Local Lounge Exploration: Aiello’s Cigar Bar

In one of the many surrounding suburbs of the St. Louis Metro area, Cottleville to be specific,stands Aiello’s Cigar Bar, a beloved local cigar lounge where folks gather to enjoy a fine cigar and unwind. Aiello’s sets itself apart from other cigar lounges in the area with its unique bocce ball court, where they run lively bocce ball leagues that attract enthusiasts from near and far.

As you step inside, you’re warmly greeted by the friendly staff and a classic cigar store Indian. To your left and right, an impressive selection of cigars catches your eye, featuring renowned brands like Arturo Fuente, Padron, J.C. Newman, and more. The inviting ambiance continues in the back, where a few tables, a well-stocked bar, and a cozy lounge area with plush chairs and a TV showing whatever sports game is playing await. It’s the perfect spot to relax and enjoy the game.

Beyond the indoor lounge is a covered porch area leading to the bocce ball courts. Here, patrons revel in the fresh air and camaraderie as they engage in spirited games. The atmosphere is lively yet laid-back, making it an ideal place to spend an afternoon or evening.

I visited on a Thursday afternoon, and despite it being midday, the lounge was buzzing with activity. Customers flowed in and out, receiving attentive service from Andy, who graciously took time out of his busy day to chat with me about his father’s cigar lounge. Our conversation was a highlight of my visit, providing a glimpse into the passion and dedication behind Aiello’s.

Tyler: Let’s begin with how Aiello’s Cigar Bar got its start.

Andy: My dad is Joe Aiello and he started in a strip mall, and it was a Tinderbox first. He opened that up in 1997. We were there until January 2012, when we finally got this building fully up and running. We were still a Tinderbox for two more years until we bought out of the contract, and then we made it Aiello’s Cigar Bar.

Tyler: Now, I remember it being named Tinderbox a while ago. Why split from the Tinderbox franchise and strike it out on your own?

Andy: We were paying a percentage to the franchise, and we had signed a contract with them for a certain number of years but decided to get out early. It was Tinderbox at the old location; but at the old location, there was no bar and there was no bocce ball. At this location we have both. They wanted to collect a percentage on those, too. Well, there were no Tinderbox locations that had bocce ball courts, and very few had bars.

Tyler: That’s a pretty recognizable name, there aren’t a lot of Aiellos around here. Were there other names in consideration?

Andy: Yeah, there were a lot of other names passed around. One of the regulars here really liked “Wise Guys”. We had written a whole list of options. One was “Aiello and Sons”, which sounded a lot like an auto body shop and then I said let’s just do Aiello’s Cigar Bar. It’s our name and we’ve established ourselves with Tinderbox for so many years, so let’s make it our own name and sell ourselves in a way.

Tyler: How does bocce ball get incorporated into the Aiello’s experience?

Andy: Well, we are an Italian family. My dad was introduced to bocce ball by a friend who had a court in his backyard. My dad loved it, so he built one in his own backyard. When we moved to this location, he thought the only place nearby with bocce ball courts is The Hill (the Italian neighborhoods in St. Louis). So, we capitalized on that. We have leagues now and league play is great for business. Brings a lot of people in and there is nothing around here that is like it.

Tyler: How long has Aiello’s been at this new location in Cottleville? And have you guys seen a lot of growth?

Andy: So, we have been here for about twelve years. Moving to Cottleville was awesome. It wasn’t far from where we were already, so we kept our regulars, and we moved into a town that was growing and progressing very well. Yeah, we have had a lot of growth. It’s way better than when we were just in a little strip mall.

Tyler: How do you guys choose your stock? And how do new cigars or brands get introduced at Aiello’s?

Andy: It’s simple, we restock what sells. If something doesn’t sell for a while, we’ll make some space for it. Most of our stock is what comes from highly requested cigars. The ones that we bring in that sell well but are hard, like Opus X, Le Flor’s Andalusian Bull, are always in high demand. Really, most of what we have is highly requested. Probably the newest cigar that we’ve brought in is the Fat Bottom Betty from Drew Estate. And they sell really well here.

We even have the Fuente and Padron collaboration, Legends, in the humidor. The whole box is going for $7,115. That’s not an easy sell, but we know they are good cigars and that cigar collectors really love cigars like that. My dad is such a cigar geek, he might just end up keeping it if it doesn’t sell.

Tyler: Wow! That would be something to hang onto for sure! Now, I see that you guys have your own line of cigars here, how did that come about?

Andy: Oh yeah, Oliva makes those for us. Joe travelled to Honduras and picked out a special blend that he thought that customers would love. We started out with a Maduro, a Cameroon, and a Connecticut. We ended up sticking with the Connecticut; the others weren’t selling much, and we couldn’t justify buying as much as Oliva wanted us to order for each size and blend. But we do still have Connecticut in three different vitolas.

Tyler: What would you want someone who has never been to a cigar lounge to know or consider the first time come in?

Andy: If you are coming in to smoke a cigar, buying a cigar from us is a good courtesy. Buy a drink from us-it can be a soda, an espresso shot, or a bourbon. It’s just basic etiquette. Patrons can bring their own cigars, and we’ve seen people do that, but we also know they all buy from us as well.

If you are here, don’t get too rowdy; it’s a cigar shop lounge. Have as many drinks as you want, but there are other people here to enjoy a good time too. This is a family business. We may not live here, but treat it like walking into your home because you are kind of walking into ours. It’s really no different from a restaurant or any other service-based business.

Tyler: Your father is a big cigar geek and you have been around that for as long as you can remember and being around the cigar culture, what are some of the memories that you have?

Andy: I started working at the store when I was 15, but I can remember being 5 years old and my dad would have these parties at his house where all the regulars would come over and everybody was smoking cigars, and it was just a normal thing. I was treated as an adult at a pretty young age from being around a lot of these cigar smokers. When I started working at the shop, I was still treated as an adult and less like some kid working the counter. I feel like it’s made me wiser, more mature, and know how to act properly from being around older and respectful people all the time. I was pretty much an apprentice at this from a young age and was able to gain a lot of knowledge from all the different aspects of working here for the past 17 years.

Tyler: I would imagine, being around cigars all the time, you would’ve started smoking earlier on than most people?

Andy: Yeah, my dad let me have my first cigar about a week before I turned 18. I tried talking him into it earlier than that saying this is your chance to be a cool dad. He stood his ground and said “Nope, you’re not gonna have one.” Well one day I was working at the shop, and he stood up and came back with a cigar,  one of the Aiello’s we have. I smoked it and I couldn’t help but inhale it. And I kept inhaling it and inhaling it. He tried to warn me, saying “You’re inhaling it man, you shouldn’t do that.” On the way home I didn’t move a muscle and immediately threw up behind a bush at our house. That was my introduction to cigars.

Tyler: That was one heck of an introduction to cigars. Now that you know better, what are some of your favorite cigars to smoke?

Andy:  I love Fuente. Every day I smoke 858 Natural, the Hemenway, the Don Carlos, anything from them. Once I smoked a Cohiba Grand Reserva Siglo VI that someone gave me. I didn’t even look up the price because I wanted to smoke that unbiasedly, and it was a really, really good cigar. Montecristo No. 2s are also good. Partagas is amazing too. Padron is one of our best-selling cigars here, so that is a standard one I’ll go to now and then. Oliva Series V is also something I’ll pick up and light as well.

Tyler: If you had to define Aiello’s outside of just being a cigar bar, how would you define it?

Andy: It’s a place where there are a lot of friendly people with a similar mindset who just really like to chill. Great patio, bocci ball. It’s a place where you can come and get that great family-style costumer service. Yeah, that really sums it up.

After the interview, I took some time to relax and enjoy one of their house cigars, the Aiello Connecticut. It was a very enjoyable smoke that paired perfectly with a glass of Buffalo Trace whiskey. The cigar itself smoked beautifully, with an even burn and a smooth draw that never required a relight. The flavors, while not overly complex, were thoroughly enjoyable. This $6.75 stick would pair wonderfully with a great cup of coffee or a fine whiskey, enhancing the delightful atmosphere at Aiello’s.

So, if you ever find yourself about 30 minutes outside of St. Louis, Missouri, in the charming town of Cottleville, be sure to stop by Aiello’s. Enjoy the friendly hospitality, savor a fine cigar, and perhaps try your hand at bocce ball. And don’t forget to let them know I sent you!