I Had an amazing time yesterday hanging out at Chesapeake Cigar Shop! @chesapeakepipeandcigar.com Spending time with my good friend Nelson, along with Mike, Rob, and several other great gentlemen, made for a truly enjoyable afternoon. I can’t say enough good things about Chesapeake Cigars in Annapolis—I’d give them an 11 out of 10! From their outstanding selection and fair prices to the welcoming atmosphere and incredible people, it’s an experience that keeps you coming back. And don’t forget—they offer a first responder and military discount, which is just another reason to support this fantastic local business. Looking forward to my next visit!

I was just passing through Maryland for a family function. Dr. Google suggested this shop for pipe tobacco and I am glad I listened. Spoke with the owner about various tobacco blends he was offering. Great guy! And great shop. If I am ever back in the area there will be a revisit! Thanks Mike!

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.

I visit this establishment frequently with the best proprietor of the finiest tobacco I have ever smoked in my life, along w9th fine recommendations if you are a frequent customer. Thank you.

This is long overdue. I stopped by on my way to DC. Honestly couldn't ask for a better spot. As a pipe smoker I particularly appreciated this spot. Picked up some plum pudding and a few house blends. Also picked up a phenomenal smoking Tsuge spider and Falcon. The guys working couldn't have been nicer. They even gave me a nice sample of a good aromatic and cigar. If youre in the area and dont want to deal with hustle and bustle of DC this is a perfect quit spot with an amazing selection of pipe tobacco. A definite must visit for anyone in the area.