/UF games and has late hours which is also a plus! read more