Personally Selected & Expertly Curated

I get a lot of people asking me “You don’t carry ________?” With tens of thousands of cigar choices available on today’s market, we can’t carry everything AND, even if we did, it really would be a disservice to our customers.

You see, the average consumer has to make a whopping 35,000 choices each and every day. That’s a lot of decisions! Experts have identified that this burden of choices is causing people to experience Decision Fatigue.

Filling a walk-in humidor with rows and rows of closely displayed cigar boxes from floor to ceiling really does nothing good for the average cigar shopper. Packing yet another choice onto a shelf creates a backdrop where everything in front of you becomes mental white noise and makes shopping very distasteful.

We know, from research, that seventy percent of cigar buying decisions in a brick and mortar humidor are made right there in front of the box. If you can’t “see” the box because it’s just another face in the crowd, it makes your decision painfully hard.


Part of the unique experience of shopping at Chesapeake Pipe & Cigar is that everything we sell is personally selected by either Jonathan or I. I don’t just order whatever boxes of cigars that are household names or that have better margins. I smoke it (or use it in the case of non-tobacco products) and judge whether I like it and would buy it myself. Sometimes, that’s hard to do because it might not particularly be my cup of tea, but it is a solid product for that segment of customers that like that sort of thing.

This is particularly hard when it comes to flavored and infused cigars. I compare it to eating vegetables. I don’t like cauliflower, but I know there are lots of people out there that do. So, if I were a chef and I had to cook cauliflower, I’d have to taste it every once in awhile to make sure it was cooked properly. I don’t regularly smoke flavored and infused cigars, but I have sampled what we carry and can stand behind their quality 100% as if I did smoke them regularly.

A huge part of my vision for my humidor is to find great cigars that you might find hard to find elsewhere. Great representatives of various tobacco standards that you can’t get at the local liquor store or pro shop. Cigars that I personally enjoyed so much that I was willing to bet my limited personal funds upon because I know it’s a great cigar. I often tell people that “Before I ask you to buy a cigar, I’ve already personally bought it myself.” And, that’s 100% true. We’re not some big corporate group playing with a bunch of other people’s money. Every dollar we spend on products here at Chesapeake Pipe & Cigar comes out of our own wallets.


Over the last year or so, people have come out of the humidor and asked me if we were “Going out of business.” That’s their response as they see fewer and fewer boxes of cigars on our shelves. The answer is a resounding NO!

My goal is to display no more than 100 boxes of cigars in our humidor. Just to give you a little background, over our first 5 1/2 years in business, 95% of our regular sales (aside from limited editions) came from just 50 of the nearly 500 boxes we had on display.

Why? Because, in this world where we have to make 35,000 choices a day, less is more. In this case, fewer boxes of cigars with more information about what’s in that box, makes it easier for you to make a decision when you enter the humidor.

Using what some retailers would call a waste of precious shelf real estate to post a framed write-up about the cigars in the box next to it, gives you the snippet of information that you need to make a quick and comfortable decision.

So, we have drawn-down our available inventory in an effort to free-up open shelf space, reduce the number of shelves and make each and every box we sell easier to see — really see, not just make it part of an unfocused sea of boxes.

This process is an ever evolving “right sizing” of products I’ve personally selected to share with my customers. With fourteen awards as the best cigar shop in Annapolis, we have earned your trust in our taste. I often have people come in and say “You’ve never sold me a bad cigar.” Through our selection and curation process, I only hope that your next purchase from us is as good — if not better — the the previous.

Our job is to make your decisions easy and successful!