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Chesapeake Cigar Best of Annapolis

Photo by Scott Lyons

The cigar lounge is an inviting place, a sanctuary where people go to relax and enjoy a fine cigar. My cigar experience began when I visited the new cigar shop next to my place of work. Although my cigar knowledge was limited at the time, I was drawn to the culture and relaxing atmosphere. On a recommendation, I smoked a Montecristo White and my love affair with cigars began.

Having earned a degree in economics at the University of Maryland, I spent nearly two decades in the mortgage business. While I enjoyed solving people’s problems and serving their needs, it was a really frustrating business. After leaving that industry, I served as a technology consultant and business manager.

As chance would have it, an opportunity opened for me to work in that same cigar shop where I took my first puffs of a quality cigar. My decades of experience in sales and customer service gave me the skills to grow the business and I quickly moved from part-time employee to shop manager. As I learned more and more about cigars and the people that smoked them, I formed a fine-tuned vision of what a great cigar shop could really be; a balance of cigars and accessories for sale and a comfortable, welcoming place to smoke and, most of all, relax. With this vision, and the support of my wife and partner, Connie and the encouragement of our family and close friends, we opened Chesapeake Cigar & Tobacco Company in June of 2009. In October, 2016, we moved to our new location on Old Solomons Island Road in Annapolis and created a LLC. Our name officially changed to Chesapeake Pipe & Cigar LLC at that time.

We founded Chesapeake Pipe & Cigar on the simple idea that you should be able to enjoy a quality hand rolled cigar or fine pipe tobacco anyway you’d like. Whether you stop-in occasionally and buy a few cigars for a golf outing or become a regular in our spacious smoking lounge, we are here to help you make the most of your pipe and cigar experience.  I firmly believe we’ve found the perfect balance between being a retail tobacconist and a sanctuary for cigar smokers of all walks of life.

Voted the Best Cigar Bar by “What’s Up Annapolis” magazine just six-months after opening, we continue to fine-tune and evolve in our quest to be the premier destination for quality pipes and tobacco, hand rolled cigars and the best culture in Maryland.

— Mike