City Cigar by the Bay

If you're hunting for a hard-to-find cigar in Miami, City Cigar by the Bay is the shop that keeps coming up. Locals will tell you this spot on the Regatta Harbour property in Coconut Grove has become a real favorite fast, sitting right by the marina with plenty of parking, a couple of bars and restaurants nearby, and food that can be ordered and delivered straight to the lounge. It is already one of the highest-regarded cigar shops around. The name everyone mentions is Tommy.

Ask anyone who shops here and they will tell you he is the heart of the place. People describe him as patient, warm, and genuinely knowledgeable, the kind of tobacconist who takes his time helping you pick the right cigar whether you are a weekly smoker or walking in with no clue where to start. One visitor showed up to buy a gift knowing nothing about cigars and left with a story to tell, thanks to Tommy rolling up with his cigar cart and turning it into something fun and educational. We have also heard of him tracking down a rare cigar for someone vacationing over in South Beach who could not find it anywhere else.

The walk-in humidor is where regulars really light up. Word around the Grove is the selection runs deep and covers all levels, with a strong lineup of Padron, including some rare ones, plus Atabeys that are tough to get your hands on locally. Beyond cigars they carry the smoking accessories you would expect to round out your humidor. The lounge itself gets just as much love.

Comfortable chairs, a TV, indoor smoking, and a crowd of aficionados from all walks of life who make newcomers feel at home. As one regular put it, they came in to smoke one cigar and stayed for three. Sophisticated but never pretentious, it is the kind of place you settle into for a good conversation and a top-shelf smoke.