At any rate, the trick is knowing where to find them and when to shop. While I can’t exactly help you with the timing — the idea there is just to keep an eye out and buy when you see prices drop — I can help by sharing where you should be looking. Most industry veterans and regular smokers are going to know about these places. This is likely a better list for the newcomers to the craft. Let’s light up and dive in.

Best places to find good cigar deals

Top Pick: Cigar Page

With most retailers, you’ll find excellent deals every once in a while, and okay deals often. With Cigar Page, you’ll find absolutely bonkers deals almost every week, sometimes daily. It depends on what you like and what you’re looking for. Most of their great deals are bundles, which include a variety of five to ten packs.

You’ll find every brand imaginable on Cigar Page, from your Cohibas and Montecristos to Graycliff, Florida Man, Warped, and Southern Draw. There is always a metric fuckton of samplers to choose from, for instance. You can also buy humidors, cigar gear and accessories, and some other items. There’s no chance involved either, outside of getting in on a deal when it’s live — it’s not a bid site.

Every purchase earns you Cigar Points, which is Page’s rewards program. You can turn those in for discounts. Every dollar spent earns you a point, and every point is the equivalent of a $0.01 discount the next time you buy. That may not seem like much, but if you buy often, it adds up.

Most Fun: Cigarbid

Owned and operated by Cigars International, Cigarbid is similar to eBay, except it’s all about cigars. You bid on items, mostly cigar bundles, and when the time expires, the highest bid wins. Now, there’s a trick to winning bids on the site. You might think they mark up those bids to make more money, but I’ve definitely won some, myself, that were ridiculously low. Too low, if you know what I mean.

Bidding at odd hours, usually late at night, helps. But sometimes, it’s just about being really lucky. I will say you should be smart about what and when you’re bidding. For example, look up the prices of the related cigars. If you’re bidding higher than what you’d pay retail, you’re just throwing away money, and sometimes it does happen.

You can also take advantage of Quick Buys, which is like the Buy Now button on most comparable sites. If you don’t want to mess around with auctions, that’s the way to go. Again, double check those deals before you slap your money on the digital table.

Most Reliable: Famous Smoke Shop

From its Monster Deals section, to regular everyday prices and great customer service, Famous Smoke Shop always deserves a top spot on my list. They have a fantastic selection of rotating deals on new cigar bundles and samplers, too. So, if you’re buying a gift for someone else, you can’t go wrong with a Famous sampler.

Always Good: Atlantic Cigar Company

Atlantic has some fantastic pricing year-round. I always check their site before I make a purchase elsewhere. They regularly offer prices lower than almost any cigar seller on this list. Of course, there is one well-known trick to shopping with Atlantic. You have to be logged in to see the best prices. More importantly, you have to make a regular purchase or two before you’ll see those best prices. Just one time counts, though, then you’re good pretty much indefinitely.

The funny part about that login stuff is that sometimes I’ll see a low price and lose my mind, forgetting I’m not even logged in. Then, I’ll log in, as you do, and bam, the price is even lower. It happens enough to where I’m always satisfied spending money with these guys. Shipping is relatively fast, and I’ve never had issues either.

Most Unique: Cigars International MMAO — Make Me An Offer

Imagine your buddy is cleaning out his humidor, only it’s more like a warehouse filled with cigars. Either they’re older sticks nobody really buys, the labels are being changed — like the recent Casa Carrillo swap — or they need to unload some stock. Whatever the case, your buddy is unloading and marking down his prices. That’s pretty much the idea behind Make Me An Offer from Cigars International.

You come in, pick a box, sampler, or bundle, and then throw down an offer. Someone on the other sides rejects it or accepts it, and that’s that. You can continue updating your offer as long as the product is available. So, if you bid too low, you’ll have the option to come back with another haggle. I actually scored a ton of Cornelius & Anthony boxes this way, for pretty darn cheap, before they were gone for good. I highly recommend checking it out every so often, as you never know what you’ll find on there.

Amazing Selection: JR Cigars

Between its rotating selection of deals, regular and huge inventory at MSRP, and also eclectic collection of humidors, cigar gear, and beyond, JR Cigars is a great place to go. If you’re a real budget hunter, I recommend checking out the brand’s JR Alternatives, most of which are made in name-brand factories despite their lack of affiliation. Rumor has it that Plasencia and AJ Fernandez are responsible for a few of those alternative labels. Wink, wink.

What I really love about JR are the stogies you wouldn’t find elsewhere. Boneshaker Full Body Cast, Samurai, Pure Origin: Gran Vulcano, Revival Series. The only thing I will say is that sometimes the brand’s marketing team does a terrible job at marketing certain proprietary cigars. They release a new cigar and don’t advertise it anywhere. That’s okay, more for me. But also why that matters, you have to remember to keep checking back often. Heck, you might even want to check now.

Some more places to find good cigar deals

Best Cigar Prices

It’s in the name. Unlike Cigar Page, which focuses on a lot of one-off samplers and deals, Best Cigar Prices tend to include a persistent series of deals. They offer everything from Fuente and Rocky Patel to Oliva and Padron, with rare cigars in the mix, too.

Cigars Direct

Something you’ll notice with Cigars Direct is they have a strong focus on select brands. Now, allow me to clarify. It’s not that they don’t offer an excellent selection, because they do. However, especially if you sign-up for email alerts, you’ll notice they rotate deals around focusing on one or two brands at a time. That means you won’t be inundated with choices, keeping things a little tighter. But, it also seems like they’re able to offer some pretty unique and incredible deals as a result.

Cigars dot com

Not to be confused with cigar (no plural) dot com, Cigars.com offers some reasonable deals now and then, just like its sister site, JR. You’ll also find a lot of popular brands on here that buck the norm. Some examples include Illusione, Caldwell, Tatuaje, Drew Estate, Padron, La Flor Dominicana, and a few others.

Gotham Cigars

“Premium cigars at a discount” is pretty much the tagline for Gotham Cigars’ entire website. You will find some great deals here, but you’ll stay for the great selection. Gotham also sells nicotine pouches and a wide variety of small and flavored cigars.

Smoke Inn

I actually got in trouble with some cigar guys for including Smoke Inn, on a round-up for another media outlet. Apparently, they didn’t like the selection available, and they chewed me out. Screw those guys. I’m including Smoke Inn here, and again. They don’t offer everything, so it’s not a place to find every brand you’d ever want. However, there are some excellent deals available from time to time, especially on bundles and samplers. Not that it matters, but Smoke Inn also sponsors a lot of different people in the community — like Kevin Shahan from Cigar Prop.

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