Cigarz On the Avenue

Cigarz On the Avenue has earned a serious reputation as one of the best cigar lounges in Winter Park, and people travel for it. Folks visiting from Fort Myers and beyond will tell you it's worth the drive, and locals count it among the finest spots for a cigar anywhere around Orlando. The walk-in humidor is the centerpiece here, big and well stocked, running the full range from familiar favorites to boutique sticks. On the shelves you'll find names like Padrón, Davidoff, La Aurora, and Bentley, and the prices stay fair.

Ask anyone who spends an evening here and the conversation turns quickly to the lounge itself. Comfortable seating, big clear TV screens, good air quality, and the kind of relaxed pace that lets you settle in with a stick There's a full bar too, and the whiskey selection gets talked about as much as the cigars, including some genuinely rare pours. It's a place that feels welcoming rather than intimidating, whether you've been smoking cigars for years or are still learning your way around. The staff is a big part of why regulars keep coming back.

Owner Don sets the tone, and names like Rich, Tristan, and Dan come up again and again from people who appreciate honest recommendations made without any pressure. Ask a question about any product and you'll get a straight, knowledgeable answer. As one regular put it, the crew takes the time to understand what you're actually looking for. We have heard the occasional grumble about a run-in with one staffer, but that runs against the grain of what most people experience here, which is warm hospitality and a genuine love of the craft.

If you're after a proper cigar shop and lounge in Winter Park, this one comes highly regarded by the people who know it best. Stop in, browse the humidor, and settle into a comfortable chair.