Cypress Cigars

If you're looking for a cigar shop in Winter Haven where you can actually sit down and enjoy what you buy, Cypress Cigars has been the spot since 2006. The heart of the place is a large walk-in humidor stocked with everything from the newest releases to the classics. On the shelves you'll find names like Arturo Fuente, Alec Bradley, ACID, Aging Room, Alfonso and 20 Acre Farm, and locals will tell you the selection runs from common favorites to harder-to-find sticks across just about any price range. The cigars are kept so well that they often show a little plume, which is the kind of detail people who know their cigars notice right away.

Ask anyone who shops here and the name that comes up first is Tom, the owner. He greets folks the moment they walk in and remembers them by name, and regulars trust his advice completely with picking out a smoke. His employee Jeff gets the same kind of love around town, known for being easy to talk to and happy to help you land on the right cigar. The word around Winter Haven is that this is a place where you make friends.

People come in daily, settle into the comfortable seats, catch something on the TV, and strike up good conversation over a cigar. The new location leans a little more upscale, with room to kick back and smoke inside, plus coffee, soda and water on hand if you plan to stay a while. One regular summed up the appeal by calling it the best cigar shop he'd ever been to. We'll be honest and say a few folks have grumbled that certain boxes run a bit over retail, but that's a small note against a shop this well regarded.

With close to a perfect reputation and years of loyal locals behind it, Cypress Cigars is one of the highest-rated cigar shops in the area, and it's the kind of place where you go for one cigar and end up staying an hour.