Miami is known for its cigar culture. You can find a heavy heritage presence almost anywhere you look. There are numerous cigar factories, stores, and lounges spread throughout the city. Miami also has many cigar events that take place there, so we specifically wanted to focus on Destination HERF which took place January 11-14th this year. Caldwell Cigar Co. was the main sponsor, so we thought that we would sit down with Robert Caldwell, himself, and pick his brain on Caldwell Cigars, Destination HERF, and some exciting launches that you can look forward to this year. Some that may not have even been announced yet…


Jean: I’m so excited to chat with you! So nice to meet you.

Robert: Likewise. Sorry for the technical issues, but glad we are finally getting this interview done!


Jean: When I first started in the cigar industry, your cigars stood out to me on the shelf for their unique artwork. What inspires the direction you have taken with these?

Robert: I’m glad to hear that. Our brand is a very classical brand on one side and very contemporary on the other. I love cigars, primarily on the more mild to medium end of the spectrum. That flavor profile fell out of favor for a while, but it is making a comeback. When I started working on my brand, I wanted to make cigars that had this more classic approach to blending, while rethinking some of the flavors. I needed packaging that supported that. I have a lot of friends who are artists. We worked through a bunch of brand concepts, from names to colors to concepts, and finally fell on an approach that was meant to make your head turn. The packaging tells the story of the brands. It is a classic approach but completely rethought. 


Jean: You founded the Wynwood Cigar Factory, owned and operated The Hotel Humidor Company, and now have Caldwell Cigar Co. So tell me how you started in the cigar industry. What peaked your passion for cigars?

Robert: I started smoking cigars very young. I started with machine-made and smoked my first long filler as a punishment. I was caught smoking by my brother-in-law. He thought he would make me sick by having me smoke a big, strong cigar. Instead, I fell in love, even though it took me a couple of days to finish that first cigar. From there, I was off to the races. I was a regular cigar smoker for years before I got into the industry. I loved everything about cigars and still do. I’m a consumer before I’m a manufacturer. 


Jean: What have been some of your favorite projects you have worked on? 

Robert: Anastasia with Ernesto Carillo. He is the godfather. He has amazing tobacco, and I love his company. I really enjoyed working with him both to soak up his wisdom on the cigar side, but also I just really love his company. The other is Hit & Run with Matt Booth. Matt is as close to a brother as I could have. He is one of my best friends. We connect on another level. So, that project was fluid in a very unique way. 


Caldwell Cigar's Anastasia Caspia


Jean: And I know that you and Booth have a project launching in the first half of this year, so our readers should pay attention for that reunion collaboration. You have done some really unique and creative collaborations so far, is there anyone that you are dying to collaborate with that you haven’t yet?

Robert: Arturo Fuente doesn’t call me back. 


Jean: Do you have any upcoming projects that you can talk about with us today?

Robert: Yeah, why not? We haven’t announced it yet, but we are working on Long Live The Queen Maduro. I’ve spent about 15 months working on this blend, and it’s finally done. We are expecting this line to launch late winter or early spring. 

Caldwell Cigar's Full Line Up


Jean: Let’s switch gears for a second and discuss some of the community work that you do. I was impressed with the community outreach you discussed on your website. Can you elaborate a bit more on any of these initiatives?

Robert: We have done a ton. And continue to. We have worked with a variety of food banks, soup kitchens, inner-city education organizations, Toys For Tots, Tunnels To Towers, and many other groups. We have done all of these initiatives through the sale of our cigars. We aren’t very vocal about it because we don’t want to use our efforts as a marketing campaign, but we love being able to help. 


Jean: Bravo! It is amazing to see a company give back. So I wanted to also discuss Destination HERF. It’s coming up soon, and I see that Caldwell Cigar Company is the official title sponsor. What can you tell us about this year’s upcoming festival?

Robert: Really I would just say that you have to go to see what it’s all about. It’s an amazing event led by Jason Ferguson. It’s consumer-driven and consumer-facing. It’s the only event that I have been a part of that’s built by smokers for smokers. It’s a nonstop social event with amazing people that spans four days. It’s one of the few events that I really look forward to every year. 


Jean: This sounds like it’s going to be an amazing time! I wanted to wrap up our conversation with some questions I ask everyone. What is your favorite time of day to smoke a cigar?

Robert: Late afternoon. Halfway between lunch and dinner. So there is no time but there is timing. 


Jean: What do you like to pair with your cigar? Cocktail, wine, beer, coffee?

Robert: Room temperature water. 


Jean: It always seems to be an unfair question to ask, but what is your favorite cigar or.. if you could only bring three cigars with you on a deserted island, what would they be?

Robert: Anastasia Green Label Corona, First Production Davidoff Millenium Petit Corona and Illusione Rex. 


Jean: Robert, thank you again for taking the time to chat with us here at Cigar World. 

Robert: My pleasure, Jean, thank you!


To learn more about Robert and Caldwell Cigars, make sure to find them on social @caldwellcigars

Previous Article: Cigar World's Artisan's Corner: Meet Matthew Lange from Rough Sanded Woodworking

Cigar World sat down with Matthew Lange from Rough Sanded Woodworking to learn about his shop and woodworking creations.

Next Article: Cigar World's Artisan’s Corner: Meet Brad with Compass Woodworks Co.

Cigar World sat down with Brad from Compass Woodworks Co. to learn about the creation of his business and the influences that brought him into the space!

Join Cigar World Testing Lab


No one has commented on this page yet.